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Fashion & Style

8 Ways to Style Oversized Shirts

by Jacky Lovato, Guest Writer

We love a skinny-cut, slimline, bodycon or curve-hugging silhouette, but there’s more than enough space in our wardrobes for this year’s ultimate fashion staple: loose and ultra-breezy oversized shirts.

This versatile, comfy must-have pairs perfectly with pretty much everything. So, whether you’re wondering how to style oversized shirts or what to wear underneath yours, we’ve got you covered!

Are oversized shirts in style right now?
In 2021, everyone from Hailey Bieber and Kendall Jenner to Gigi Hadid has shown that oversized can be just as stylish as something more fitted. If you’re ready to jump on the trend, shop for oversized items and not just bigger styles – purposefully oversized pieces are structured in all the right places. They can easily complement baggy bottoms or be paired with fitted items to balance out the look.

How to wear oversized shirts

Hailey Bieber wearing a white oversized shirt with denim shorts, trainers and sunglasses

1. With Denim Shorts

Denim shorts and an oversized shirt are the perfect casual combo in warm weather. Hailey Bieber shows us just how it’s done in a crisp white boyfriend shirt and denim shorts. This cool daytime look is casual and guarantees comfort when running errands, especially when paired with trainers.

2. For Back to Work

Oversized items can be dressed up or down effortlessly. If you’re looking for a smarter combo for the office, try a fitted white tee and tailored trousers with a crisp oversized shirt. Kendall Jenner wears minimal accessories to pull off the look, sticking to a slim black belt and strappy flat.

Kendall Jenner wearing a white oversized shirt with a white t-shirt cream trousers and sandals
Ashley Roberts wearing a green oversized shirt with red knee high boots

3. As a Dress

If you’re wondering how to wear an oversized shirt as a dress, Ashley Roberts has perfected the look. Whether you’re wearing a button-down or a tee, an oversized shirt can take you from casual to smart in the blink of an eye. Pair yours with a blazer and boots or keep it ultra-casual with an oversized tee, trainers and a few key accessories.

4. With Jeans

Elevate your ‘I’ve just rolled out of bed’ look with a relaxed and breezy oversized shirt, straight-leg jeans and flats. It’s comfy, cool and seriously effortless. Ashley Olsen keeps it simple with a few key accessories and a pair of sunglasses. Perfect for feeling cool but looking put-together as you’re out and about.

Ashley Olsen wearing a blue oversized shirt with blue jeans, sandals and sunglasses
Gigi Hadid wearing a blue oversized shirt with whit cycling shorts and sandals

5. With Cycling Shorts

Wondering how to style an oversized button-up shirt? Balance it with tighter-fitting bottoms like cycling shorts, leggings or a mini skirt. This combo gives ultimate laid-back vibes, but a bit of careful styling makes it all look very deliberate. Gigi Hadid looks fresh-faced in this cool off-the-shoulder shirt, minimal accessories and a stylish pair of sandals.

6. Belted

Cinch your oversized shirt dress at the waist to create a new silhouette. It’s an effortless go-to look for day or night. Keep it casual on a dress-down day with rolled-up sleeves and trainers, like Emily Ratajkowski, or dress it up with a floppy hat and a large tote bag.

Emily Ratajkowski wearing a white oversized shirt with a brown belt and white trainers
Ashley Roberts wearing a oversized shirt with a vest and knee high white boots

7. Layered with a Vest

There are more than a few ways to wear an oversized shirt as a dress, and layering adds a whole new vibe to the style. A shirt dress looks stunning under a vests and gives you the chance to play with different necklines and layer lengths. Ashley Roberts accessorises this smart combo with knee-high white boots and gold necklaces.

8. Buttoned and Breezy

Cool satin fabrics in oversized styles are the perfect combo for summer. Candice Swanepoel looked relaxed and chic in this breezy button front with spread collar, pairing her printed co-ords with simple white sandals and oversized sunglasses. And just because your look is baggy, it doesn’t mean you can’t show some skin.

Candice Swanepoel wearing a satin oversized shirt co-ord set and sandals