Oversized button-up shirts are as much as a wardrobe classic as they get. Worn correctly, the flattering piece adds an air of effortlessness to any outfit. But figuring out how to style an oversized shirt can be perplexing—even for the most confident dresser. A too big button-up, without the right accompaniments may swallow your silhouette or look sloppy. Meanwhile, something too short or small will just look off. Don’t worry, though, you’ve got this!
The key to wearing a big button-up often lies in the layers—and experimenting with size. Some brands have styles that run large, so size notes will recommend sizing down. You might like the fit of a certain button-up but not find it relaxed enough for the look you’re going for, in which case sizing up is key to achieve that casual cool.
Once you’ve figured out the sizing, adding extra pieces like a shorter sweater on top, that subtly emphasizes your waistline, or a belt and high waisted jeans, will help. If you’re pairing a button-up with, say, a loose pair of trousers, it will help to show a little skin. We like wearing ours open, over a simple white tank. Or, you can commit to the bit and go long and lean by pairing an extra long button up with a flowing maxi or slim trousers. For more easy styling tips and tricks on how to style an oversized shirt, look no further than our edit below.
Vogue’s Favorite Oversize Button-Up Shirts:
- The Bold Blue: Toteme Organic Cotton-Poplin Shirt, $440
- The Classic White: J.Crew Étienne Oversized Shirt, $98
- The Rich Burgundy: Alex Mill Jo Shirt in Cotton Poplin, $145
- The Polished Black: The Frankie Shop Lui Organic Cotton-Poplin Shirt, $185
- The Sleek Stripe: Róhe Stripe Cotton Oversized Cuff Shirt, $480
With High-Waisted Jeans and a Belt
In this look, high-waisted denim and a belt will emphasize your waist, so you don’t feel swallowed by a big button-up. You can wear yours tucked in or open over a white T-shirt. Heeled boots help give a little extra height, too.
With a Sweater and Miniskirt
This sweater, skirt, and shirt combination is cute in a subversively preppy way, but it’s also lesson in playing with proportions. A sweater that’s slightly shorter than the button up will, again, emphasize your waist and add a bit of texture to your look. Tights and a long overcoat work well here too to protect you from the elements.
With a Fitted Tank and Wide-Leg Trousers
To balance out the volume of a button up and wide-leg trousers, we suggest wearing the shirt open with a sleek white tank underneath. This allows your look to retain an a sense of effortlessness, while still showing a bit of your shape.
With Slim-Fit Trousers and Pointy Mules
This look leans into the easy elegance of a button up, by keeping it monochromatic and sleek. Slimmer trousers on the bottom half will keep the look feeling sleek and not sloppy.
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With a Long and Lean Maxiskirt
This elegant outfit is all about extra long layers. Keep the maxiskirt lean and narrow, rather than full, to avoid swimming in fabric. Wearing your shirt slightly open at the bottom will continue the line of your legs, allowing you to look even longer.
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