Take Oversized Outfits from Frumpy to Fantastic: 10 Expert Tips

We’re not gonna lie – the idea of wearing oversized anything absolutely terrifies us. The oversized trend in fashion is everywhere, and we’ve been trying to dodge it but it won’t go away! So we turned to our fashion and style expert for advice on how to embrace this look without cringing when we catch a glance of ourselves in the mirror. Here are the expert tips some of us need to make the oversized fashion trend work for us, including blazers, shirts, and pants. Keep hope alive, dear reader – help is on the way.

Our ultimate fashion guide on how to style the oversized trend

Oversized clothing is having a major fashion moment and we are totally here for it. Those billowing shirts, slouchy blazers, and baggy pants are the comfiest route to achieving a chill, off-duty look. But for those of us (most of us!) who don’t look like runway models, you may be convinced that a boxy fit will make you look too sloppy or larger than you are.

We’re here to change your mind. Oversized fits not only reframe your body but they can also reframe the way you think about your body. Think of it like the ugly shoe trends: dad sneakers, Birks and clompy sandals, that have now become ubiquitous. Is it objectively flattering? Not really. But does it matter? No, because the something’s off quality about an ugly shoe makes it interesting and gives you a cool factor.

An oversized proportion works in the same way in that it goes against what is considered traditionally flattering (read: what is considered attractive to the male gaze). No obvious displays of cleavage, waist, or backside automatically leans to a more androgynous look. Think of the enduring and cooler than thou appeal of Katherine Hepburn, Tilda Swinton, Kristen Stewart and Cara Delevigne. We’re not saying you shouldn’t wear a body con dress ever again — just that you can and should break out of the narrow confines of traditionally flattering dressing every now and then. We’re willing to bet that you’ll like the way you look, move, and feel.

Ahead we have all the tips and tricks to pull off the oversized look in an intentional way.

How to style an oversized shirt

Now is the perfect time to dig out your ex’s button down from the back of your closet and experiment. The excess fabric is perfect for getting a custom fit that’s right for you.

1. Don’t feel like you have to use all the buttons. Get that slightly undone look by leaving the bottom buttons open and flowing.
2. Alternatively, you can treat the shirt like a loose open jacket or just buttoned on the bottom so it’s falling off the shoulder. Pair with a tank or crop top underneath.
3. Vary the hem and create dimension with a French tuck. That’s a fancy way of saying tuck the shirt loosely in the front and leave it untucked in the back. Or knot it in the front for more waist definition.
4. As we head into the warmer months, it’s easy to balance the top heavy look of an oversized shirt with a more bare look on the bottom. Pair with biker shorts or a mini skirt and show off those legs.
5. Footwear is key. To pull this look together in a polished way, you’ll want to forego the sneakers and choose an elegant mule or strappy sandal.

How to style an oversized blazer

A loose, boxy blazer is one of our wardrobe heroes. It’s put-together but doesn’t take itself too seriously. In the warmer months, just switch to linen to get the same cool look without overheating.

1. Pick your favorite color and go monochrome. From H&M to Khaite, all the blazer styles have matching trousers or shorts. It could not get more chic and easy.
2. Accessorize with a belt — either over the blazer to create an hourglass shape or with your jeans of choice to create more subtle definition.
3. To avoid the blazer overwhelming your frame, play with proportions. A fitted top will balance the bulkiness of the jacket if you’re pairing it with wide leg trousers or baggy jeans. But if you’re wearing an oversized shirt or tee under the blazer, go for shorts or a mini skirt.
4. Roll up the sleeves. Cuff your pants. Revealing some skin keeps the overall outfit from looking too heavy.
5. Keep the jewelry on the minimal side. You don’t want to weigh down the excess fabric of the blazer with more stuff.

How to style oversized pants

Super slouchy pants are arguably the toughest to get right but we think it’s worth it because their comfort level is off the charts.

1. Pick a high-waist silhouette to get that elongated line. Even better, check for multiple front pleats; they are tailor-made for some give and to provide that graceful, fluid fit.
2. To get the most drapey and flowy look, go for lightweight fabrics like cotton or linen and blends with Tencel Lyocell, ramie, rayon, or elastane.
3. Black will always be a chic and versatile choice but consider a statement color to make styling a breeze. The pants become the focal point and you can simply pair it with a basic white t-shirt of black tank top.
4. Your instincts are correct that a slim-fitting or crop top would look the most proportional with slouchy pants. A little skin reveal helps break up all the excess fabric.
5. When it comes to footwear, keep it light. Think thong or strappy sandals so that your bottom half doesn’t look too heavy. We’re going for a floating (not drowning) effect!

Need a few essentials to get started? We got you.

1. Wardrobe.NYC

Start with WARDROBE.NYC‘s oversized cotton shirt with a curved hem made for expert tucking.

BUY NOW – $400.00.

2. Remain Blazer

This Remain blazer is the perfect transitional weather piece made in naturally breathable linen and in a warm white that goes with everything.

BUY NOW – $355.00.

3. Cos Trousers

Your statement trousers are here; you just gotta go for it. Cos delivers with this wide leg style made from linen in the trending hot pink color of the season.

BUY NOW – $135.00.

4. Girlfriend Collective

Consider this crop top and biker short combo from Girlfriend Collective your go-to underpinning when rocking the oversized look.

BUY NOW – $46.00 for top.

BUY NOW ($48.00 for bottoms.

5. Alexander McQueen

A sleek, pointed mule is key to making the oversized look polished and elegant. This Alexander McQueen style is rendered in mirrored leather with a chunky chain.

BUY NOW – $1,090.00

6. Kinn Studio

This layered necklace from Kinn Studio adds a little character but keeps it light to balance out the exaggerated proportions.

BUY NOW– $880.00.

Our ultimate guide on how to style the oversized fashion trend

There you have it — all the tricks of the trade and basic essentials you need to make the oversized trend your own. Using these expert style tips, anyone can wear the oversized fashion trend, including blazers, shirts, and pants, while feeling confident and chic.