I often find myself envying women who can pull this look off – whereas I think that Iook like a bag of potatoes when I try oversized clothing. But I think the only secret to look good in oversized clothing is to make it look intentional, and somehow I’m not there yet.

I wonder though: Does this look work better with clothes that flatter your figure, but in a larger size, or with something that doesn’t flatter you but is bigger than it should be? For example, if Garance Doré’s jackets in the pictures were her actual size, would they flatter her?

I think three factors come into play here, and you probably need all three boxes ticked to make it really work:
- context (Garance is a fashion photographer and style blogger)
- somehow being able to make it look “intentional” (that often means having the rest of the outfit be “exactly right”)
- and last but not least, having the confidence to pull it off (

I really appreciate the look when it’s perfectly executed, but for me personally, good fit and Kendall’s philosphy have done wonders more often, so I think I’ll stick with that:-)

That’s what I love in new trends , and new way of wearing clothes.

People don’t try to be like everybody, they accept themselves ! There is also the fact of the society accepts easily differences , and creates a look for everyone !

http://www.elitebarcelonablog.es/

We love your blog

So true! This season I saw a lot of loose coats and jackets.
It’s depends on your body, some body types can pull volume around the hips, others don’t, but don’t reject an item based on just that!
The key is to try everything!
Last year I learnt I could pull a loose dress! Imagine, an houglass with a D cup!

IMO you need to have an arty edge to your style to do that, be confident and non-frettable about how it may flatter your body, accept cool over figure-flattery and unfortunately ( or maybe i just have my body hang-ups) be quite conventionally slender, as to create contrast between the small frame and the over sized garment. All the fashion bloggers I know that are of fuller size wear great fit. The ones of the slender spectrum sometimes wear over sized. I think it’s a look , very arty and cool, but not very wearable daily. Even the coolest artiest hippest gal wouldn’t wear a three size bigger coat to a law office.

I agree with Inge about making it look intentional. In the example, Garance makes it intentional with the belt she used: it’s different from the coat, it’s supposed to be noticeable, and to my eye, adding the belt means she isn’t drowning in it at all.
To me, it makes the world of difference than if she had just buttoned the coat – then she would have looked like she was drowning, the silhouette would have been totally different. As it is, she is wearing the coat, rather than the coat wearing her.
Intentionality is key.
Also, maybe the item itself might matter. You can intentionally wear a dress that is too big in the bust – to make whatever statement you want. But take the coat in the example: we are supposed to wrap ourselves in a coat to keep warm. That the coat is too big, but belted, tells me it’s cosy, comfortable, casual. If it was a dress that was too big in the bust, no amount of belts would help.
Now that I’m thinking about it, maybe it’s a combination of both intentionality and the item: whether it’s possible to have it look intentional (eg by belting, scrunching sleeves, playing with the proportions of the rest of the outfit etc.)
Sorry this is rambling, I’ve had no sleep!

Maybe you can do the cool stuff where your physical assets/positively distinctive features are?

Garance is slender, so the coat is rather rich than overpowering. I have long and shapely legs so could pull off all kinds of interesting tights/stockings and crazy trousers if I wished to, as well as broad shoulders that allow me a lot of leeway with my coats and jackets. I shouldn’t try anything fancy around my waist.

But I think you have to develop a kind of artist’s eye to determine whether something ill-fitting adds to your overall picture. And sometimes you have to balance that bad fit with another item that restores proportion.

Harem pants come to mind as ill-fitting (as in not enhancing body form) by definition. Some pull them off, some don’t.

Very interesting post! I agree with the others about intention, context and body shape. I also think it is important when you were an oversized not-fitting-in-a-conventional-way garment that everything else fits. A too big coat worn with too big trousers and too big shoes wouldn’t work, for example. Also, sometimes when I look at fashion bloggers, I think their outfits also are about experimenting, trying something new and being creative, and that these outfits may not really work that well if I saw them on the streets.

For me, Anya’s comment nailed it all. I dress this way a lot stemming from memories of being that slender young woman. I like that look of Something About This Garment Grabbed Me and I threw it on and continued on my way. But it sure doesn’t work for
heading into a law office or anywhere where you are supposed to look like you respect the occasion and other people’s reasons for being there – a Polly Bergen concept.

I’m pretty sure intentionally ill-fitting clothing is a “luxury” reserved for skinny young things with perfect bodies. Someone like me wearing an off-sized item would be judged entirely differently. Also, swimming in a big jacket signifies something different (wrapped up to keep warm, or even, hey, I’m wearing boyfriend’s/daddy’s clothes, isn’t it cute) than wearing other clothes that are ill-fitting. And wearing clothes that are too tight doesn’t work on anyone with the slightest imperfection because it just looks like you are trying to squeeze into something that you grew out of and our society judges “too-big” bodies (even if just a size 6 wearing a size 4) so harshly.

I like the intentionally “shrunken” jackets that have been around for the last few years more than I like the over-big boyfriend looks. But those have to actually fit — they can’t truly be ill-fitting in the sense of being the wrong size.

I think an important factor in this particular example is that the coat she is wearing is not actually too huge in the shoulders and arms, and it has a lot of inherent structure. It wouldn’t look as cool with a droopy fabric or sleeves that were hanging way down past her hands, I think.

Along with what everyone has said, I think looking cool in a bad fit requires an excellent understanding of what is a truly good fit on your body. I would be happy enough just to master that.

Angie hits the nail on the head when she says it is the “style savvy” who are able to break the rules of “fit”. When one has perfect mastery of form one is able to successfully break the rules.

To me personally great fit always triumphs. I think even a slender, fashion forward blogger would wear that look once or twice and then the garments would end up thrifted/no worn again HOWEVER great fit is forever.

It’s not a look I care to emulate, and I think in most cases fit trumps “cool.” That said, I think you have to have a certain personality, body type and other physical characteristics to pull something like that off. Whenever I buy clothing, I consider not only what I’m drawn to, but also what I think will work with my body type, my facial features, my hair, etc. Everything has to blend together into one cohesive look. I don’t know if what I’m saying makes sense or not, but I believe that’s the reason I’m not able to pull off certain garments, while others look fabulous in the stuff I look horrible in.

Angie this is so my biggest lesson from you. I did feel that if clothing was a bad fit it was me that was at fault, also that if I just took a deep breath and squeezed in to something it might work. All wrong!! Now I spend ages finding the right fit for me.

Lol I did think I was made of spare parts! petite on the top half but needing extra long on the bottom half.

I like the look of the boyfriend jumpers/ tops but the proportions still have to be right .

Thank you for just one of the lessons I have learnt here

I would love to pull this look off and think it looks super cool on a fashionable arty slender person. I think I’m too old, too less than slim and too uncool, but I can accept that. Besides I did this look in college with Goodwill men’s overcoats and blazers and leggings. (I felt cool then – probably just looked disheveled, but that was college. I’m now at a stage where I want to be more classic and need to work on fit. Having lost a lot of weight and gone through the awkward period of your clothes being too big (while trying to recreate an entire wardrobe) and trying to squeak by pretending it’s intentional this no longer appeals to me.

I really enjoy this look when done well, and others have mentioned some key details that contribute to being *well* done: intentionality, slender body type, context, confidence. Plus Mander’s observation about how the shoulders and arms aren’t that oversized is very astute. There is nice balance with her other garments and accessories being more traditionally fitted

I like the nonchalance, or ‘cool’ it projects, and I see this as one form of artistic dressing.

My imaginary self (the 5’10″ willowy one) would definitely be wearing this look. My real self (the 5’5″ NOT willowy one) mustn’t go there!

JJsloane – I think we must have been students at the same time! I wore a blazer from my dad, leggings and Dr Martens and also felt very cool back then!

I agree it takes some style savvy to pull this off well. I do love a big, slouchy sweater over skinny jeans but I am not sure I am making a style statement when I do it!

I agree with Inge and Anya. Location also helps. Some of the outfits on The Sartorialist and other blogs would stand out in my town, and not in a good way.

I think the oversized look can work if you;re tall and willowy – I’m not so sure it’s a look that can be achieved successfully by the masses though. For me, I would just look like I’d chosen the wrong size or robbed someone else’s closet. Gosh, I’m just learning about PROPER fit!

To me, this has to be done to perfection for it to work. And even then, some will like and others won’t. I love the Garance picture.

It reminds me of when I was in school studying a Hemmingway novel. Some of the students indicated to the prof that Hemmingway was not writing according to the rules that the prof was teaching us. The prof said you can only break the rules once you have mastered them.

I think that fit is contextual, and dependent on intent. If the jacket in the Sartorialist link fit the way we’d normally expect, the look wouldn’t be what she’s intending – and *that’s* bad fit. The jacket in the picture actually ‘fits’ perfectly.

Think about boyfriend wear. If you put on a boyfriend jacket and it fits like a glove, that’s a bad fit, even if it happens to look great. Good fit for a regular look, bad fit if you’re going for a boyfriend look.

Slouchy trousers are a good example as well. If your eye dislikes the look, slouchy trousers appear to be the most ill fitting garments imaginable, but if you like them, they seem just right. And from the other direction, if you put on your trousers intending for a regular fit and instead they wind up a perfect slouchy look – that’s bad fit! Change your intention, and the ideal fit changes along with it.

Thanks for your great thoughts here, ladies. I’m thoroughly enjoying reading them. Astute!

Mander, I think that in the first photo, the shoulders of the jacket have been pulled in “to fit”, which helps the look. In the second photo – not at all and nothing about that jacket fits. In both photos the sleeve widths are ill-fitting.

Girl X and Rute, the fits of BF jackets and waist surrendering dresses still have structure and fit in all the right places. Those are different animals in my book and I hope that makes sense.

Inge, Anya, Sona and Sigrid, your comments really resonate with me.

I’ll add that wearing one badly fitting garment per outfit helps create the intentional look.

Well i’m guilty of wearing clothes that are too big. When i’m thrifting i don’t pay *that* much attention to size. Just throw it in my cart if it catches my eye and try it on.

I think quite a few things contribute. I feel that if you have something that is dramatically oversized the rest of you outfit needs to be spot on and well fitting. Scrunching or rolling up sleeves, tucking in or doing the 90s tie to shirts certainly help make it look like you belong in the top.

For bloggers i think they have a few more helper on their side. Knowing how to pose with an oversized whathaveyou and having good camera angles taken. This recent blogger outfit post comes to mind: http://www.fashionsalade.com/j.....ssssss.jpg
And last yes, being slender and good looking.

Garance has youth, extreme thinness, a casual/groovy job, an artistic eye, confidence that she is gorgeous, and a certain French je na sais quoi. You can pull off anything with these factors – even that coat. But remove one and I think you become a hot mess.

I wonder how much having a camera around her neck helps Garance pull off this look. It is definitely an arty vibe and the camera screams artist. Imagine her holding other objects..a briefcase, a reusable shopping bag, a toddler…do you think she would give off the same vibe? Or would she just look like she’s wearing an ill-fitting coat? A camera is not normally considered a fashion accessory, but maybe this time it is.

I agree with SuzyCue on the camera as accessory. I would add her hair, glasses and great expression, too. The coat is almost secondary. My eye would see something completely different without these elements.

Whatever Garance is doing, it works and I like it. I think Suzycue is right on with the camera being an important component in making the outfit work. Confidence and intention are essential, too. Thanks for another great lesson today, Angie.

I like that look, remains me of the eighties . . .

I think the most important thing with this look is that it has to look intentional and done with confidence. I’m sure it doesn’t hurt to be tall and willowy either!

Intriguing! I think the key to this look is that it’s effortless. Not unintentional, but effortless in the sense that you instinctively put on the ill fitting item sensing that it will work with your outfit. I don’t think you can “make it happen” by trying hard. This works on someone who has a highly evolved sense of personal style and great confidence.

I wish I had it

I agree with what everyone else has been saying here, this definitely would not work in non-artistic settings. I’m imagining having to give a talk at a scientific conference in anything “oversized but cinched in with belt” and can’t believe I would be taken seriously. Overall I do like this look a lot though, but am not confident I can pull it off despite being skinny. I have a small frame and oversized clothes quickly become overwhelming and I look like I got dressed in the wrong closet. I also think it works because of the belt, but frankly wearing a belt over anything without belt loops drives me insane. I’m fiddling with it all day and feel self conscious, like I’m trying too hard. Which would defeat the point of this look (nonchalant, look what I just threw on!)

I actually love this look when well presented as in your examples. As with anything that makes a statement it must be done to perfection with all the key elements just right.
I would love to pull this off but it really isn’t my style so I will admire it from my extreme tailored bench.

Great post, Angie, and a really interesting question. I love the look when it is done well, but fear I did it poorly too often in the 80s to do it very well now myself! And I love the feel of well-fitting clothes. Having said that, if I saw the perfect piece, I might try it. For me (being on the small side) that piece might be difficult to find; I could easily be completely swamped by too much fabric.

This is something I admire on other people but have never been able to pull off myself, or maybe I just don’t feel comfortable with the look on myself. I think I play around with this concept to some extent by my focus on slouch even though I have a small frame, but it is always a fitted slouch, not just something a size too big. I think pulling off a look with misfitted items like these takes a special talent.

Mmm. They say fashion comes from the street. When you’re “from the street,” you’re getting hand-me downs, charity shop finds, etc. Lot’s of things don’t quite fit right. People come out all the time looking stylish without sewing.

It seems to me, mulling it over, there’s a difference between putting on a belt to get something to stay on and putting on a belt to make something “fit,” which is what I think Garance has done. There’s drowning in a too-big shirt and merely rolling up the sleeves; then there’s, say, cutting the neckline so you get an off-the-shoulder number.

It may also have something to do with being able to function properly, without the clothes getting in the way or being bothersome.

I truly think that in the case of fashion bloggers we are looking at a photograph. But I think that when the person in real every day life is moving, sitting, standing and doing all the normal every day tasks, then the ill fitting clothes will be just that, ill fitting.

More interesting thoughts!

Suzycue, I think you’re dead right about the camera. It’s as if the camera gives the outfit a right of passage.

Dany, I had the same thought as you a moment ago. Sometimes an outfit can look so much better in a photo than in motion. And the converse of that is true too.

Taylor and Inge, I too admire these types of looks on others. For sure! In the same way that I admire any type of stye that is well executed. There is no one way to be stylish and that’s so very liberating. But Good Fit is where it is at for my style – and that includes well fitting waist surrendering styles, boxy blouses and dresses, slouchy trousers and oversized blazers.

For the record, I will boldly say that Good Fit *does* trump it all because it has longevity AND an sense of effortlessness that cannot be beat.

I think you have to have a very thin and straight body type for this to work, plus be arty or edgy, worn in a fashionable context and youth and height helps. It also has to be big enough to look very intentional.

I love this look! I think Garance looks amazing! Another blogger who consistently pulls off this look is Beth Jones of http://www.bjonesstyle.com/blog/. But I also agree that context is everything, this is a very specific look, and it helps to be obviously artsy, young, tall, slim, and conventionally beautiful. For mere mortals such as most of us here at YLF, great fit is always going to be a better option!

Guilty! I’ve ALWAYS loved the intentional ill fitting look. It’s why I adore slouchy trousers, oversized sweaters, baggy Levis, old army jackets – it’s all a throwback to college for me, of course. And they can have that sort of devil-may-care tomboy panache, like wearing your boyfriend’s shirts.

Since YLF, I’ve realized I’m not well suited to pull off most of these looks – although I have the requisite recklessness/lack of fear, I can’t look at myself in them in quite the same way. Now I mostly save them for the cabin, where there’s no mirror, only my imagination and second-hand clothes!

I agree that it has to look intentional and mostly only works on tall, super thin, young girls. (and maybe boys, too). I know for me, I’m the most comfortable with clothes that fit. I can’t pull off the more “sloppy” look.

Agreeing with those who say this style works best on a rectangular, tall, relatively slender body. I remember going shopping with a hs friend who was so tall/thin that the dresses in her size weren’t long enough for her. She could easily rock this type of outfit. For a non rectangular figure, the extra volume is too much.

Kendall’s quote on on fit is perfect: “Good fit is the equivalent of six months in the gym” and my first impression is that while it works for Garance, it wouldn’t work for me. She has the cool factor, which is stylishly acceptable. In fact, I love her in the photo shooting the ice cream cone with the fedora, over-sized jacket, nice legs, cute gray purse and wonderful black flats (oh, I LOVE those!). Instead, I would just be swimming in fabric and looking frumpy. I think her profession makes all of this work, both from style and necessity.

Thanks for expanding your thoughts on this Angie!
REALLY being able to appreciate and admire different styles often so far from my own is really a gift I have learned right here from you and YLF.
Thanks:)

I will go back and read the comments after I post, so I hope I don’t offend anyone…

… but I have *such* a negative reaction to grown women who purposefully wear ill-fitting clothes to look cool. Young girls, fine. Maybe they don’t know better or don’t have the $ to find a proper fit. But to me, that Sart pic just rubs me the wrong way as being overly contrived and perhaps a bit snooty. “Oh, me? I’m SO tiny that everything is just TOO big, and I’m SO rich and SO much more evolved that I can afford to toss money around and buy ill-fitting clothes for fun.”

I admit: I am possibly biased because I once WAS that kid that had to wear ill-fitting clothes for lack of money. The resentment I feel is probably quite disproportionate.

I too like this look on some body types. Generally really thin frames. The rest of the outfit needs to have a more relaxed style with an artsy edge as well. I used to intentionally wear baggy straight-cut jeans when I was a size 4 and really thought it looked better than fitting jeans. Sometimes baggy balances out proportions better.

I’ve noticed this trend on young-ish style bloggers (The ManRepeller pops into my mind first), professional models, and my 11 year-old daughter when joking around in my closet. Honestly, people are fully entitled to wear anything they like (provided it’s acceptable for their environment, and I’m assuming people like style bloggers have free rein), but I see more of an “The Emperor Has No Clothes” effect here. Sorry! I’m sure it strikes others as cool and oh-so-chic, but for some reason to me it strikes as ‘haha, won’t I be the envy of all the minions watching me! I’m too cool to follow fashion rules!’ *ducks*

Garance looks great but I agree its the camera that pulls this off. Its a very 80s menswear look and you need to be very thin to pull it off. She looks fabulous though its just not a trend I would want to pull off. I need the tailored clothes to look like I’ve been at the gym for the last six months

Rae, I tend to have the same reaction to Garance but I think it’s because I know way too much about her personal life…

I am with Rae. I don’t think it looks cool at all. And, honestly, I don’t think anyone really “pulls this off,” as in, looks good in it. Some just don’t look as bad as others.

Hmm. That coat is “fauxversized.” The shoulders fit and the sleeves aren’t baggy, so I would say that’s a very carefully tailored contrived “look,” not just wearing a big jacket.

You’ve got to be kinda petite and cute to get away with this, I think, not a tall athletic build like me… I’d scare people.

Everyone has been saying that this works for Garance because she is young. I agree that being very slim and hip helps tremendously, but she is not extremely young–37 or maybe 38 now.

Agreeing with much of what has already been said. Every piece of the outfit needs to be very intentionally chosen, it doesn’t hurt to be tall and very slender, and I think the pieces need to be of very good quality for this look to be pulled of well. I also wonder about Amanda’s comment about “fauxversized” hmmm, she could be on to something.

Rae, that’s an interesting and candid point of view.

Helen, no need to duck! Your perception is meaningful and it makes sense to me too.

Taylor, thanks for chiming back in. If you take an interest in fashion and style I personally feel it’s important to appreciate styles that are very different to your own. Our style experiences seem richer that way.

Velma, I do believe that Garance is in her lat 30s and actually quite tall.

Amanda and Queen Mum, I commented on “fauxversizing” in my previous comments here (to Mander and Girl X). My point of view is quite the opposite. We all see different things, don’t we!

It’s a cute look if you can pull it off. I can’t but I do appreciate it on others.

Very interesting. Like Inge, I think I’ll stick to well fitting clothes – that’s enough of a challenge for me It is a very intriguing question though – I think how you carry yourself is key – do you like the look, do you like yourself? That will speak volumes. Also, like Inge said, I think you’d have to have the rest of the outfit really well structured and pulled together. Lastly, I think if the rest of the outfit is somewhat edgy, I think that makes a difference to my eyes.

Angie, Love this topic as I think it is the crux of why so many women feel they don’t look in clothes or can’t wear a particular item. Very few people can wear garment “off the rack” and look fabulous!

I deal with this all the time in my business and I am just starting to see women really take in the concept of tailoring. I think it was a few years back that we began to share what I call the “Hollywood Red Carpet” secret—that all those fabulous bodies were not as svelte and perfect as we thought. For many garments, pants especially, these pubic profile women wear/order a size up and then have some minor tailoring done to take away the “back gap” or “pouf” at the seams. I usually tell my customers that they should order the size that skims GRACEfully over their “hot spots” which, for most of us, is the thigh, tummy and possibly bust area. Then, take it to your tailor for a simple alteration that will make it look as though the garment was made for YOU! Not only will the garment then look great, but you will feel great knowing it’s not pulling, pushing, straining and that your clothes are beautifully draping you. Not sure if it’s the additional cost of altering a garment that we perceive is “not worth it” or if it’s the inconvenience and not having the patience to wear it when it’s perfect.

We are all built differently and uniquely and I always feel sad when a woman laments that “nothing looks good on me” or “I don’t look good in clothes”. Anyway, off my soapbox, but minor alterations make a huge difference and I want to scream “you’re worth it!”. We are our own worst critics—luckily, we can fix that!

I will reluctantly say that this only works on very slim women, a group that does not include me.

I read the Ines de la Fressange book, and she recommends every woman wear a velvet blazer that is slightly too small. I tried this and it looked terrible. I think it made me look larger than I am -two pounds of sausage stuffed into a one pound casing.

Just today I found a velvet blazer that fits perfectly, and I feel so much slimmer in it! I wouldn’t feel as good with it oversized, either. So I agree with you, Angie, about fit.

Angie and Taylor: I had a feeling our Good Fit views would be very similar, and I see where not alone here:-)

At the same time: hurrah indeed for the millions and millions of different ways to be stylish!

I think confidence has a lot to do with being able to pull of this look. For me good fit is all important as I think it flatters my figure more. I hate to say it but generally I think a slender person can work this ‘ill fitting’ look best as it doesn’t add too much to their frame. For me being short and large busted, it would take a lot more work to achieve the look without it adding a huge amount of bulk to my frame. Having said this, I do love the look and I always find Garance to be incredibly stylish.

I’m not sure what the guidelines are for taking ill-fitting to cool but I like it when I see it done well. And I also came from a pre-YLF style of wearing too big, ill-fitting, not cool clothes. So I’ll stick to continuing to work on good fit and leave this advanced style technique to the experts.

I do not aspire to wear anything that is ill fitting. It goes against my grain, my “training” and my inherent style. I can enjoy it on someone else, but, no, not for me. Very few can make this work.

Hmmm…I really like the look of oversized, loose, don’t quite fit clothes, on women and men. Especially in fine materials (silk, wool, cashmere) I think it can look very chic. I certainly prefer too loose clothes to too snug clothes, hands down. And I 100% don’t think one has to be skinny, young, beautiful, a rectangle, etc. etc. to wear loose clothes. Looks like I’m in the minority here .

Very interesting. I LOVE LOVE LOVE clothes that fit well! It is something I have learned as my style has evolved and as I have gotten older. When I was young I, like many of us, could wear almost anything and look fine. Baggy overalls, super short wind shorts, t-shirts, …etc. I believe when you are young you can experiment with all different styles and fits. For me, as I got older those free-wheeling styles didn’t work any longer. I now have to pay a bit more attention to my clothing, especially the fit, to achieve the casual, yet put together and elegant style that I am going for.

Fit is huge for me and when I am wearing something that fits well I feel great and I know that it looks great. I often mentally make people over in public, tweaking their fit here and there…

That being said, I always appreciate the brave soul who attempts to pull these looks off, whether they are in movies, print, or real life….

Such interesting thoughts and opinions make for a great read! I’m on the team that believes good fit trumps all. The “cool” factor I can appreciate on women and girls who are tall, slender and at least look under 30 and live an arty lifestyle. But even they would probably look better in real life (not just a photo) wearing a good fit.

I didn’t think Garance’s outerwear was “ill fitting”. That term has a negative connotation. I thought her jackets were roomy and allowed for wearing ease with sweaters underneath. They look great on her, and would work better for her work than some tight, tailored coat.

I love the attitude of this look, in my opinion it says I love this item so much I don’t care about the rules. It is rebellious in a way that whispers rather than shouts. I have to say I much prefer the oversize trend to the ‘I bought my blazer at Gap Kids vibe’.

I think the look is really great on very thin bodies. If you’ve got curves, I think it will only add weight or create odd proportions that just won’t look flattering.

But I do really like the look…just not on me! I think I admire it so much because I was a teen-ager during the grunge years in Seattle, when this look was everywhere! Nostalgia….

I found your post via The Beheld, love your blog!

I was actually thinking about this the other day when I saw a photo of a baby wearing an adult-sized cowboy hat that was adorably covering one of his eyes. I wondered why that made it so much cuter and realized: the inappropriate fit brings attention to the tininess and non-cowboy-ness of the baby. So an over-sized article of men’s clothing on a petite or slender woman brings attention to the fact that she’s not big or a man. Then the rest of the outfit should scream, “little woman!” to play up the contrast. I guess Marilyn Monroe wearing her floppy blue sweater with tights in “Let’s Make Love” would be an example of what I’m talking about?

Or to go in the opposite direction, I remember in the mid-late 90′s grown women started wearing little boy’s t-shirts that didn’t adequately cover their torso and it brought attention to the fact that they’re grown ladies with lady-bodies.

Even in the Jackie-O era sixties, when I think of tailoring and fit as standard in women’s clothing, the proportions were still weird because women made their hair and eye makeup enormous and wore little gloves that cut the line of the arm short. They looked so doll-like, it was almost like the adult human body WAS an inappropriate fit.

I don’t post often, but I really have to come out in defense of the baggy. I personally am a sucker for all things supersized, menswear and the looser fit. It’s fantastic for layering in the winter, it’s cool and breezy in the summer, and done right, it can look very striking.

But I admit, it is a very difficult look to pull off. I know this from bitter experience, and I don’t always get it right. I personally think oversized pieces can work on more or less any body shape, but you have to be on the look out for two things.

1. Proportion. Bigger pieces have to be balanced out somehow. For instance, an oversized shirt can look great tucked into a pencil skirt, or belted over leggings or skinny pants. An oversized coat can be belted, or worn open over more tailored pieces.

2. Details. You need extra interest to keep yourself from looking like an amorphous blob. Shoes, accessories, grooming and other accompaniments are crucial – they really can make or break the look.

I’m very happy that outsized pieces are coming back into style, because for ages I’ve been trying to source a looser-fitting winter coat that I can layer over knits and tailored jackets. I’d be perfectly willing to invest in a gents tweed coat if I could find the right one.

Anyway, for a great example of how to look cool in a coat several sized too big, check out Tina Chow in her shiny black trench from YSL menswear

Alexander Wang first came on my radar when I read an article about fashion week in the Wall Street Journal, in which the writer wrote this:

“Mr. Wang’s style isn’t for everybody, but maybe that’s the point. The designer, who threw a raucous party Saturday night in the middle of a parking lot, has a cult following among downtown women who are already so cool that they look good in spite of, not because of, his often unflattering silhouettes.”

Once I read about that kind of style philosophy–to look good despite your clothes, not because of them–I knew that was a challenge I wanted to undertake. I can’t really afford AW’s clothes, but I love to admire them, because they are often unflattering but at the same time beautiful and unique. I try to incorporate that concept into my style every once in a while, with harem pants, grandpa sweaters, and oversized blouses.

If there is one fact that had made the biggest impact on my dressing since finding YLF it’s been learning about proper fit. A slight tweak in sleeve length or hemline or pant length has really made a difference in my outfits and my confidence in wearing them. When I see oversized, slouchy non fitting items I never think the outfit looks “good.” Yes I may think it looks “creative” or “artistic” but for me it’s not a long term durable look. I always wonder how the outfit would look with a proper fit instead.

Lisa, your comment really resonated with me. I wonder exactly the same thing!