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Quick Overview
THE BUTTON DOWN for guys is getting a little roomier this fall, and I’m into it. If you need an example, just take a look at Harry Styles who wore one of his gloriously billowy white shirts in September. The look that I’m seeing on him and on men in public is all about the dropped shoulders, sleeves that balloon ever so slightly at the cuffs, a roomy body that still skims the torso, and enough extra fabric to make a half-tuck look really good. It’s slouchy and a little hot, but still dressy enough to wear with trousers, a pair of jeans, or basically anything you’d normally pair with a button-down.
The trick is making the extra fabric look intentional, instead of looking like a shirt you accidentally grabbed the wrong size. You can buy a shirt that’s already cut oversized, or take a breezy, relaxed button-down and size up than your usual fit for a similar effect. I like mine with the sleeves rolled, and sometimes with the front half-tucked, and the rest left loose. The options of shirts out there are endless for guys who want to achieve this aesthetic (you can head to any of your shopping outlets or thrift stores), but some of the ones we’re loving from our favorite menswear brands are listed below.
1) Reigning Champ Cotton Poplin Alumni Standard Shirt
Here’s where you can cheat the system a little. The Alumni has a more traditional standard fit, so instead of shopping specifically for an oversized shirt, size up to create that extra room through the shoulders, sleeves, and body. It’s a good reminder that you don’t necessarily need an “oversized” label to get the look.
2) Cos Oversized Striped Cotton-Poplin Shirt
Cos
A classic oversized button-down in the kind of crisp cotton-poplin that makes the whole look feel like effortless. The stripes add a little visual interest, while the generous cut gives you those dropped shoulders and roomy sleeves that make this trend work.
3) Relaxed-Fit Denim Shirt
Denim is an easy way to make the oversized button-down feel a little more rugged. This one has a relaxed fit that works especially well worn open over a tee or loosely tucked into jeans, and the heavier fabric gives the extra volume some structure.
4) Uniqlo Striped Oversized Shirt
Uniqlo is already doing the work for you here. This shirt is designed with an oversized, boxy silhouette, so you don’t have to play the guessing game with sizing. The stripes keep the roomy proportions from feeling too plain.
5) J.Crew Overlap Button Down Shirt
This is a slightly more couture take on the button-down, with its overlapping construction giving the classic silhouette some extra shape. It’s a good option if you want the loose, drapey look without going full-on enormous. I’d also say it’s great for more high-end occasions (though you can get away with it leisurely, too).
6) All Saints Carlyle Long Sleeve Oversized Shirt
AllSaints does that slightly undone thing well, and the Carlyle fits right into that aesthetic. The oversized silhouette gives you plenty of room through the body and sleeves, making it the kind of shirt that looks better a little rumpled than perfectly pressed.
7) California Arts Del Mar Oversized Shirt
This one really leans into the billowy side of the trend, with a wide, relaxed fit and dropped shoulders that give it that intentionally oversized shape. It’s the shirt I’d reach for when the goal is to look like I’m swimming in fabric, but in all the right ways. This is closer to the one Harry Styles wore earlier last month.
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