September 15, 2026 A Closet Classic, Styled Your Way
Some pieces earn their place in a closet by looking better every time you return to them. The boyfriend shirt is one of those rare finds. It’s relaxed without feeling sloppy, familiar without becoming boring, and ready to shift with the season.
How to Style It
Start with the classic combination of an oversized button-down and straight-leg denim. Leave a few buttons open at the collar and waist, loosely tuck one side, and add loafers or flats. The roomy proportions give the outfit character, while structured denim keeps the shape balanced. For cooler days, layer a fitted turtleneck underneath and roll the cuffs so both fabrics show.
If you prefer a softer look, wear the shirt tucked into a midi skirt. It creates a nice contrast between crisp cotton and fluid fabric. Finish with your favorite flats for daytime, then switch to ankle boots and a small shoulder bag for dinner.
The same shirt can also work as a mini dress. Add an oversized blazer and belt the look for an outfit that’s fun and unexpected.
Pay attention to fit when shopping. Look for dropped shoulders, sleeves that can be rolled comfortably, and enough length to wear tucked or loose. The fabric should have some movement but still hold the collar’s shape. If the shirt feels too large, define your waist by tying another shirt around it.
What makes the boyfriend shirt a classic is its ability to move between moods. It can look casual, tailored, romantic, or slightly undone depending on what surrounds it. Trends may change the preferred stripe, cuff, or silhouette, but the central idea remains: a borrowed-from-the-boys button-down makes getting dressed more interesting. It is the kind of closet staple that invites experimentation and keeps proving its worth, season after season, without asking for much fuss.
Find your favorite version on the racks of your neighborhood Crossroads store.
