7 Baggy Shirt Styles to Keep You Comfy

Size up for an instant cool factor.

baggy shirts


Once reserved for skaters and younger brothers, the baggy top is now fair fashion game. Balance an overtly done-up look by playing with dimensions, or channel your inner Billie Eilish and opt into all-over oversized. And preppies (think Risky Business) no longer have full ownership over the borrowed button-up look. However you wear it, a baggy shirt is the building block you need in your closet. There’s something unapologetically '90s about the trend that makes it fresh while keeping things super comfortable. When it comes to dressing for the summer, basics simplify everything—from packing for a weekend away to dressing for a Summer Friday that starts with a stop at the office. 

If you’re intimidated by loosening things up, don’t be! Start by zeroing in on silhouettes you know you feel confident in already. Love a straightforward-button down? Great, why not try one from the Men’s section? Do you always end up layering on a sweatshirt at the last minute? A baggy quarter zip just might be your next purchase. On the other hand, take chances with a new style. There’s no better way to experiment than with tried-and-true basicsRead on for seven of our favorite ways to wear baggy shirts. 

The Baggy T-Shirt

Next time you reach for your favorite worn-out tee, imagine replacing it with a larger option. Why? Well it’s certainly more comfortable, for one. It also takes an ordinary outfit and makes it 10% easier. Don’t forget to try layering it under slips and over dresses. The outfit formulas are endless. Tuck in the shirt half-way or pair with pants that won’t show the gathered material. An easy trick is to simply size up two sizes from your normal size. For the fashion forward, opt for cuts with the specific silhouette in mind.

The Baggy Button-Down

Hand over the button-down, finance bros. The classic staple has been handed off between the Bunny McDougals and the Gossip Girl-lovers long enough. Keep it easy by pushing the sleeves up instead of rolling. Pop the collar. Button the shirt halfway. What makes a modern classic is keeping things playful. The larger size makes it a perfect beach cover up or downtown off-duty look with ripped up shorts and black shades. If you’re brave, opt for a Carrie Bradshaw-esque shirt-as-a-dress look.

The Baggy Quarter Zip

Summer camp chic is happening in a big way. So stack those friendship bracelets, cross your fingers you pass the swim test, and head to the campfire in an oversized quarter zip. Avoid an overtly crunchy aesthetic by choosing bright, of-the-moment colors and statement closures. Wear it with anything you would normally wear with a denim jacket. And don’t be late for lights out.

The Baggy Crop

Consider playing with proportions this summer by taking on the abbreviated version of the baggy shirt trend. The baggy cropped shirt works under overalls or with high-waist anything. Bonus points for taking matters into your own hands and chopping the crop yourself. This is a great entry point for those clinging tightly to their snug baby tees.

The Baggy Sweater

While a loose, oversized sweater might feel like an obvious choice for winter, consider the look for cooler summer nights. Add some Ralph Lauren vibes to your day dress by throwing on a creamy knit and some beat-up cowboy boots. Or try the trend with something bright and trendy—perfect for chilly movie theaters and long car rides. The best part? The sweater turns into an around-the-neck accessory when you’re back in the sun. It’s a win-win situation.

The Baggy Popover

If you’ve already mastered the ex-prep oversized button-up, level up with its cousin: the baggy popover. A popover is essentially a button-up that only goes a third of the way, sort of like a rugby shirt. It’s just as easy to wear, if not a little cheekier. Popping the collar isn’t required, but it does keep the whole look from feeling a little too business casual. Pair the oversized look with your favorite slinky sandals and a tiny bag and you’re on your way to dinner.

The Baggy Long Sleeve

The ultimate skater boy uniform, the baggy long sleeve T-shirt is ideal for creating interest when it comes to straightforward separates. Suiting pants get a fresh upgrade and your favorite bike shorts feel new again. Stay on-theme by pairing the piece with sneakers you usually save for special occasions. Forgo tucking in the shirt to avoid bulkiness and instead embrace the cool silhouette. Lean in all the way with wide-leg pants.

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