white shirt // crease front jeans (for a full review of the jeans, read here)
Time was, when a button-down shirt was simply that: the stiff-collared element to a three-piece-suit puzzle worn to formal events. But as with most things women now can’t live without, we have Coco Chanel to thank for domesticating them. She swiped the shirts from her lover’s back—bespoke ones from Charvet, at that—and worked them into her early women’s collections. Fast forward to today’s boardroom-to-beach mainstays, and while Charvet is still the pinnacle (you can find pre-loved ones here), there’s a host of others floating around with the softness of a t-shirt and details to rival an evening dress.
That may be exciting in theory, but much like the perfect T-shirt or the perfect pair of jeans, finding the perfect button-down shirt in an ocean of contenders can feel like an exhaustive hunt. You’ve seen it in a magazine or, more likely, somewhere on social media, but it was styled just so, worn with a specific something, and now, recreating the look at home (much like trying to maintain a new haircut after the first wash) feels like a feat too far to manage.
It’s wardrobe conundrums like these that get me excited, because there’s no one-size-fits-all eureka shirt that does all the jobs you want it to, meaning the whole debacle requires a bit of an external investigation.
So for the fourth installment in this series (see the first three at the bottom of this article), I roped in some Substackers to offer the lowdown on their favorites, so you can easily find yours.
1.THE TUCKABLE & LAYERABLE SHIRT
side button shirt / jeans / shorts
I’m newly in love with this side-button shirt (above left). I’m slowly embracing more color, and discovered this dusky rose stripe is more flattering on me than blue, or even black. For some reason, classic shades on classic pieces can make me look weirdly corporate, even though I love the idea of wearing a black shirt (more on that from someone who can and does, further down).
This shirt’s so light and airy, it feels cooler than most of my summer tees. It’s 100% Portuguese cotton, has a boxy, drop-shoulder fit, and side-button details that are finished with a grosgrain ribbon trim.
I’ve always gravitated toward longer, leaner pieces on top (see my shirts below), but I’ve also been trying less oversized pieces recently, and liking the results. The shorter length makes it easier to tuck into jeans* (top left), while opening the side vents leaves room to layer it over another shirt without any bunching (top right).
*The jeans are Agolde, but if you’re a size 23 or 28, shop them here so you don’t have to pre-order & wait.
2.THE SUBTLE STATEMENT PIECE
white shirt / striped orange & white shirt
This scarf shirt (top left) feels a touch more casual than a Tuxedo option while riffing on the same idea. It’s by ex-Calvin Klein designer Manel Garcia Espejo, who’s now behind The Salting, with husband, Michael Ward. Everything is made in New York. And while those strings can be tied in a bow, I prefer to leave them loose—that way, they look like a gentleman’s bowtie, left undone, at the end of the evening. (Similar options here, here, here and here).
This Zara shirt (top right) buttons at the back and can be undone at the top and held closed with a button-able string. The pocket sits satisfyingly low at the front, too. I rarely find anything in Zara these days, but this shirt is an anomaly that feels like it came from elsewhere.
3.PLAIDS & STRIPES
In a timely move, considering the pre-fall and fall runways were covered in it, I’ve been pairing plaid shirts with Bermuda shorts this summer. Shirts like this (top left. Warning: it’s final sale, but it’s so good, that if you know your size in this brand it could be perfect) and also this (top middle), or this (top right)—I love the side cut-out detail and blurry print.
4.CLEANING TIPS
For immediate, on-the-sport stain removal, I use this clean-ingredient spray. But for the tricky ones, or marks that can’t get treated til a day or so later, I just go straight in with this and it’s never failed. For any day-to-day shirts, including the Zara one above, I wash in this, hang out to dry and then iron. But for the other shirts pictured here, I drop them off with the dry cleaner to keep them looking crisp; it’s the best way to achieve that smooth, uncreased look.
The Handmade Tuxedo Shirt: Sierra Goodhue of HODGEPODGE
Tell me about your favorite shirt…
For around two years I’ve been on the hunt for a perfect tuxedo shirt. I love that its a step up from a basic button-down, with details that offer more flair and playful styling options. I found the perfect one at Maison Treize, a small brand that hand-makes shirts in Spain. This Opera design stood out because it’s unisex, and that sizing usually gives me the best fit. I like a drop-shoulder and boxier cut, and sizing up in women’s just makes it longer instead of wider. (Find similar options from Jamie Haller here, Ralph Lauren here, or 6397, here).
What’s the fabric composition?
It’s made of 100% natural fibers so it’s a thicker structured cotton like a true tuxedo shirt. The collar and sleeves are super thick and crisp, and the bib is its own separate entity that juts out a bit for great dimension.
How do you style it?
My secret sauce is juxtaposition. So, I’ll pair this formal shirt with a catfish-bottom gym short, or lean into traditional formal styling and make a true “tuxedo” of it. Since it naturally reads more masculine, I love styling it to feel more feminine.
How do you wash and take care of it?
Honestly, I haven’t washed it yet. I’m a firm believer we wash our clothes too much, and I’m only in it for a few hours at a time. Most of my “clothes clothes” don’t make it into weekly laundry; I take them to the dry cleaner once a month or hand wash as needed in the bathtub. If there’s a stain, I spot clean.
The White Boyfriend Shirt: Robyn Merrett of Spoonful of Style
Tell me about your favorite shirt…
I live for oversized silhouettes. It’s the easiest way to capture ease, especially in a button-up. They’re versatile, classic, and timeless. Mine is the Max White Cotton Shirt from Dissh, one of my favorite brands for elevated basics. I got it about two years ago, so it’s sold out now (similar version here). I’m on the curvier side, and the way it hits around my hips rather than covering my figure gives me relaxed structure while still letting my body shine.
What’s the fabric composition?
It’s lightweight but not flimsy, and always feels crisp, which is nice paired with capris or baggy jeans, because there’s still shape and structure. It washes well and hasn’t lost its form. It’s a crisp white and hasn’t dulled despite the amount of times I’ve washed and dry-cleaned it. I usually have to size up for the fit I want, but I didn’t need to with this one.
How do you style it?
I dress it up, I dress it down: capris and thong sandals, baggy jeans with ballet flats, leather pants and strappy heels, even a bikini with linen pants. I credit its versatility to its shape. You can’t go wrong with a button-up that has a little structure but isn’t starch-stiff.
How do you wash and take care of it?
I do wash at home and immediately hang it up occasionally, but find dry cleaning works best.
The Colorful Weekend Shirt: Gabriele Hackworthy of HAUTEWORTHY
Tell me about your favorite shirt…
I like my shirt to look stolen from my lover’s wardrobe. It has to have a masculine cut, never darted or fitted. Right now I’m loving the LMND Chiara classic shirt in Ink Blue, a very Celine color-coded shade (this Jamie Haller version is similar). I have it in a ton of colors, and, of course, in white.
What’s the fabric composition?
It’s 100% cotton and the perfect summer weight. I like how it’s slightly oversized with a drop shoulder and a bit of volume in the back. It finishes right on the hip, and has a yoke that dips down slightly at the back.
How do you style it?
It’s a great length for tucking and I usually wear it tucked in. I hate when shirts are really long and you end up trying to force all this excess fabric into your pants; you just end up looking bulky. The shape is very 80s. The sleeves look great pushed or rolled, and the patch pocket adds a relaxed feel. It’s loose but structured enough to wear over a roll neck in winter. The blue is the perfect Charvet-coded shade and it’s so versatile that I’ve worn it on the beach and to a fashion show in Paris.
How do you wash and take care of it?
Since it’s a less precious shirt, I machine wash on cold with a small amount of The Laundress detergent, and I like Dr Beckman for stain remover products. I save dry cleaning for my silk shirts and prefer a gentle cold wash whenever possible. To avoid makeup stains, I spray the inside collar with hairspray, and I always iron with spray starch for a crisp finish.
The Affordable Black Shirt: Jessica Boardman of JESSICA’S SUBSTACK
Tell me about your favorite shirt…
My overall pick is Gap’s Organic Cotton Poplin Big Shirt. The price is right and the fit is a classic: intentionally oversized and slightly longer, which suits my preference for relaxed over tailored. I wear it as a shirt in warmer months but also as an easy cover-up at the lake, pool, or beach. I stay true to size for the oversized look, and it’s become a great pregnancy piece without feeling like maternity-wear.
What’s the fabric composition?
It’s 100% organic cotton, so ultra breathable without feeling flimsy, with enough substance that it isn’t sheer, and it softens nicely with wear. It gives me the look and versatility I want from a button-down without requiring a major investment, especially since Gap runs such good sales.
How do you style it?
I’ve worn it to dinner, on casual weekends, while traveling, unbuttoned and tied in a knot, and as a beach cover-up. It’s one of those pieces that can become whatever you need it to be.
How do you wash and take care of it?
For stains, I use Miss Mouth’s Messy Eater Stain Treater before washing. I machine-wash with like colors in cold water using Charlie’s Soap, then dry for just a few minutes to warm and relax the fabric before hanging it to dry, and reshaping the collar, cuffs, and hem while still damp. If any areas are especially wrinkled, I mist them with water and smooth them out before hanging. It keeps the shirt looking crisp without having to dry-clean or fully iron it every time.
The Shirtdress As Coverup: Noëlly Sam of The Corageus Letter
similar shirtdress, here / similar shirt, here
Tell me about your favorite shirt…
There isn’t just one—I love a crisp white or light blue Oxford shirt, oversized and 100% cotton. I like the options from COS, Uniqlo, and Arket (which you can sometimes snag through Asos in the US).
Which details draw you in?
I can rarely resist an asymmetrical detail, a scarf or tie, an open back or long cuffs. Length is also a big factor for me, especially with shirtdresses. The blue one I’m wearing (pictured) has panels at the back that almost look like wings (no longer available, but this Comme Si one is perfect).
How do you style it?
I love the endless possibilities of a good shirt. I wear it loose with jeans, cinched with barrel pants, or layered over a dress.
How do you wash and take care of it?
With natural fabrics, which I prefer, a delicate wash and air drying go a long way. This is the natural detergent I use, and I always skip fabric softener. For mild stains, I’ll use a little baking soda and hand wash the area rather than reaching for bleach. Acting quickly always helps!
Standout Shirts
If you’re looking for COLOR:
This blue shirt is very Charvet-like, and crafted from the softest cotton.
If you’re looking for a good STRIPE:
The perfect wide striped shirt if ever there was one, with a relaxed fit made from 100% cotton (size down for a less oversized look).
Loose, easy with a slim, stripe, this shirt is called the Weekender, because that’s exactly what it’s perfect for.
If you’re looking for something CLASSIC:
Lean and loose, this one was named one of Wirecutter’s favorites last year.
If you’re looking for interesting DETAILS:
With a luxe feel (read: stiff out of the box) it boasts clean French seams, with extra long cuffs that are easy to turn up. But if left down, will add a lovely bit of drama.
I find it hard to resist an exaggerated cuff and this red shirt with tiny white stripes (hard to see in this pic!) is really showing off in that department. It’s 100% Italian linen and can be ordered made-to-measure, along with a monogramming option.
Shop everything on Shopmy, here
Thanks for reading. If you're enjoying this, please join us (new takes on styling shirts lie ahead)
HOW TO STYLE BUTTON DOWN SHIRTS NOW (NOT THEN)
A crisp white shirt can come across as a little serious, and, maybe even dull. But partner yours with boxer shorts, instead of whatever you’d usually reach for, and you get a subtle, modern spin.
This one is simple, but easy to forget. Just accessorize with some artful pieces. Keep the neckline clean, so the collar is the only detail, and do a go-big-or-go-home situation with your ears…and maybe, if you’re brave enough, your nose.
Layering shirts (like I did in the first image) adds an additional warming layer in early to mid fall, pushing out your need for a sweater until later into the season. Picking two identical shirts doesn’t have the same impact as the color and pattern play on display here—but stick to a color wheel. Earthy greens and browns in stripes and/or different checks, is slightly more casual, while a blue and white stripe layered with the same in reverse, leans more polished.
A cinch-waist shirt is obviously flattering, but it’s also more elevated, which makes it the perfect counterpoint to a dressy skirt or pants—fringed, printed, or with some kind of texture that encourages them into evening territory.
A little juxtaposition goes a long way. As is the case with the look top left. Wearing a checked shirt over a graphic t-shirt is such a nostalgic grunge move. But when the t-shirt’s a crisp, plain, high-neck crew and the shirt has echoes of a Chanel-Charvet Tuxedo design, it feels thoroughly fresh and of-the-moment.
Play with color and texture in as less obvious a way as you feel comfortable with. Forest green is one of the lesser-seen button downs I’ve come across, which makes it the perfect antidote to these taffeta Bermuda shorts.
Make it the popping color accent of your look, whatever that may be.
This is the same deal as No.3, but with pinstripes, so you can contrast the casual vs polished look.