8 Effortless Ways to Style an Oversized Shirt

Baggy is back! The oversized shirt trend is holding steady and styling it is easier than you think.

Published December 22, 2023

You're not drowning in all the new trends there are to keep up with; you're as much of a style maven as you ever were. Now that oversized button-downs, T-shirts, and sweaters are making the rounds again, you've never been more ready to tackle a trend.

But, if you need reminders on how to style an oversized shirt, just try one of these simple fashion tips.

Layer an Oversized Button-Up Over a Dress


Oversized button-ups give us all the 90s vibes and we aren't mad about it. Slide yours over a slip dress or T-shirt dress for a casual and playful look that's on trend in every way.

Quick Tip

Platform loafers bring this 90s look full circle. Don't forget your beaded bag! 

Pair an Oversized Tee With Bike Shorts

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We can all thank the cool mom aesthetic and the popularity of athletic wear for making bike shorts happen again. An oversized T-shirt is the perfect way to balance the skin-tight shorts and keep your casual style looking effortless.

Layer It Over a Crop Top


Middriff-bearing tops "cropped" back up a few years ago and they're still going strong. If you prefer to ease into the crop top trend, an oversized cardigan or button-down helps you feel confident while trying out a new look. Don't worry, the oversized look is so in vogue that you won't lose any fashion points for sporting the combo.

Go Oversized From Head to Toe


If you plan to fully embrace the oversized trend, you may as well commit to everything oversized in your outfit. Slip an oversized shacket over your large tee and pair it with loose-fitting pants for a comfy and stylish look. If this gives you all the Y2K vibes, that just means you're doing it right.

Add an Oversized Sweater to Your Lounge Collection

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Can we have a moment of praise for the fact that lounge wear is considered fashion now? We had no idea comfort and style could be so easy.

If you've recently started investing in lounge wear, it's time to add a cozy oversized sweater to your collection. Whether you pair it with comfy leggings or soft matching bottoms, you'll be relaxing in style.

Pair an Oversized Sweatshirt With Leggings

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For the mom on the go, the college student rushing to class, and the fashionista out for errands, this combo is always a winner. When the weather cools down, swap your usual oversized T-shirt for an oversized sweatshirt. Throw on your favorite pair of leggings and you're ready to go.

Helpful Hack

Take this look from comfy and casual to a sporty style statement by swapping your usual leggings for a leather variation.

Try Layers of Oversized Pieces

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Your slightly oversized long-sleeve tee is just begging to be paired with a sweater vest: make that an oversized sweater vest. Layers of oversized pieces can look chic as long as you choose the right ones. If you feel the combo is a bit too baggy, you can always pair it with tights or leggings.

Quick Tip

If you go the tights or leggings route, tall boots would complete this stylish look.

Embrace Wide-Leg Pants


Skinny jeans will have their day in the sun again, but for now, it's the era of the wide-leg trouser. The good news is that your oversized sweaters and button-downs pair well with the flowy bottoms. From work to weekends, this casual look gives off the coastal grandmother and old-money vibes currently on trend.

Discover Your Oversized Style


We love a pretty blouse or fitted blazer, but there's a certain effortless charm that radiates from an oversized shirt. Whether it's a sweater and skirt combo for the fall or an oversized T-shirt over your summer swimwear, you'll be rocking this trend with confidence all year long — now that you know how to style it.

8 Effortless Ways to Style an Oversized Shirt