7 Ways to Wear Oversized Shirts

Once a preppy classic, now an effortless go-to, oversized shirts are having a major moment. While typically associated with fall closets, they’ve since been upgraded to the ultimate transitional piece, taking you from summer evening cover-ups to early fall days. Perfect with everything from boxer shorts and minidresses to baggy jeans, the overall effect—when styled the right way—is one of casual cool. Wondering how to wear them? From the boardroom to brunch, read on and discover 7 fresh, crisp ways to style oversized shirts right now. Spoiler alert: it’s all about a carefree untucked look.

1. Achieve All-Over Denim with Baggy Jeans

Cooler than a denim jacket, oversized shirts cut from the chicest denim have a similar effect, but with a fresh, modern ease. To really nail this supersized look, wear unbuttoned over a tank and pair it with baggy jeans and heels.

2. Invest in an Oversized Shirtdress

Ready to consider an XXL dress? Whether pinstripe or denim, this easy look borrows from the oversize shirt trend and takes it one step further. Perfect for late summer days at the office or when the occasion calls for polished low-key effort, it looks as good with sneakers and western boots as your favorite pair of sandals.

3. Make A Statement with Boxer Shorts

If you saw our piece on late summer trends, you’ll know everyone’s buying boxer shorts right now. The best way to wear them? With an oversized shirt, of course. Match up your blue hues for the coolest twist on boardroom basics—but this look is best kept for OOO.

4. Consider It Your Ultimate Layering Piece

When it’s too warm for a sweater but too cool for bare shoulders, consider throwing on an oversized shirt as the perfect light layer. Tossed over a minidress or worn unbuttoned over a bralette with wide-leg pants, an oversized shirt makes transitional dressing easy.

5. Your New Vacation Essential

If you have a weekend getaway or a sun-soaked vacation planned, be sure to pack an oversized shirt. Slip yours over a swimsuit or bikini instead of a sarong or caftan for a modern take on a classic cover-up. Linen or cotton, there are a plethora of breathable oversized shirt options you won’t want to leave home without.

6. Include One in Your Workout Getup

Whether a gym or Pilates session is more your speed, don’t overlook an oversized shirt as part of your athleisure routine. Worn over a sports bra, leggings and sneakers or a simple tee and bike shorts, it’s a cool girl go. Plus, mixing office and sports references adds a playful twist.

7. It’s Intrinsic to French Girl Chic

The simplest ideas are often the best and when it comes to achieving French Girl style, an oversized shirt is key. It’s the finishing touch to straight-leg jeans and a slick pair of loafers. Don’t forget your signet ring, either.