Griffin - I got it and it was very thoughtful, sage advice. We've all been there (I'm there with the BR dress now, lol!) I'm going to take your advice and pull out what makes me feel invincible

@Lisa - I've given up on a lot of the items you mentioned too. The key for me was realising that for every person who looks fabulous in the 'essentials' you mentioned, there's another who can't quite carry it off. For example, for all the style bloggers who make white shirts look so good, I've seen others who look rumpled or starched or just ill at ease in theirs. I know that's how I would look in a white shirt because it just doesn't feel very 'me'. But I know I can carry a draped pashmina with the best of them- so that's my essential

Thinking about Trench Coats - they are very climate and lifestyle specific.

If I commuted on public transport or walked to work in a professional setting they would work really well for me for autumn and spring, and maybe on some winter days. My climate with a lot of rain, no snow, and a temperate climate would suit them well... With an umbrella I would feel quite put together.

But.... I do not work in a professional office, nor do I walk to work. I either work from home or from an office that I drive to (15km away- no public transport). Driving in a car a trench makes less sense... If I am walking in the rain I am usually wearing a proper raincoat with a hood. Our rain is torrential often - not misty. And if it is too cold it gets a bit bulky layering underneath.

To me trench coats seem very English - perfect for the misty rain when catching the train to work in London or other large cities.

I do like the look of an open trench over jeans and a tee or shirt.... but have never really pursued it.

Jussie, that's right -- the black is just too intense. Though I won't completely give up on it...I suspect there's always one that could work. It would need to be more subdued in hardware. And that blush jacket (which I got from another Fabber) was lovely in that respect -- no epaulettes.

Sal, exactly on trenches....perfect for urban temperate climates. I wear mine in spring and fall here, and every blessed day when I travel to Vancouver!

Put my denim shirts in Finds. The western one is actually chambray (soft, but a dark wash) and the detailing can be great or not, depending on my needs. The BR one is longer, simpler, and crisper -- needs ironing. I think the reason these work for me is that dark denim is pretty much my best neutral and colour -- I mean for flattery reasons. So wearing blue up top is a no-brainer. The only problem is if the bottoms are also denim -- but since it is easy for me to wear different coloured jeans, I'm okay with this. Also, being square shouldered and small busted, shirts are an easy fit.

If my legs looked like yours, I'd be in skirted leggings all the time.

I quit trying to make those must haves work for me years ago because I got tired of the endless search to figure them out. I guess they just weren't me, and if none of these pieces have worked for you ever, then that's ok

I think the pieces you listed, although in a lot of must-have lists, are actually very difficult to get right due to variations in body shape and inidividual style. In most of these cases, it would seem that a person is looking for items that are body skimming but not tight--and it can be difficult to find that proper balance. Add in stylistic variations, and it's really tough.

I've tried denim shirts and had problems with them feeling bulky or too masculine. I almost kept the J. Crew one Suz linked to, but I felt that the pockets were too large and prominent on my small bust, so I returned it to the store.

Denim jackets are tricky because there is a lot going on. I feel like overall, denim jackets are kind of masculine, so I need enough feminine detailing to make such a jacket feel like "me." You have to be particular about length, which can fight with hemlines on your shirt and the waistband on your pants and the width of your hips (I run into the last element a lot...jackets just hit me in a weird spot). I really don't care for denim jackets in general and have one only because sometimes a denim jacket works where nothing else will.

White button-downs I find challenging because I like to be able to tuck them, but that means I have to be careful about how much fabric is in the waist, or I look sloppy. Also, if the collar is too stiff, it stands up in a weird way that makes your torso look boxy. Here you have to walk the fine line between crisp enough to not lose its shape and relaxed enough that it doesn't look uber-professional. And then you have to deal with the style elements: I don't like to look preppy, so I have to be sure to find shirts that don't read "preppy" to me.

Trench coats always make me look wide. I've decided that I need a single-breasted one and not a double-breasted one; it's the double-breasted design that is the problem. But I"ll be darned if I can find a single-breasted trench!

My experience with bootcuts is that most of them look too "business-y" on me rather than cool or relaxed. So I have one pair, which still reads kind of business-y, at least from the front, and I will not purchase another unless it is not so professional looking.

You're definitely not alone! I had to laugh about gryffin's comments, particularly about the denim jacket. I went so far as to collect a bunch of them in finds, and then realized that I would never wear one. I don't like wearing denim to work. Weekends, I'm often wearing jeans or a denim skirt, but denim+denim just looks odd to me. Nonetheless, for nearly a week, I was pretty convinced that I should add a denim jacket. Boot cuts have never appealed to me, and I haven't worn a denim shirt in 20+ years. Other items that are certainly essentials for others, but not likely to find a home in my closet are skinny jeans and white jeans.

I do wear white shirts, but from some of your other posts, I think the ways I wear them (to add crispness to outfits with longer cardigans or when I need to edge toward business formal, paired with black pencil skirt and fitted herringbone jacket) might not fit with your general style direction.

I am looking for a trench, and Sal nailed it, as to why I think it will work for me. I live in the mid-Atlantic part of the US, and I take the train/walk to work. I have 3 trenches on order- hoping one will work.

I completely relate to this entire thread! In particular the trench coat is my nemesis. The last thing I need is a bulky belt around the middle. A straight, beltless trench like style is great on me, but that is not really the thing is it? I have given up on shirts unless they are silk or silk like and flow back. Stiff shirts make a cube from the biggest points. And so on.

Rather than purge them all, why not pick ONE of each of these items - the best from your collection - and donate the rest? I have just one of each of the items you list, with the exception of the jean jacket (I have 3). Most of my garments are 3-5 years old. I do not consider them essentials (thus the reason for only 1 of each) but sometimes they are just the thing for a given occaision and I'm glad I have them in my closet.

Along the same lines is the leather moto, the LBD, the flannel shirt, the mariner-T, the black pump, the white sneaker, etc.

I found myself nodding along as I read each of your categories!

1. denim shirts - I always admire these on other people, but when I put one on, I feel like I look like my elementary school lunchlady from the 1970s who looked like she had been brought over from her former job of running a women's prison in Siberia, and was now put in charge of riding shotgun on 700 elementary schoolkids. Dumpy, frumpy, and the subject of mocking laughter when my back is turned.

Okay, I'm exaggerating. But in order for a denim shirt to properly fit my bustline, it means the sleeves are too long, the shoulders are too wide, and from the ribcage down, I'm going to be swimming in fabric.

2. denim jackets - when I wear a denim jacket, I notice that people see me as 'approachable' and a lot more likely to come strike up a conversation. I even have liked how some of them look on me. But the fabric is very uncomfortable to me. Even stretch denim. I just don't love how a denim jacket feels on my arms and shoulders. I feel heavy and suffocated.

3. trench coats - You said, "I feel like I'm in a costume". Reading this got me thinking... ironically, that's the one trench coat I've kept - a black patent leather one that has a spygirl vibe.

I think that most trench coats feel wishy-washy to me. Like they don't 'commit' to whatever vague idea is floating around in the back of my head, of how they're supposed to look on me, and make me feel.

Maybe you need to just commit, and grab a costume-y trenchcoat.

4. white shirts - I generally seem to have the same type of fit issues that I do with the denim shirts. I definitely have the same problems trying to keep it spotless.

5. full length boot cuts or flared jeans- these are inevitably a 'nope' for me, although I had some Christie Fit bootcut slacks by Victoria's Secret 10+ years ago (when they were making amazing outwear and streetwear) that I loved - and then my freaking dry-cleaner shrank them. I bought a replacement pair, and wore them in Chicago. That's when I realized... even if your ride drops you off right in front of your destination, those flare pants pick up everything in their path.

6. Booties/Shoe-ties - In theory, this should be an ideal wardrobe addition for me, but I always feel like my legs look like scrawny flower stems in big pots.

And those bootie things that have open toes, for whatever reason, make me think of dog's paws, when the owners paint their toenails.

Lisa, only one item on your list as a regular part of my wardrobe, and another which is an occasional player.

Demin shirts, denim jackets, trench coats and boot cut/flared jeans have no place in my wardrobe lol.

After years of on and of trying to make them work, I realised none of these items actually reflect my style preferences, I don't like how I look in them, and I have given myself permission to not bother with them.

I have to admit that I do have a soft draped trench and that works well for me, but a traditional trench (say the classic Burberry) just looks wrong on me. And the one I have is worn infrequently

I do have a love of the white shirt because they can look quite cool and edgy, but mine are all for the purpose of layering. I never wear a white shirt on it's own. I recognise it's not my best look in terms of figure flattery but that is not so important to me.

I am going for the "trying to hard to make things that are just not me, work?" in your multiple choice answers.

However, in the event that you really want to make one or more of these work, I would ask this question. "How would I wear it"? (as in you Lisa)

I think we can be crippled by how we see models and others wearing items and feel that is how we should wear said item and that is how it should look. Allow your creativity to flow.

For example, I know that I don't like the look or feel of a structured trench, but I can wear a soft fabric-ed, unstructured version.. it's more in line with overall style aesthetic.

The items you mention are all pretty mainstream items (and that's not a negative by the way, just an observation) and yet I wouldn't describe your style as mainstream. Does every woman with a strong signature style have those items in her wardrobe? Bet she doesn't.:)

Apologies if I have gone off on a tangent. xxx

OK time to weigh in ( pun half intended). Most of these I have *never* owned, in my whole life.
1. Denim shirts, never. Not a fan of "button-down" shirts much for a few decades and feel they are too plain and too masculine.
2. Denim jackets, never. Same feelings as above. Too plain, too masculine, too heavy, don't want to do double denim. If I'm that casual it might be jeans on the bottom. Owned one denim skirt when I was 15 and never denim shorts. Only jeans.
3. Trench coats, never owned one. In decades past they looked too boring ( beige) and now would have to be such a swing shape they prob wouldn't be a trench anymore. And I'm still not a fan of beige.
4. White shirts. Not for decades. Too plain, no detail, too likely to get crumpled, too stiff. I have white tops. Last bought a collared shirt in a pale colour aged 24 and it was cream silk with a placket/cowl neck and not a full button-down.
5. Bootcuts. Got rid of my last black pair from maybe 2011 last year as they looked dated to me. Got rid of my bootcut jeans from 2007 this year as last worn 2015, felt dated and were tight round the middle.
I feel no guilt at not liking these things. Even though I was a pear and bootcuts are supposed to "balance" me, I came of age in the 80s when skinnier styles were in, then was a young Mum in the 90s in leggings. I'm much happier in my ponte pants and some straight legged jeans . I'm sorry to hear that you have bought so many of these things if they've never seemed right. Lesson learned now?

Many years ago I stumbled upon these "Must have" lists and I thought I had found the solution to my problems. But it was not so. After many shopping mistakes and wardrobe orphans I finally decided to send to hell all those suggestions about white shirts, LBDs, high heel pumps and black jackets. Some things are just not for me and will never make me feel happy, no matter how well I can look in them.

I think we have to accept that certain things are just not "us" and probably never will be. Like you, I have never been able to find a trench coat that works for me - especially those in the traditional stone/tan/khaki colours, so now I simply let them pass me by and choose another style. Likewise, the white shirt - or any colour shirt for that matter. While they look wonderful on some, on me they just look too masculine and formal, so I leave them on the rack
.
Sometimes I laugh at myself for taking so long to define my best - and worst - styles, but it definitely gets easier with age! .

lisa,

It's really a different strokes for different folks kinda thing. Like Suz and Sterling, I can't do tunics. I look ridiculous in them. I finally just let go of the notion that I would ever wear one and try not to look at them anymore because I really do like them on other people. If I look, I'll try. Same with booties and almost all boots (except OTK and only with mini skirts) but I keep buying them. I've decided to stop and put a note in my shopping notebook to remind me how ridiculous I look in them.

Oddly enough, I only ever wear denim shirts in the summer and it's freakin' hot here (Georgia). I use them as a topper. They look alright with white shorts, a cami, and sandals. Otherwise, they just hang in my closet. I only use them as a topper because I haven't found the right thing yet. When I do, I'll probably keep one for going to the Walmart and let the rest go. I feel like they look country (corny country - not cool country) and that's not me. I feel the same way about embroidery but I've only seen one or two things I would wear and I hesitated so long, they sold out. Along the same vein, I don't get denim dresses. That's one thing that I consider a staple that I keep buying and never wear.

I just started getting into trench coats. I finally found the right one and figured out how to wear it. Again, I live in a different climate so a lightweight coat is more appropriate for me.

White shirts - I have one. Never wear it, either. I'm assuming you mean button downs, btw. I do wear white turtlenecks and t-shirts.

Flare jeans. I love 'em. They look good on me but it's hard to find them to fit and I won't alter them unless they only need a little off. I dunno what's going on with inseams but here lately it's been hard to find anything less than 32 inches - and that's in a short!! I was looking at one pair of pants last night and the regular (not tall) inseam was 37 inches!!! Where the heck are they getting these fit models? Themyscira? o_O

Again, different climate. I only have to worry about snow one or two days a year and Georgia usually shuts down for those days.

Edited to add...

Denim jacket - I just pared down to my favorite. I only wear it in the spring/summer with a t-shirt dress and my white converse. I haven't been able to make it work well with jeans (denim on denim is a trend I wasn't fond of when it came around the first time) and I have so many nice jackets I prefer to wear with pants that it never gets any play.

I have almost learned not to buy these things... however, I succumbed last year and tried the denim jacket again - band jacket style. Besides the weather never being right for it, it is strangely too casual for my decidedly casual self.

I'm pretty sure this is why Angie encourages people to define their own essentials; it's so easy to get led astray by those "Every Woman Must Own" lists, or just by the amazing outfits other fabbers put together. Like others, I have very few of these items in my closet, although I can imagine finding "my" version of most of them if I felt like hunting.

1. I don't own denim shirts, but do have two printed chambray shirts. They do not have chest pockets, and they are quite tailored in fit. If they were sloppy, long, boxy, or had big pockets on the chest, they would not get worn (ask me how I know...).

2. I didn't have a denim jacket, or a desire for one, until last summer. I added a white one for the exact scenario you describe: a structured casual summer topper for jersey and knit dresses. Like Suz, I wore it until about the end of September and won't take it out until spring. It took a couple months of try-ons to settle on the Kut version; everything else I tried was too boxy, too stiff, too costume-y.

3. Never owned a trench coat. Not weather-proof enough for the kind of rain we get in the northeast, so they've always seemed a little frivolous to me. I do have "city rain coat" on my long-term wish list, but it probably won't be a classic belted trench. More like a waxed cotton Barbour coat or something, and definitely black or navy or olive, not beige or taupe.

4. I've tried a lot of white shirts and kept none of them, even though technically many of them fit. I like my shirts to be able to stand alone, and a solid white shirt just feels like too large a swath of white on me. I would have to treat it as a layering piece, like Deborah does, but that does limit its supposed "versatility" IMO. I do have "blue oxford" on my list for this spring/summer. Due to an influx of printed pants, I finally have a need for some solid-coloured shirts, but I don't think crisp white is the right direction.

5. Bootcut jeans. I retired my last pair last year. Vintage Red Engine -- I wore them into the ground. Really great denim, and cut just perfectly for me -- length, rise, everything. They were a unicorn and I miss them, but they didn't leave a gaping hole in my wardrobe. I came of age during the flare/bootcut resurgence of the late 90s/early 00s, so I had a stink-eye for any sort of tapered pants for the longest time. I have one pair of flared pants now, mainly because they are fully lined wool trousers in a plaid that I really love. I would like to find a new pair of sailor pants, which would be a full-length flare or wide-leg, but it's not a silhouette I'll go out of my way for. I have proportionately large calves, so jeans were always an easy fit for me back in the heyday of bootcuts, and it has gotten harder now that companies are designing legs that are so skinny and SO tapered.

6. Hah, I see you've added booties/shoeties to the list! This one is hard for me too. I find that the wrong height for booties (or hi top sneakers for that matter) gives my legs a bulgy look, and cuts into the front of my ankle when I walk. One of those instances where poor comfort and poor flattery align.

My own personal demon has been skinny jeans. I absolutely cannot achieve the relaxed-skinny look because my legs, especially my calves, are just too big relative to the rest of me. Every fall I get it into my head that I want to be able to wear big cozy flannels and long sweaters over skinny jeans, but then I do some try-on's and remember that this look is the exact opposite of what works for me, despite the fact that everyone else seems to wear it. Like Suz, I've also had to swear off tunics for the most part. I also have to exercise a lot of restraint with tall boots; because I don't have any skinnies to tuck into them, they end up being for use with skirts/dresses only, and, again, not as versatile as they are in other people's wardrobes.

Like others have said, I could see you in drapier white and denim blouses, rather than shirts. And maybe a black or olive anorak instead of a trench. I don't really see any of these as essential to your style -- it is, as you say, a question of how hard you want to work at making something work for you, finding the right version, etc.

Lisa, you have started a great thread and the comments are truly wonderful. Gryffin's advice and Suz's quote make YLF more than just a place where we talk about fashion.

Of the items on your list these are the one's that don't work for me:
Denim shirts, love them on others, feel like a fraud on me.
Denim jacket - I have one and only wear it over soft casual summer dresses when it cools down at night time. I could use a wrap instead, and don't really need it but keep the one denim jacket I own.
I once had a pair of flares but to make them flattering I wore them with 3 inch heels and then because that was the length they were hemmed to, I found the shoes too uncomfortable and did not wear either shoes or flares. I much prefer other jean styles.

Of the so-called classics, I have tried and failed - the only success was the black leather jacket - as I found the "right one" for me:
Bomber jackets are terrible on me. As a pear shape I need waist definition (because that is the good bit on me). Bomber jackets bypass the waist and make be look much bigger than I am. I can wear a cropped bomber jacket but not a classic longer line bomber.
Tunics - unless they have a tapered shape, tunics stop at the hips which is my widest point and don't do me any favours.
Black moto jacket - too hard edge for me. I have a beloved black leather jacket, but it is a soft leather, has waist definition and a slight peplum effect at the back. Not a stock standard moto jacket and a much better style on me.
Turtle neck knits - I don't like the feel of these around my neck, crew and v-neck knits are much better on me.
Chunky knit sweaters - too much volume and make me look big. Last time I wore one, was asked if I was pregnant (and I was not), so not prepared to try this again in a hurry. Although, I often pin stunning chunky knits on pin-interest... obviously a great look on others, just not for me.

This thread has confirmed to me that the "Classic items you must own" lists are nothing more than guides on what may be useful. I give myself permission to thoroughly reject any of these on the basis that they simply don't work for me at least in a general sense unless I find the rare specimen that does work.

LisaP, The items on your list don't work for me either. I'm fine with that.

Instead of a traditional trench, I am loving the version that Elizabeth Suzann designed. I have this in black cotton canvas. Easy for layering tops or sweaters with sleeves underneath.

Didn't we both buy this great tan wool Eileen Fisher jacket a few years back? It is still one of my favorite and most worn jackets in the fall and winter.

My steer clear of list:
 Garments that have too much structure
 Sleeves that are too tight, especially in an outerwear garment
 Anything fussy
 Turtlenecks...cause hot flashes LOL
 Pants that are too low...midrise is too low for me now too...always    pulling up

Edited to add a photo from a while ago...this is my version of a jean jacket. Eileen Fisher, easy collar, soft cotton fabric, and sleeves roomy enough for layering.

Oh, you know what else I absolutely can't make work for me? Those chino shorts that J Crew, Gap, etc always sell in 10 different lengths and 100 different colours. Nothing makes me feel more like a bad caricature of a MOTG than wearing chino shorts.

I love this list! I have the same issue with all of these. I buy them, try them, and then they sit in my closet. I love white, but "tops" rather than "shirts". I have one denim jacket I wear occasionally in a faded black, one pair of denim bootcuts (they have to have skinny thighs and then they make me feel like I have long legs). I have a chambray shirt that would be good for layering except it has doman-type sleeves so doesn't work under a lot of items. I've never had a trench coat, they just aren't me. I wear warmer coats most of the time and when I need a lighter coat it has to have a hood. Plus they just don't look good on me.

I agree with Gryffin, I see some items here and they are so pretty and look so nice that I want one, but have to step back and figure out if they actually work for me. Sometimes I have to own an item before I figure it out.

I think it’s just that everything isn’t for everyone. I’m learning that more and more and feeling more comfortable passing on trends and even all those lists of basics that everyone should own.

I’m having trouble with leather jackets. Everyone looks so great in them but I just am not feeling it. I did sell a few that didn’t fit well but I have a few more that I love to look at on the hanger but just don’t feel right when I try to wear them. It just doesn’t compute with me because I wore leather jackets all the time and now I just feel odd in them.

Denim Shirts: DITTO! Actually my all-time favorite is from The Gap in the 90’s and it has snaps. I wore it to death, even under a suit when my company went business casual. I could never part with it so it was demoted to my gardening capsule with cross-over to my dog grooming capsule. I still wear it. I’ve often wondered if my problem wearing a denim shirt now is because I’ve been there and done that.

Denim Jackets: Another DITTO! And similar situation as denim shirts. I wore the heck out of my denim jackets and then I stopped. I finally sold a couple last year and saved my favorites but I really never wear them. I do carry them around as a topper in the summer because I run cold and they don’t get all wrinkly being thrown around.

Trench Coats: Totally my jam. I have a few in a variety of styles and I wear them, totally love them. Wish the weather allowed me to wear them more frequently. The belt is fiddly but I power through that and just wear them. But it’s difficult to get a good fit. The two that get the most wear from my stash are the least traditional; a leopard print with light removable lining and black with leather sleeves.

White Shirts: LOVE! Wore to death in the 90’s under suits. I have one remaining in my closet. But I don’t wear it. I have longer hair that gets tangled in the collar so there is that and I always just feel like it’s a high maintenance per wear item. Every time I consider wearing it (or any of my button up collared shirts for that matter) I opt for a knit instead because it’s just more comfortable and more suited to my lifestyle.

Full Length Boot Cuts or Flares: I have two pair of beloved Hidden Hills in my closet that I wear maybe once per year. These are the absolute most flattering and comfortable jeans I have ever owned. I don’t think I will ever part with them. I don’t wear them because the weather conditions need to be perfect, the whole PPL/shoe thing and currently mine are tailored for high heels and I have rare opportunities to wear heels. When I do wear them it’s summer and usually with wedges. I also have my own vintage pair of jeans I let them hems down to give them some pizzaz and a pair of white that I attempted to wear but before I even got out of my garage my knee rubbed on the car tire and made a huge black mark. I had to run in and change. Overall these are all just too exhausting to wear.

I think a two-season 3/4 length coat is a really good thing to have in your closet. Not sure you really need a trench per se, but maybe something dressier than an anorak.

The rest of these things are more about style, and I don’t think you need them at all.

Laughing at myself for feeling the same way about many of these items. I still have 2 denim jackets - one white, worn twice, one dark denim, worn enough times in years past to justify passing it on but for some reason I keep it still. I should pass it on.

I have two denim shirts that rarely get worn. I love the faded one but it's really a bit large so I mostly use it as a swim cover up. The darker one feels just a bit too stiff to wear very often. I never found my "perfect" denim and decided to stop looking.

White shirts for me have to be a bit "dirty" already - meaning soft and non-iron, not pure white and definitely not ivory (yellow tone I mean, which doesn't work for me at all). I prefer a slightly off gray-white and only own 2 one flannel, one short sleeved.

I think Angie hit it on the head for me with several of the items having "a masculine vibe and stiffness to them."

Trench coat - well, it's never cold enough here in spring for me to wear one. I finally passed on my black London Fog after many years of not wearing it.

I don't have most of these items either so you're not alone. My style is fairly classic so it seems like they would work for me but they don't.

• I've never liked denim jackets - too stiff.
• I have one denim shirt and I rarely wear it. It's too stiff even though it's a really soft denim.
• I have a couple pairs of boot cuts but I don't wear them very often. I don't have weather issues - it's pretty much always dry here - it's getting the exact right heel height that always causes problems. I have LOTS of shoes and being stuck wearing only a few pairs always bugs me.
• I've never worn a trench coat and I've never been interested in finding one. I've never actually seen anyone wear one in real life. It must be my geographical location. I work in a professional environment so there's plenty of opportunity for people to wear one.
• I have one white shirt that I'm debating getting rid of. I can't ever seem to get them quite right - they're too stiff or too soft (current problem), too short, too tight, too sheer, etc.

WELL. This has been very instructive and interesting. I feel like I've been released from some fashion obligation and will be ditching my denim jackets, trench coat, and denim shirts asap. The one thing that stood out from among so many comments was the masculine vibe presented by most of these pieces - and it makes me wonder why they are on so many "you really should have" lists when that is the case. I do not have that classic, gamine, minimal look to me, which is where these kinds of clothes really shine. Again, very interesting.

It's also interesting to read more than one comment about how tunics and leather jackets are 'no go's ' for many of you. I LOVE leather jackets, but have winnowed my collection down to two moto style ones both in black. The collarless, zip front ones from the 90's -00's - out they go. And although classic motos are most definitely masculine, they have an edge to them that a denim jacket or shirt or trench decidedly does NOT have. I always wear my leather jackets with a very feminine silk top underneath too. Tunics have been mentioned a few times, and that I find curious. I live in them : they cover my butt and front, and are so easy to move in. Weekend staple. Anyways - thank you ALL for stepping in with your comments !

LaP - I'm laughing at the GAP chino shorts. I love them. I feel that way (caricature of the MOTG) in denim jackets, I just realized. I know exactly what you mean, however, but shorts are tough to find, and I know I can always find a pair there. I guess I'm old enough to a) not care and b) be way past the MOTG stage now anyways . Speaking of shorts - where are the good ones ?? And , no, I don't have boots/booties on my list . Not sure what you mean. I own about 800 pair of booties and clearly have no trouble wearing those ! Culling those today in fact.

Lisa p, told you, you were in good company! I dress women for a living, and there are many, many common themes. I bet this was quite the exhilarating and overwhelming thread to read and absorb. But satisfying and validating too. All good.

Off you go to pass on ALL those items that don't work. My toes are ticked thinking about it....

*rubs hands together with glee*

I kinda like the chino shorts too -- I just have to make sure I edge up the footwear with them a little bit. But I do have a little sporty/preppy shadow style.

I'm glad you feel liberated from the tyranny of the denim jacket and shirt!

Oh, hah, it was LBD's list that included booties -- ended up reading halfway into the thread without realizing! Clearly you have touched a nerve with your list of Not-My-Essentials.

I am slowly reaching the conclusion that there are no good shorts and trying to fully embrace the concept of summer skirts and dresses. I have a bunch of gear shorts, a couple pairs of cut-offs, and that's it. I used to wear chino shorts all the time; it's wearing them while accompanied by a preschooler that makes me feel a little...hokey. I should probably feel that way about other preppy things too, like breton tops, but I'm never ever giving up my stripes.

For me, Lisa, the problem with tunics is proportion. They cut me in half and make me look like a block on stubby cut-off columns. Show how short my legs are no matter how I try to disguise. Make my legs look chunky instead of svelte. Well, my legs are sort of chunky, relative to the rest of me, in fact, and mostly, I'm okay with that. But this is less than JFE. If I were short but with relatively longer legs, tunics could work brilliantly.

I'm tempted by them because with my strong shoulder line, they seem like they could work, at least with the right footwear, and I want them to work so badly.

The only kind that do work are the asymmetrical ones. Those are sort of magical.

LaPed, I struggle with shorts, too. I do wear them, though, for reasons of practicality. But they're rarely my choice for flattery. It has to do, again -- with proportion and leg shape vs. overall shape, I suspect. And being short...wearing shorts can make one feel childish.