Chasing the Dream of the Perfect White Shirt

Here’s what I know now, after years of running.

Hey Mrs. Solomon
7 min readFeb 5, 2023

I remember the summer before law school when I worked in the shoe department at Ralph Lauren in Philadelphia. My manager said that you never just hand someone a pair of shoes because you’re not selling a pair of shoes. You’re selling the life that you could have in those shoes. “You don’t just say, here are your sneakers,” she said, dead serious. “You say: ‘Here are the sneakers you’re going to sling over your shoulder when you drive your vintage MG to the beach.’ ” Those were heady times.

in my Acne shirt, Old Celine pants, Prada brogues, Bao Bao bag (all secondhand)

But I think there’s so much truth in the idea that buying clothes is never just buying clothes. It’s always about trying to tap into the self you want to be. There’s so much emotion in it. Sometimes it’s nostalgia for the way you felt at a certain time. Sometimes it’s the opposite: It’s dreaming forward about who you might become. Either way you’re thinking about the way you want to feel and imagining that somehow this piece can launch a chain of events that takes you there.

This might never be the case more than when it comes to the quintessential white shirt. I could write a whole separate thing on a white T-shirt, but this is about a very specific white shirt. The white button-up shirt.

Take a second now and picture how it is in your mind’s eye. I imagine that, across so many very different styles of dress, our pictures are the same. It’s a classic, universal item and feeling. I know I’ve been chasing it, catching it, and chasing it again my whole life.

You can find so many compilations of iconic white shirt imagery. The Flair Index comes to mind, because Jennifer Alfano is so much about these quintessential pieces. Her images, here.

Whenever I open questions on my Instagram, someone asks about finding that white shirt so I thought I’d focus on that here. And tell you what — after all this trial and error and Eureka — I know for sure right now.

(1) There has to be a mannish element to it. So a true, classic collar (button down optional). Buttons all the way up the front not some funky half button tunic. Traditional button cuff with working buttons. Borrowed from the boys looks or actually from the boys. And I always caveat this by saying “mannish” is a tool word that I use to describe a certain kind of look and feel, because in reality, all clothing can be for all genders. But when I think about the perfect white shirt, I think it’s no coincidence that this element is always there. I think about the closet full of white shirts in The Great Gatsby, or Annette Bening borrowing a shirt from Warren Beatty in The American President.

It’s the style that’s the most useful because it’s got such heritage. It also has an appealing “wrongness,” an inherent friction, that comes from taking something commonly seen on a boardroom grandad and deploying it on you with all your “you” materials, prints and un-grandpa elements.

2. It can’t have darts. Or a slim fit. What so appealing is the sense that you’re not trying too hard. And the shape that’s created from the billowing. This is generally the big in your big, slim, skin … I’ve tried a million slim versions and I always end up hating them. Darts are too femme. You lose your friction.

In fact, it has to be oversized. It can be a little oversized, or it can be totally oversized — more on that here. (Both work for different things, for different ways of feeling. And in the end you may want to have more than one on hand for different things you want to achieve with it.) Specifically, you don’t want the shoulder to sit on your actual shoulder. It should drop below. And you want the cuffs to be headed towards your hand or even lower. Even if it’s super big, you won’t look like you’re wearing your father’s shirt because you’re going to be manipulating it (tucking, belting, rolling, etc.). You’ll get some definition at the waist when you tuck it and you’ll get a sort of Japanese cool when you don’t.

3. It has to be cotton — once again, I’ve tried a million other things. And I didn’t want this to be the case. I hate how high maintenance a white shirt is. Remember how Elaine on Seinfeld felt when her Today Sponge was discontinued and became so hard to get? Suddenly every potential date had to be “sponge worthy.” Sometimes I catch myself not wearing my treasured white shirts or asking, “Is this day white shirt worthy?” Every time I’ve put a drop of cover up on my face it ends up on my white shirt. But maybe its difficulty is why it’s so magical and wonderful. There’s something inherently dreamy about an item that looks so easy and yet is so high maintenance but so wonderful that you just can’t ignore it. The cotton captures that. It also signals mannish. It also feels incredible. Especially soft or Pima cotton vs. the stiffer cotton weave of a traditional Oxford cloth shirt — though those are good, too, if that’s your preference.

4. When you put on your shirt, it should feel comforting. You should instinctively start manipulating it, playing with buttons, unbuttoned or buttoned, rolling the sleeves or shoving them up, tying in the front or in the back, tying in the front then pushing the tie underneath, tucking in all the way part of the way (one tail, just the front, etc). Now go to your skirt rack and start trying it on with them. It will work with any one. Probably any pair of pants too.

ohhhh, Audrey (via British Vogue)

I currently have three favorite white shirts. Two of them are old Raf Simons men’s — one is the thicker, oxford cotton, and one is the thinner/ smoother; they’re both very oversized. I wear the smooth one almost every day in the summer in New England. It becomes a jacket over a dress. It becomes a beach cover-up. The length goes past the length of my jean shorts so it gives me this extra sense of security, and makes a more interesting profile, I can turn into it kind of jacket for a restaurant. The stiffer one is good for nighttime when it gets a little cooler.

For a white shirt that’s closer to regular size I have an Acne white shirt that I love. It gets better and better the more you wash it; the cotton is not threadbare, but definitely smoother than smooth. It’s very floppy, so it doesn’t hold. It’s hard to roll up the sleeves; they won’t stay, so it’s best to just shove them up and tuck them under or let them flop around your fingers. When I made this reel about skirts I noticed that without trying so many of the skirts I paired with the shirt, it’s got this no-style style that is so stylish and what I mean there’s nothing extra, there’s nothing trying; there’s nothing special that you can see on the outside but yet it’s so special.

Additional ideas + considerations:

-Is there a monogram option? Get yours, your s/o’s, or even a funny word like YUM or WTF. So cool.

-Don’t get shoulder pads. Or add them. (See also, darts, above.) But do toss a shoulder pad tee under if you want.

-Try something fun underneath the thin cotton ones like a hot pink bra (above) or colorful sports bra.

-You might try a men’s extra long if you want something closer to a shirtdress or think you’ll use it as a coverup.

-If you’re feeling really determined, order a bunch from Netaporter or Shopbop (lots of brands, easy returns) and then you’ll understand brands/sizes and can keep what you wish.

-Because they’re so hard to keep clean, carry a Tide stick. Try getting away with spot cleaning, airing out/steaming wrinkles in the shower, Downy Wrinkle Release, and fabric refreshers.

-Definitely take your white shirt out to dinner, after which you can hang it up and easily get a second use.

-I’m all about #secondhandshopping but don’t try to buy your white shirt secondhand unless it’s in pristine condition or new with tags. So hard to keep clean. Don’t start with someone else’s stains etc.

-If you were thinking about a true “blouse” consider a shirt instead. It’s cooler. But for that, I rec Another Tomorrow.

-If you were thinking about a shirtdress... I actually don’t think the label is super important. Mine are The Frankie Shop (sold out but ask to be notified; they bring them back) and LouLou Studio. Try the Outnet. This item is pretty forgiving! You rarely will wear it (if ever) as is, the way you can a white shirt. You’ll be belting it and layering it, unbuttoning it. Keep it simple. Make sure it buttons all the way up. You may want a long and midi version, sleeves and no sleeves.

-A few great resources. Don’t miss this take from Leandra Medine. Or this from my friend Christine, writing for The Quality Edit. Read The New Garconne by Navaz Batliwalla (omigoshsogood). And then discover her blogggg. Read The Cool Factor by Andrea Linett. It’s still so relevant and enjoyable to own. And I Love Your Style, by Amanda Brooks. Pure delight.

Did I miss anything? Drop any notes/thoughts/questions below. As I type this I’m eating beet hummus in my white shirt. May the force be with me and you as well.



Hey Mrs. Solomon

Grown-ass woman. Perpetual student of style. Sharer of tips. I work @honorcodecreative and write about fashion and style ahas here and on IG @heymrssolomon XO.