Four Mistakes That Are Stopping You from Embracing Oversized Dressing
Skeptical of oversized dressing? Here are a few common mistakes—and how to fix them.
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Do you ever spot a woman in wide-leg pants or a slightly slouchy sweater and wish you could pull off her nonchalant look? I love to break it to you: You can. Oversized dressing is not reserved for ultra-trendy twenty-somethings, nor will it make you look frumpy. Rather, the right combination of relaxed pieces has the power to create incredibly chic proportions at any age.
If you’re eager to experiment with oversized dressing but not sure where to begin, the key is to follow a few simple rules of thumb—inspired by our co-founder and Chief Creative Officer, Miyako Nakamura. Relying on an unofficial uniform of menswear-inspired shirts and perfectly draped trousers, Miyako is our resident queen of oversized dressing. After years of observing her style, I’ve learned that pulling off an extra-relaxed look is less intimidating than you might think. Just stick to these four dos and don’ts—which will ensure you look put together while giving off that laid-back je ne sais quoi.
Do: Incorporate one fitted piece.
If you’re worried your oversized outfit is starting to veer into sloppy territory, switch out one piece for something more fitted. You’ll be surprised how this simple swap instantly brings balance to your ensemble and allows your remaining oversized silhouettes to really shine. For instance, wide-leg jeans and an unbuttoned poplin shirt create a crisp, Nancy-Meyers-approved combination, while a streamlined underpinning complements your billowy top half. Just slip on some polished sneakers and fasten your favorite gold hoops to go from cutting flowers in the garden to grabbing drinks with your girlfriends.
Do: Start with subtly oversized styles.
To avoid overwhelming your frame, start by going up one size. If you end up wanting an even slouchier fit, you can always go bigger, but sizing up once usually does the trick. Or, if you really want to take things slowly, don’t size up at all, and instead, opt for a style that’s slightly oversized by design, such as the boyfriend-style O’Hara blazer. To keep the focus on its beautifully boxy cut, complete your outfit with streamlined essentials like the Choe top, Archie jeans, Zelda boots, and Claressa hoops.
Do: Invest in tailoring.
“Never settle” is always good advice. When it comes to your closet, this guidance means you should only keep items that work from the start—or will after some tailoring tweaks. If you love a pair of long trousers, go for a pseudo-oversized look by leaving them slightly longer than you normally would, hemming them just enough that they don’t hit the ground. If you want to wear a boxy-in-the-best-way tunic, have the cuffs taken up if the sleeves hit below your wrists. The goal is to look like you confidently selected unique silhouettes—not like you accidentally ended up with ill-fitting items.
Do: Stick with mostly neutrals.
When in doubt, focus on one major statement element per outfit. If you want to wear an oversized style, let the silhouette speak for itself, and go easy on the vibrant colors and bold patterns. If you want to cozy up in your favorite oversized cardigan but tend to like color, try layering your sweater over the fitted Axam turtleneck and sleek Skinny Fosters. The pants add a touch of neutral color, while accessories like the Rowan flats and Yuna earrings add a warm, rich pop.