How I Found Our New Best in Class Button-down
Under my stewardship, our Best in Class button-down has long been Ayr’s The Deep End. It has all the hallmarks of a great one, including a weight that reminds me of the vintage Ralph Lauren shirts on eBay. Our senior writer Lauren Ro agrees that “the shirt’s proportions are just so good.” (Influenced by my review, she got herself one in white and another in blue.) The care instructions are easy, too: “Machine wash cold, do not bleach, tumble dry low, cool iron if needed”; it can handle a regular cycle through the dryer and a steamer to get rid of any remaining wrinkles. When I first named it our best overall in 2022, it cost $125, and today it’s $165. Last year, when the shirt was marked up to $145, I started wondering whether there was anything better — for cheaper. I wasn’t looking for a replacement per se; I was looking for an upgrade. Over the course of several months, I tried out a few new (to me) button-downs: Old Navy’s Oversized Button-Down Boyfriend Shirt, Gap’s Organic Cotton Oxford Big Shirt, and L.L. Bean’s Essential Cotton Poplin Shirt and Wrinkle-Free Pinpoint Oxford Shirt. They’re $39.99, $69.95, $64.95, and $79.95, respectively.
Beyond obvious points like size range (I hoped to find something available in more sizes than the standard range of XS to XL) and fit, the deciding factors of this hunt were wearability and versatility. I can’t afford the dry-cleaning bills of one of Truman Capote’s Swans, so the shirt needed to be machine washable, too. I even performed a laundering test recently: washing all the contenders together and seeing how they came out of the dryer. Ultimately, I did find a new — and better — Best in Class button-down. (For reference, I’m about five-two and usually wear a medium. I’m intimately familiar with “boob gap”; do with that information what you will.)
My Top Picks
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The Wrinkle-Free Pinpoint Oxford Shirt is so crisp, it didn't wrinkle even after a dryer cycle.
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The runner-up has the closest resemblance to our former favorite button-down, Ayr’s The Deep End.
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I'd call Old Navy’s shirt a "springweight" — ideal for the next few weeks.
The just fine: L.L.Bean Essential Cotton Poplin Shirt
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In this round of testing, the lone button-down I tried that wasn’t made of 100 percent cotton was L.L. Bean’s Essential Cotton Poplin Shirt. Don’t fret yet: It’s 95 percent cotton and only 5 percent spandex. If I didn’t know about the 5 percent spandex, I’m not sure I would have thought of this as a particularly stretchy shirt. In reality, the fabric composition accommodates movement — I wouldn’t jump in the shirt, but I could. That said, it’s the thinnest of the shirts I tried. It’s not entirely skimpy, but if I had on a black bra underneath you could tell (very clearly at the right angle). For that reason alone, it’s out of the running for our best overall. Another deduction: how rumpled it comes out of the dryer (it’ll need a good steaming after washing).
The good: Old Navy Oversized Boyfriend Shirt
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Old Navy’s Oversized Button-Down Boyfriend Shirt is not what I imagined it’d be. Lured by “100 percent oxford cotton” like a mermaid tempted with legs by an octopean witch, I feel a bit like a fish in a net here. To me, “100 percent oxford cotton” implies something sturdier, hardier, and just a tad rougher. This isn’t the oxford cotton I expected. It’s light, as in a fairy’s wing, a slice of angel-food cake, or a sprig of baby’s breath. It’s less sheer than L.L. Bean’s Essential Cotton Poplin Shirt. (It comes in both “poplin white” and “oxford white” — I’m wearing the latter.) I’d call it a springweight. I can’t imagine wearing anything better when it’s between 61 and 73 degrees. It’s $39.99 at full price and marked down to $23.99 pretty frequently. I can forgive how wrinkly it is immediately out of the dryer, as it looks nice wrinkled. Our contributor Mya Gelber, who also tried the shirt as part of a hunt, says, “This is a great inexpensive option if you’re looking for something to throw over a swimsuit or for a stroll to the farmers’ market.” That’s exactly what it’s meant for. It’s available in sizes XS to 4X, and you should size down — I sized down to a small so it looks borrowed from someone else.
The better: Gap Organic Cotton Oxford Big Shirt
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I liked the linen Big Shirt (it’s now sold out, but it got me through the summer of 2024) and I love Gap’s cotton oxford Big Shirt — plus, it’s the shirt I’ve been trying out the longest, since last May. If your platonic ideal button-down is oversize, this is the button-down for you. I requested mine in a size medium and could’ve gone down to a small. It’s generously sized and does lean casual because of that. I understand why it has over 1,000 five star ratings! It has the closest resemblance to Ayr’s The Deep End — for $95 less. After almost a year of testing, it doesn’t show any signs of wear (not even any yellowing of the fabric). Compared to the Old Navy oxford, it’s mightier, heartier, and weightier.
[Editor’s note: Some sizes of Gap’s Organic Cotton Oxford Big Shirt are sold out now, but every size of Gap’s Organic Cotton Poplin Big Shirt is in stock.]
The best: L.L. Bean Wrinkle-Free Pinpoint Oxford Shirt
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Not to sound like a crumpet-eating English curmudgeon, but I miss the air of formality traditionally associated with button-downs. L.L. Bean’s Wrinkle-Free Pinpoint Oxford Shirt has it in spades. As a shirting material, a pinpoint fabric falls between a broadcloth and oxford cloth (a Drake’s pinpoint shirt can start at $345, for comparison). L.L.Bean’s pinpoint is, to borrow a phrase from our writer Erin Schwartz, “so crisp you could crack an egg on it.” Quite literally: I spilled a half-full glass of water on it, and the shirt dried itself out and remained smooth. The white resembles the stiff peaks of a meringue, and the collar appears starched (like a vicar’s, or Josh O’Connor’s Mr. Elton in Emma). Is this how Sofia Coppola feels wearing a Charvet shirt on a shoot? (For reference, I took this in a medium; I didn’t need the petite medium.)
Now, “wrinkle-free” is a big claim from L.L. Bean, and part of the marketing strategy — evidenced by a green sticker printed with “wrinkle-free” when the shirt arrives. The cotton is specially treated to resist wrinkles. (I reached out to hear more about what the process involves, and I can update this accordingly with any specifics.) Does the shirt come out magically unwrinkled out of the dryer? No. But it’s impressive how much less wrinkled it was compared to the others. I actually messaged our staff Slack channel after the experiment that I hadn’t felt this rush of scientific excitement since making a volcano explode in eighth grade. The collar (which I’d argue is the worst thing to steam over on a button-down) looked untouched after the wash.
If a “pleasure to be in class” suddenly turned into a button-down, it would be this. I’m not the only one who likes it, either. Gelber also named it a winner. “It has stiff cuffs as well as reinforced buttons. It comes in a thick cotton that is not transparent or sheer with a single back box pleat and a classic straight fit,” she said. I agree with her that it’d fit right into a corporate setting. But you can easily layer it with a cashmere sweater, for example. Or have it tucked inside the waistband of a pair of jeans. Keep the sleeves cuffed to the elbow, even. It can be nearly anything you want it to be — and that’s why it’s my new Best in Class pick.
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