I bought a similar shirt at Target recently (certainly not haute couture!) I would wear it (or the upscale version) with skinny jeans and booties and maybe a black cropped jacket. But I also like the belted look with leggings and boots. I’m short, so it would probably be dress length for me.

I love the idea of the long flowing painter’s shirt, its so free and effortless yet chic. I would wear it belted with leggings and heels or with skinny jeans and sleek flats. I also think this would look amazing with the obi or corset belts that are turning up everywhere this season.

I would wear it!!!! Totally! Actually I saw these worn as dresses with sweaters and heels and I really liked the look, so much so that I saved the images as ideas. I even stole a Nordie shirt from my hubby to see if it would work but it was too short. I just didn’t realize these shirts are called painter shirts.

I’m going to be honest, wearing this would be a GIANT leap into new territory for me, but I’m intentionally trying new things with YLF’s encouragement! Since moving to a downtown area and being influenced by local street fashion, I would wear it with my beige skinnies and heels or booties for a night out with friends. It does feel a little reminiscent of oversized shirts I wore over stirrup tights when I was in grade school, but I think it can be glammed up so I don’t feel like a little kid.

Angie, could an open waistcoat work over this shirt? Or would that look odd to have a teeny waistcoat over so much volume? It seems to me like the only layering you could do without taking away the focus from the shirt is to wear a coat or trench if weather was cold.

This is definitely my style. I like loose comfy things. I would wear it with walking shorts and a vest or depending on where it hits me (I am 5′ 2″) , just by itself.

Do you think I could wear it pregnant? I think I would– it looks so comfy. I would wear it with skinnies or leggings. I would wear it with my grey slouchy over the knee boots and my MK wide chain belt (at the waist once baby is born).

I wore this look a lot unbelted back in…was it the 80’s? I would wear it again but belted with narrow jeans or pants, a cami, and pearls. I especially like the idea of belting it high. It would be a new take on my uniform of buttondown shirts over a cami/tank, belted, and jeans.

I would wear it like in the third picture. Low slung belts are my friend!

I would wear it! Actually, this is reminiscent of my “chef” blouse, which I absolutely love.

I love this! I’ve been experimenting with volume on top lately.
I would wear it with my new grey skinnies, peeptoe booties, and either a waistcoat or funky belt.

Wow, what an interesting item. It does look like the oversized shirts of the 80’s. I like the idea of wearing it with a waistcoat over skinnies or leggings. Sounds like a fun outfit! I think it would be a nice change for my MOTG uniform.

I would wear it!

I just got a pair of red skinnies with a bit of a sheen to them, and I wanted to wear a white blouse over it. Mine isn’t giving me exactly the look I want (it’s fitted and not quite this long), but this shirt would be perfect!

I love skinnies and boots, and I have skinnies in many colors, so a shirt like this would be great to wear with all my colored skinnies. Or with my oatmeal or black skinnies for a neutral looks, or with colored boots. I would also play around with different color belts or scarves-as-belts.

I could probably also wear it as a dress with colored tights or leggings under it. Maybe with some short shorts that really wouldn’t be visible. This shirt would get a work out in my closet. Maybe I should look at buying one soon…

I *think* I like this… I do love volume but often worry about being overwhelmed by, you know, so much of if! I’d be thrilled to give it a shot, though! I would wear it with my black skinnies, black lace-up booties and a waist-cinching belt. I’d probably throw on a bold necklace, too

Ooh, I would wear it over faded black skinnies with black gladiators and hair back in a bun. Or as a mini-dress.

I would wear it. I like your suggestion of belting it at my natural waistline and of course, it would only look good with the skinny jeans & heels. I don’t know what kind of jacket would look good over it – just have to try different ones.

Helen Weber

Pssst. Some of you are forgetting to say: “I would wear it…..” in your comment. We will only put those comments in the random generator!

I would wear it both unbelted, and belted, with skinnies, or leggings and tall boots. If belted, then the belt would definitely be on the natural waist, not on the hips like on the model. It is a pretty cool item, I love the relaxed vibe.

love this! it’s pretty outside my comfort zone, but i would wear it with skinnies, funky ankle boots, and perhaps a belt — though i’m thinking an open vest might be pretty cool too, maybe with a pretty scarf… oooooo, so many possibilities!

I would wear it! With heels, pearls and a corsage, or denim leggings and boots or a long knitted vest and slouchy boots.

What a fantastic opportunity Angie

Thank you YLF

Oh yes. I would wear it. Since I’m short, it’d have to belted, with a big Elizabeth & James sweater. Thanks for the giveaway!

I would wear it, sure.Just got into skinny jeans and these are begging to be thrown over a nice dark pair.Sign me up!

Oh! How pretty! I would wear it with dark denim skinnies tucked into equastrian boots and belted at the waist

I would wear it!! I think it’s so cute with a low-slung belt and skinnies!! Swell giveaway, thank you!!

Awesome sihirt, love it! Glad I checked your blog this morning I would mostly wear this without a belt, and would give it a try with a belt as well.

This would be so fun to style. I think I would wear it with a big chunky bib necklace under the shirt with a simple slightly loose belt at the waist. Definitely with skinny jeans or leggings and my black booties with the big silver buckle. This would be so fun!

I would wear it with skinny jeans, booties and a really chunky necklace. If I’m not lucky enough to win, I’m going to put this shirt on my must-have list for fall.

I would wear it with skinnies and belted. I’ve been looking to try this new trend.

Now this is definitely something I would wear: with jeans or leggings-totally great for campus, running around. If I could wear high heels, it would really be great for going out in the evening. I could also put a long (but shorter than the shirt) loose sweater or cardigan on it for teaching class, with my boots. This is a versatile shirt, and worth the investment. I had a similar one, and it’s finally worn out after eleven years!

I like the look on the far right. I’m always trying to find the right look for one of those huge chunky belts and often come up dry. I would wear it!

Hi Angie!

This is a cool giveaway and I would wear it! To me it looks stylish AND comfortable at the same time.

Debbie

Great shirt! I would wear it lots of ways, I think. Definitely with skinnies and flats. Belted over a pencil skirt with tall boots.

I would wear it!! Probably like the third photo…

I think this is a great look, especially as posted in the 3rd picture with the belt. If you have longer legs, added with a pair of heels or boots, this definitely could be a fun look to wear and add accessories to. I would wear it.

Wow! It’s going to be something new to me but I would wear it! I am thinking of wearing it with leggings with boots or flats, with a waist belt and maybe with skinny too. I’ll also be trying to

Yes, I would wear it. I’ve worn this look for years, starting with a linen jeweler’s smock that I bought in a workwear shop in Paris. Slim trousers or a long, skinny skirt look good below.

This is a throwback to my favorite 80’s look and most definitely, I would wear it!

I would wear it with skinney jeans and heeled boots. I think it could look quite fashionable.

I would wear it if you told me I could get away with it!

I would def. wear this shirt if I was fortunate enough to win.

I would wear it with skinny jeans and boots.. big over small sillhouette..

I would wear it!

This is a great casual look – I love the crisp and clean feeling it has. I would wear this in a heart beat. A fun basic which can handle many different accessories.

Very interesting responses.

Red head and Joy, this item absolutely reminds me of the tailed shirts we wore with stirrup pants or tapered jeans in the 80’s. Only it was with gigantic shoulder pads back then. This is a great improvement. I’m all for the look of the painters shirt. Very fab.

I would wear it. It’s such a fun look that reminds me of the late 80’s early 90’s.

I would wear it! Thanks for the reminder, Angie

i would totally wear it! definitely with skinny jeans and boots/heels. i’d be wayyy too comfortable if i paired it with leggings…i love how it looks so effortless and chic!

I would wear it! Especially since I pregnant at the moment. I too would belt it a bit higher, which coincides nicely with the top of my baby bump.

I adore this look. I paint as a hobby, and I wear my husband’s old button-down shirts as smocks. The are comfortable, fun and I feel rather “with it” when I wear them instead of aprons. So…..I would wear it when I’m not painting!!! I would wear it with skinny jeans, leggings and a fun, flirty, ankle-length skirt with a wide, fabulous hip-hugging belt. I’d also wear the collar flipped up. It’s a great look.

I would wear it! I love the look of white shirts and denim, it would prompt me to actually get a pair of skinny jeans (on my list). I’d try it both ways, but think I’d prefer it belted.

I would wear it belted with skinnies and slouchy boots. I love the belted look!

I would wear it! With leggings, or over skinnies and probably belted. I think it would look nice with a scarf tucked in the collar.

We are going on a 7 day cruise in October. “I would wear” it as a cover up to go the pool and beach. Also I would wear it for lounging at home with leggings.

this would look great with leggings, a slouchy bag, and my short purple ankle boots! great giveaway!

FUN! I would wear it with some black leggings and my Frye Engineer boots. And be comfy and delighted.

Love the look. I would wear it…probably as a mini-dress with black ankle-length leggings (is that that same as what you call skinnies?) and black platform heels and a low-slung wide black belt.

i would wear it with black skinnies but the shirt buttons would be opened from the top to the waist, to elongate the line, with a wide red belt higher on the smallest part of the waist. Under it would be a dark gray tank top and my black statement necklace. With cage high heels maybe in saddle toned leather.

I would wear it. Love this look! I think I’d like it belted with black skinnies and boots

I would wear it. This would be great with a French beret, belt, jeans and boots.

I would wear it with leggings, tall boots and a wide black belt at the waist.

Even before looking at the pictures, I was thinking that I would wear it with straight-leg jeans, a pair of wedge heels and lots of chunky accessories. For cooler weather, I could pair it with leggings, boots and a belt. I have no fear of surrending my waist line as it disappers bit by bit daily, as my little Peanut gets bigger.

Wearing this shirt would be a whole new adventure for me, but I would love to try it. I would wear it with a belt and leggings and flats (lab appropriate flats of course).

I would wear it for sure! With skinny jeans and my red heels. Thanks for hosting a giveaway!

I feel like I say this about a lot of items, but this would look dreadful on my hourglass frame. The only small part of my body is my waist; I have a large build otherwise. This top would make me look obese. I would like to be able to get away with looks like this, but I know they are not for me.

I would NOT wear it (just to be clear I”m not entering the contest.)

It seems like a style that would only look good on tall, very thin people. I’ve got the tall part but not the thin. It seems like every time oversized clothing comes back into style, big girls always jump on it because it “fits” but the truth is, these style don’t look good on big girls, IMO.

I would totally wear it with a jeweled belt (probably gold, I like white and gold), belted at the natural waist. I’d add chunky and complicated bracelets, since it’d be a little too much to have a necklace too. Then bike shorts! under it, and paired with a sweet wedge, something with flowers on it maybe. With heels and no pants, it’d definitely look too girl on the street.

You know, I would wear it, but I would definitely do it with the belt. I’m not quite brave enough to go free-flowing.

I love the flowy, romantic look of painters shirts. Being a big fan of volume on the top, I would wear it. Since I’m short, the shirt would have the look of a shirt dress on me. I’d wear it with leggings and boots and some bright necklaces and cuffs.

I would wear it with skinny jeans and a chunky heeled bootie or oxford shoe. I have the ponte knit skinny pants and I would certainly give those a whirl with this big white shirt. I grew up with the idea of women wearing their husbands shirts. Was it Doris Day who did this? Anyway I have worn a mans shirt many times with Levis and it always feels alluring for some reason. I would wear it and enjoy the loose comfort while feeling alluring. I would have to play around with hip slung belts too.
Having this much volume might be a good chance to weat a larger scale necklace too.

I would wear it with jeans a belt and chunky bracelet!

This would definitely get me out of my comfort zone with is what I want to do.

I would wear it to work with a waist-cinching belt, a skinny pencil skirt, and fierce heels.

I love it! I would totally wear it with my orange skinnies, tan crocodile peep toes and a low slung belt and a bunch of silver bracelets on one wrist.

I love this shirt! I would wear it belted low with a silver and faux turquoise belt and dark skinny jeans, with red ankle boots for a little contrast. I would load up on silver bangles and wear a chunky silver ring on my right index finger.

I used to wear this type of shirt all the time, in the 80s. Worn loose over stirrup pants or belted or with a sweater vest over (and my red beret). But I’m 5′0″ so the trick is to find one that is scaled down – I’m sure this one would be much too big for me. If you’ve got a petite version I will be glad to give it another whirl! In the 80s I used to find shirts in the boys’ section. A 12-year-old boy’s shirt is just about right for someone my size!

With that said, my hubby loves it when I wear his shirts to bed… this look reminds me of that.

I would wear this wonderful long shirt with a lacy camisole unbuttoned and a low slung belt…Of course my skinnys and booties would complete my very se-y look…Since I am tall 5′9″, I feel that I can handle the length of the shirt, and the look…which by the way, I already wear…

I would wear it with the new love I found because of YLF – skinny jeans!
(I never thought I would ever say that. I bought my first skinny jeans three weeks ago, and now I already own three!)

painters and poets sure dressed fine in days of yore, all those flowing romantic white shirts!
i would wear it! maybe it would even inspire my inner artiste!

I love it and I would wear it!

Being 5′11″, I’m comfortable with the scale and length of this shirt. I already envision wearing it loosely belted over leggings paired with the fantastic slate grey suede over the knee Calvin Kleins boots I just purchased.

I would wear it! I will be post-partum shortly and I love items like this… forgiving in the midsection, but structured in other areas and therefore ‘put together’. I’d add slim jeans, silver flats, and a belt while out. At home I’d skip the belt to enjoy the lack of restriction.

I would definitely wear this! I love the look of the third picture and how romantic this look can be with loose wavy locks.

I LOVE the look and would definately wear it!!! (I’d wear skinnies or maybe leggings and most likely belt it)
Please put me in your drawing.

There are so many ways I would wear this great shirt–the first being with a skinny black mid-calf skirt and ballet flats. I’m petite, so adding an art pin would be a simple way of accessorizing, but I wouldn’t count out a putting a loose pointing front man’s vest over it for cooler weather.

I would wear it! Love it with the skinny jeans.

Yes, I would wear it! I love it. I’d certainly wear it with leggings, as many have mentioned, and more than likely with skinnies, which I am just about persuaded to purchase thanks to you all. (Thanks! This is fun!)

I would so wear it! I’d wear leggings and some cute metallic flats with it or maybe a great pair of ankle boots, belted like in the 3rd pic so as to not look like I’m wearing a fly-away sail! Truthfully, I recently bought 2 pairs of leggings and I’m a little intimidated by them, I’d love the chance to try something new.

This would be a new look for me but I would wear it belted with skinny jeans or leggings or layered, unbelted, with jeans and boots! It offers great versatility.

Hm, somehow I pictured a poet shirt when you were talking about painter’s shirts, Angie. So I’m disappointed in the look. I’d wear a poet shirt, but I’m not this plain, long, boxy button-up. I guess that’s because I have to wear white button-ups to work every day.

I have always loved this style. I would wear it probably with leggings and a belt, but I also like this type of shirt over a long lean skirt.

I would wear this shirt with black leggings and a cropped black vest. I would add a long pendant-type necklace and add colorful suede knee boots.

I would totally wear this.

i love this!!! i would wear this just about anywhere! i’m both a student (grad school) and a teacher (drama)…i would wear it to either kind of school.

Oh! Very cool and comfortable looking. I would wear it with skinny jeans and boots (belted or unbelted) or with leggings and ballerina flats (I’m short–so I think it would come down pretty far on me.)

I would wear this with a chain belt over skinny jeans or as a bathing suit cover up on the beach. It’s totally chic! Many thanks for this opportunity.

I would wear it to work,it would be comfy and the hair would not stick to it.

I would wear it with a big necklace in black.. I love the shirt!!!

I have tons of shirt like this! It’s a staple for me. I would wear this as I would wear all my painter shirts. I’m an amateur painter, and these are great to wear on the weekend with leggings while working. Super comfortable and I feel that wearing this somehow gives me more validation as an artist all psychological. Most importantly, I feel great wearing it.

I would wear it in the house
I would wear it when walking my mouse
I would wear it with jeans
I would wear it with seams
I would wear it here and there
I would wear it anywhere

Can you tell who’s lately been reading Dr. Seuss books to their children?

Seriously though, I would definitely wear this shirt. I love this type of look when I can combine with tailored elements. I have a similar shirt that I wear with skinnies and with the jacket over it and really long, dangling earrings.

This looks like a great summer shirt. I would wear it at the beach to keep the sun off my skin as well as with skinny leg jeans. I can also see myself wearing it when going for a big meal so as to hide any self-conciousness regarding a bloated tummy!

What a versatile piece. I would wear it with just about everything in my closet right now. It is terrific.

Totally! I would wear this shirt! This shirt IS my style – I love with a belt, but wouldn’t you really want some leggings under this – or here is the opportunity for the skinny jeans – yes, yes, I would wear this!

This would be a huge step outside my comfort zone, but if “one size fits most” would fit me, I would wear it! I think it would be a great tummy-concealer on me. I would wear it with dark skinnies and bright accessories. I never wear white but this looks fun!

Oh, I would definitely wear it!! A crisp white shirt belted with dark denim skinny or boot cut jeans with heels or boots. Adorable. Very 80’s. I even have my hubby’s work shirt that is similar that I used as a pool coverup this summer. This would be the twin to it for everyday chic wear!!!

I’ll wear this shirt with a long chain necklace, tights and riding boots. but no belt. or belt it up, wear the shirt with a thin black tie and flats and tights. obviously i really like the idea of tights and this shirt. i love how it looks. its very audrey hepburn in funny face, yes?

I would wear it over a dark pencil skirt, just to see if it would work.

I don’t think I would wear it plain, because my legs are not my best feature, but I WOULD wear it belted, I think. Maybe with khakis? Or jeans and boots.

Oh, well, this morning when I read the post I didn’t enter because I thought I would look horrendous in this shirt. But I’ve been mulling it over and I think I could give it a shot. With 2 or 3 more months at the gym LOL!

I would wear it with skinnies or leggings, as is the popular choice, heels, waist cinching belt and bright, chunky bracelets and perhaps a skinny scarf to give me that long line to streamline all the volume. Hmmm…

LE, I thought about a long waistcoat but somehow the image in my head doesn’t seem too appealing to me.

I am *really* surprised by the number of people who said that they would wear this shirt. I was under the impression that surrendering the waistline is not popular amongst YLF readership. I’ll be darned. I guess belting the look gives you the option of structure.

I just saw this! I have been busy all day fitting my little marchers for their winter concert tuxedos. I would wear it and finally break down and get my first pair of skinnies to go with it!

I would NOT wear this…and I love volume, and the deconstructed look in general. But I just don’t think it would be flattering on anyone under 5′10, and the “one size fits all” thing doesn’t sit well with me. Volume has to be tailored in the shoulder, and how can “one size fits all” be tailored for everyone? I’m surprised at the amount of takers, but I can’t help but feel like it is going to be totally wrong on most of the respondents. I hope whoever wins proves me wrong.

I guess this is one way to tell how many readers you REALLY have. Offer them something free and they’ll all start coming out of the woodwork!

Hmmm, interesting idea… I bought an aubergine men’s shirt in France during the bi-annual sales in July for €3, only because it (strangely) fit really nicely on my small shoulders and looks great belted. This shirt reminds me a bit of the lines of my other shirt, and I would wear it with skinnies, a belt, great earrings and my new suede magenta ruffle ballet flats!

I would wear it with black leggings and a belt — I need something to get those leggings on me. I bought them because Angie said so !

I would wear it, just like I did back in 1982-1985. I love this fashion year. Takes me back to my 20s.

Hmmm, I wouldn’t wear this either … I like volume but not a “one size fits most” item. LOL Also, when I’ve tried on volume done in non-drapey fabric, it just makes me look big, not unstructured. Its like stiff fabric actually has a large structure built into its “unstructured” volume.

It does remind me of the 80s and 90s. In college in the 90s, I wore a large plaid or denim shirt with leggings and oxfords. I realize the fashionistas here have a better sense of remaking that trend, and I look forward to seeing the winner model her new look.

I would totally wear this! I love the length, and since I am such a short-arse I would definitely try wearing it as a dress.

I would wear it while painting a large canvas – the loose fit of the shirt wouldn’t impede my energetic brushstrokes! I’d also wear it to the farmer’s market, with black skinnies, ballet flats and the sleeves rolled up.

Interesting, I have a different philosophy on volume than some of the other commenters – if I go with a voluminous piece I wouldn’t wear a belt with it, if I want a waistline that badly I just wear something tailored.

I would wear it, but it would take lots of experimenting. I’m thinking leggings but no belt. Maybe a shorter vest. Flats or booties.

OOPS!…My previous post did not include EXACTLY the word I would wear it…
Sorry!
I would wear it…yes I would
Out the door and through the neighborhood,
To the store, to the mall
Shopping, lunching, anywhere at all…
What a treat to behold,
I would wear it…the best of all!
(it’s early…ha)

I would wear it with leggings, slouch boots, and a few long chains.

I would wear it! I’d probably go with a look similar to pic #3… wide belt, skinnies and heels!

This looks like a great shirt for spring/late summer fall. I would wear it with dark skinny jeans and flat calf length boots, chunky necklaces or scarf, and maybe a few top buttons undone with pretty textured camisole underneath for texture. Or calf length leggings and shorter heel/ballet flat. Or tiny shorts and interesting boots! Love it!

I would wear it – with skinny jeans and high-heeled boots, belted, with a chunky silver accessories. Love it

I would wear it … with leggings! At 5′3”, I am guessing it will almost come to my knees, which is the ideal length for leggings. Oh, and boots! This could be the opportunity to finally try the waist-hiding look, which I adore on others, but haven’t mustered the courage to wear myself yet. Mmmm … and an open cardigan over it … now I really want this shirt … also, the name is irresistible!

I would wear this on the weekends with bright leggings and flat riding boots! I’m starting to get into big over small silhouettes and this would be a great way to rock the look!

It’s absolutely gorgeous! And yes, I would wear it.

I would wear it because since I’m surrendering my waistline already to pregnancy, I might as well wear a big shirt, right?

I would first get this shirt hemmed because I’m short (just under 5′3″) and I would wear it with straight jeans, cute flats, and belt it (over the hips or at the waist, not sure yet). I’d finish the look with cute earrings.

ooo it’s gorgeous! i would wear it tucked into a high waisted skirt, Carolina Herrera style, open over a body conscious dress, or with skinny jeans and tons of necklaces. such a great basic!

I would wear it!

Its so cute. I would wear it with my skinny black. I would wear my jeans tucked into boots. What a classy outfit.

I’ve been looking for a shirt like this to see if i can adapt to the style but i would wear it belted and probably with skinny jeans for a balanced look.

I would wear it! I am petite, so I will wear it with my snake skin legging and pump!
A shirt says “I don’t care ” better than a dress.

This reminds me of an updated version of a shirt of my mom’s I used to steal when I was young. I loved that one, and I love this one. I would wear it belted, and it would give me a safe way to try skinny jeans (a style I’ve been resisting – it strikes fear in my heart even though I love the look on others). Oooh, I’d wear with brown leather bootie and a red bag. Thanks for the drawing!

Wow this giveaway is popular!! A different look for a lot of us I am sure! I would wear it with skinnie jeans, ballet flats and an elastacised belt. If I had a moto vest I think that could be a good pairing as well.

I would definitely wear it!

I would wear this white blouse everywhere and anywhere. A white blouse goes with everything.

Yikes, let me be part of the small minority that says, I would absolutely NOT wear it (for many reasons some of which have already been mentioned).

Oh, neat. I love this kind of look. I would wear it with skinnies and my pale gold metallic Clarks ballet flats, sometimes with a wide black belt and sometimes unbelted.

i would wear it. it would be all about the belt, shoes, jewelry, or scarf. fun.

I would wear it belted as shown!

I would wear it both with and without a belt. This is fun look that I can easily wear in my everyday life; a comfortable look that can look chic at the same time.

I’d wear it with sequin leggings and heels!

I would wear it with a belt, skinny leg jeans, and my black wedge heels. Love, love, love that the baggier look is coming in.

Wow! What a response. Thank you for all your entries. The giveaway is now closed and we will announce the winner by Monday.

[...] was blown away by the number of entries to the Zina’s painters shirt giveaway. My guess was that this level of garment deconstruction would not be popular on YLF. What a [...]

[...] style is not as voluminous as the painters shirt, but not all that tailored either, meaning you’ll get away with a boxier silhouette. In fact [...]