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.
Features at a Glance
| Fabric & Material | Cotton poplin |
| Fit & Cut | Standard fit, tailored shape |
| Collar Style | Point collar |
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.
Features at a Glance
| Fabric & Material | Cotton poplin |
| Fit & Cut | Oversized |
| Collar Style | Concealed button-tab collar |
Advertisement – Continue Reading Below
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.
Features at a Glance
| Fabric & Material | 100% cotton denim |
| Fit & Cut | Relaxed, straight and roomy; dropped shoulders |
| Collar Style | Spread collar |
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.
Features at a Glance
| Fabric & Material | Cotton poplin |
| Fit & Cut | Oversized, boxy |
| Collar Style | Classic collar |
Advertisement – Continue Reading Below
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).
Features at a Glance
| Fabric & Material | Cotton |
| Fit & Cut | Relaxed, oversized |
| Collar Style | Classic collar |
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.
Features at a Glance
| Fabric & Material | 100% lyocell |
| Fit & Cut | Relaxed, slightly oversized |
| Collar Style | Spread collar |
Advertisement – Continue Reading Below
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.
Features at a Glance
| Fabric & Material | Cotton poplin |
| Fit & Cut | Oversized, wide, dropped shoulders |
| Collar Style | Point collar |
Josiah is the Digital Content Producer for the commerce team at Popular Mechanics, Best Products, Runner’s World, and Bicycling Magazine. He also writes for “BIO Buys”—a column on Biography.com—giving readers the lowdown on what products their favorite celebs are using. In another life, Josiah was an editor at ThePioneerWoman.com, where he sharpened his expertise on all things lifestyle, food-news, and entertainment. Outside work related matters, he’s a fan of Studio Ghibli films, unimportant reality TV drama, and melancholy Lorde songs.
Christian is the Style and Reviews Director at Men’s Health and Women’s Health, where he oversees shopping and style content for both brands. He started his magazine career as an accessories assistant at Vogue, and has since held editorial roles at Tatler Asia and The Manual. When he’s not online shopping, you can find him on long walks with his two corgis.
