How to Style Oversized Shirts: 12 Chic Ways
Learning how to style oversized shirts opens up endless outfit possibilities. This wardrobe staple has evolved from boyfriend-borrowed basics to high-fashion statement pieces. As iconic designer Yves Saint Laurent famously said, 'I wish I had invented blue jeans...the most spectacular, practical, and unpretentious thing in the world.' The same could be said of the oversized shirt—endlessly versatile and effortlessly cool.
Why Oversized Shirts Are a Wardrobe Essential
According to Who What Wear, the oversized shirt trend shows no signs of slowing in 2026. Its appeal lies in the contrast it creates—oversized volume balanced with fitted or slim elements elsewhere.
12 Ways to Style Your Oversized Shirt
1. The French Tuck
Popularized by stylist Tan France on Queer Eye, the French tuck involves tucking just the front portion of your shirt into high-waisted pants. This creates a flattering silhouette while maintaining the relaxed oversized feel.
2. As a Dress
Belt an oversized shirt at the waist and wear it as a mini dress with knee-high boots or strappy heels. According to ELLE, this look works particularly well with crisp white or striped shirts.
3. Over a Slip Dress
Layer an unbuttoned oversized shirt over a satin slip dress for the perfect day-to-night transition. This styling trick adds edge to feminine pieces.
4. With Bike Shorts
An oversized button-down with bike shorts creates the model-off-duty aesthetic that remains popular in 2026. Add chunky sneakers and a crossbody bag.
5. Tied at the Waist
Tie the front hem in a knot at your waist over high-waisted jeans or a midi skirt. This creates a cropped effect while showing off your waistline.
6. Off-the-Shoulder
Unbutton partially and wear off one shoulder for an effortlessly sexy look. Harper's Bazaar suggests this styling for evening events paired with statement earrings.
7. Under a Sweater Vest
Layer a sweater vest over your oversized shirt for preppy-meets-relaxed styling. Let the collar and hem of the shirt show for dimension.
8. As a Beach Cover-Up
A white or blue striped oversized shirt makes the perfect beach-to-lunch cover-up. Button partially and roll the sleeves for relaxed vacation vibes.
9. With Tailored Trousers
Contrast the relaxed shirt with sharp, tailored trousers for a high-fashion look. Full tuck creates polished sophistication while maintaining the oversized silhouette.
10. Under a Corset
Layer a corset or structured belt over your oversized shirt for dramatic waist definition. This combines feminine structure with masculine volume.
11. With Leather Pants
Balance the soft drape of an oversized shirt with sleek leather or faux-leather pants. This creates the perfect blend of relaxed and edgy.
12. Layered Under Blazer
For office-appropriate styling, layer your oversized shirt under a fitted blazer. The contrast creates visual interest while maintaining professionalism.
FAQ: Oversized Shirt Styling
How oversized should an oversized shirt be?
Aim for 1-2 sizes up from your regular size. The shirt should skim your body without looking like you borrowed it from someone much larger.
What body type suits oversized shirts?
Every body type can wear oversized shirts—the key is creating balance. Pair with fitted bottoms to show your shape, or belt the waist to define your silhouette.
Discover Your Oversized Shirt Style
Looking for more oversized shirt outfit inspiration? LOOQS uses AI to help you discover styling ideas from real fashion bloggers. See how others style oversized shirts for your body type and aesthetic—try it free today.