The Art of the Oversized Tee: 5 Chic Ways to Style - TRESSNY

The Art of the Oversized Tee: 5 Chic Ways to Style

Gone are the days when an oversized t-shirt was reserved for sleepovers or lazy Sundays on the couch. In 2025, the oversized tee is the undisputed champion of "cool girl" style. It is the ultimate hybrid of comfort and chic—if you know how to style it.

Whether you are rocking a vintage-inspired graphic tee or a crisp, minimal solid, the difference between looking "effortlessly messy" and just "messy" comes down to styling.

Ready to elevate your everyday look? Here are 5 foolproof ways to style the oversized tees from our latest collection.

1. The "Princess Di" Off-Duty Look

This is the holy grail of athleisure. Inspired by the late Princess Diana’s iconic gym looks, this style is perfect for running errands, grabbing coffee, or travel days.

The Bottoms: Pair your tee with black biker shorts. The tightness of the shorts balances the volume of the shirt.

The Shoes: Essential here are chunky dad sneakers with mid-calf crew socks (scrunched down slightly).

The Accessories: A baseball cap and a structured tote bag.

Style Tip: If your tee is long enough, let it hang loose over the shorts. If you want more leg definition, do a slight front tuck.

2. The French Tuck & Denim

The "French Tuck" (tucking in just the very front of your shirt while leaving the back loose) is the secret weapon for oversized fits. It defines your waistline without losing the relaxed vibe of the shirt.

The Bottoms: This works best with straight-leg jeans or mom jeans. Avoid super skinny jeans with this look to keep the silhouette modern.

The Layer: Throw a blazer over your shoulders to instantly take this look from casual to "brunch-ready."

The Vibe: Classic, timeless, and put-together.

3. The "Dress" Illusion

If you buy your tees truly oversized (or go up 2-3 sizes), you can ditch the pants entirely. The T-shirt dress look is edgy and provocative but requires specific styling to ensure it looks intentional.

The Secret: Always wear hidden safety shorts underneath!

The Shoes: This look demands a heavy boot. Think Dr. Martens, combat boots, or knee-high leather boots. The heavy shoe anchors the look so you don't look top-heavy.

The Waist: If you feel like you’re drowning in fabric, cinch the waist with a corset belt or a chain belt for some edge

4. Knot It Up

Want to wear your oversized tee with a maxi skirt or high-waisted trousers? You need to shorten the hemline. Rather than cutting the shirt, use the knot technique.

How to do it:

Gather the extra fabric at the hem to one side or the center.

1.Twist the fabric until it creates a spiral.

2.Wrap it around your fingers to create a knot and pull the end through.

3.Alternatively, use a clear elastic band to tie the fabric inside the shirt and flip it under for a "cropped" look without the knot showing.

This pairs beautifully with satin midi skirts for a mix of textures (soft cotton vs. sleek satin)

5. The Professional Edge

Can you wear a graphic tee to work? In a creative office, absolutely. The key is juxtaposition—pairing the casual tee with strictly formal pieces.

The Formula: Oversized Tee + Wide Leg Trousers + Pointed Heels.

The Fit: Tuck the t-shirt all the way in tightly to ensure it lays flat against your body, then belt the trousers.

The result: A silhouette that says you mean business, but you’re fun to work with.

A Note on Sizing

When shopping our collection, keep in mind how you want the tee to fit:

True to Size: Will give you a relaxed fit (our tees are cut to be roomy!).

One Size Up: Perfect for the "French Tuck" or biker short look.

Two Sizes Up: Ideal for the T-shirt dress look.

 

Ready to find your new favorite fit?

Don't settle for stiff, uncomfortable shirts. Browse our New Arrivals to find the softest, most versatile oversized tees that you'll never want to take off

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