How to Style Oversized Shirts Like Hailey Bieber: 5 Trendy Looks That Will Dominate Summer 2025
If there’s one style that’s effortlessly cool, incredibly versatile, and still turning heads in 2025, it’s the oversized shirt. Whether you’re walking city streets or heading to brunch, oversized shirts have become the fashion-forward staple—and no one pulls it off quite like Hailey Bieber.
This season, fashionistas everywhere are taking cues from Hailey’s easy, polished looks—pairing oversized button-downs with everything from linen trousers to sleek skirts. If your closet is craving a dose of cool, oversized shirts are the investment piece you need right now.
So, how do you wear it without drowning in fabric? Let’s break down 5 trendy oversized shirt looks that blend comfort, elegance, and street-smart fashion—using real outfit ideas straight from Hailey Bieber's iconic styling playbook.
Look 1: The Classic Knot & Tuck Combo
There’s something universally flattering about a relaxed-fit shirt tied at the waist. Hailey Bieber was recently seen styling a breezy oversized botton Print shirt, loosely knotted at the front and paired with crisp tailored pants. This look screams “chic off-duty model.
How to Recreate It:
Choose a lightweight Premium oversized shirt with vertical stripes or soft neutral tones.
Unbutton the last two buttons and tie the ends in a low, effortless knot.
Tuck the back hem loosely into a pair of high-waisted linen trousers or pleated pants.
Roll the sleeves up just below the elbow for a laid-back yet intentional finish.
Pro Tip: Add simple accessories—a chunky gold watch or narrow sunglasses—to keep the vibe polished. Else you can check same shirt- here
Look 2: Tailored Contrast with a Fitted Bottom
To offset the volume of an oversized shirt, Hailey often keeps the rest of the outfit structured. Think oversized white shirt tucked into sleek cigarette pants or a body-hugging skirt. The result? A silhouette that’s modern, elegant, and ultra-feminine.
How to Recreate It:
Start with a crisp oversized white shirt—go for one with a stiffer collar and defined cuffs.
Tuck it fully into tailored black trousers or a midi pencil skirt.
Add heeled mules and a structured handbag for an instant upgrade.
Consider leaving a few top buttons undone and layering with delicate gold chains.
Pro Tip: Pop the collar slightly for a touch of Parisian confidence.
Look 3: Hailey’s Blazer-Over-Shirt Statement
It may sound counterintuitive to layer on more when you’re already wearing something oversized—but Hailey Bieber makes it work. One of her signature moves? Wearing a structured blazer over an oversized pattern shirt for that high-low balance.
How to Recreate It:
Pick a pastel or Marble miracle abstract oversized shirt as the base layer.
Add a fitted blazer in a complementary tone (camel, charcoal, or muted green are on-trend).
Leave the shirt tails peeking out under the blazer and push the sleeves up slightly.
Pair with slim denim, ankle boots, and a mini shoulder bag.
Pro Tip: You can also belt the shirt under the blazer to create a faux hourglass shape. You can check same shirt- here
Look 4: Summer Boho with a Maxi Skirt
Oversized shirts aren’t just city wear—they thrive in beach towns, resort settings, and lazy Sunday afternoons. Channel Hailey’s softer side by pairing your shirt with a breezy maxi skirt for the ultimate coastal boho aesthetic.
How to Recreate It:
Choose a flowy oversized shirt in earthy or pastel tones.
Wear it half-tucked or completely loose over a cotton or chiffon maxi skirt.
Sandals or espadrilles and a straw hat complete the look.
Add a slouchy tote bag and layered shell necklaces.
Pro Tip: For vacation vibes, leave a few top buttons undone and wear over a bralette or swim top. You can check our Earthwave relaxed fit shirt here.
Look 5: Evening Drama with Leather & Boots
Yes, oversized shirts can be sultry. Hailey proves that when styled right, a loose shirt becomes a dramatic evening piece. Add sharp contrasts like leather textures or statement boots to elevate the look from basic to bold.
How to Recreate It:
Go for a dark-colored oversized shirt—navy, black, or deep green.
Tuck it loosely into a leather mini skirt or coated jeans.
Choose pointed-toe boots or strappy heels.
Statement earrings and a slicked-back bun will complete the outfit.
Pro Tip: Unbutton the shirt strategically to highlight a bold necklace or bralette beneath. You can check our Sea Green Mosaic print shirt from our collection.
