How To Style Your Favorite Comfy Oversized T-Shirt

We all have one — that wildly cozy oversized t-shirt that seems to welcome us into the open arms of comfort, all while giving us an effortless mojo. Though many of us reserve wearing such a comfort piece strictly for within the borders of our own homes, we're happy to report that there are, in fact, a slew of ways to style your favorite comfy tee without sacrificing any of the cutting edge fashion that we prefer to don on the streets. 

The best part of styling an oversized t-shirt, arguably, might just be the fact of how versatile they are; they can be dressed up, dressed down, look chic and polished or edgy and loose, and can even be pretty sexy if paired with the right accessories.

What's more, fashion experts are weighing in on just how fun-yet-functional the oversized trend is proving to be. "We're seeing a return of '90s trends in general, and we really love to see the reemergence of hugely oversized pieces — they can be so fun to play with," Zadrian Smith, half of the stylist duo Zadrian + Sarah, tells Vogue. Smith notes that in order to properly rock the look, however, it's important to be mindful of how you style oversized pieces — going overboard can actually make it appear as if you're "drowning" in the clothing. 

Luckily, we're here to guide you through some of the best ways to rock that oversized comfy tee in your closet for an all-around relaxed, fashionable look.

Pair it with knee-high boots

Wearing oversized t-shirts as an ensemble is all about playing with silhouettes. When you pair the flow of the tee with a tighter look on the bottom, you're essentially creating the illusion of curve — something that can get lost with too many oversized pieces in one look. Knee or thigh-high boots are the perfect way to create this harmony, and Instagrammer Aki Ng shares an ideal example of the pairing.

Rock it with biker shorts and sneakers

Biker shorts mesh amazingly well with oversized t-shirts because their medium length couples with the longer length of the tee; they allow you to show some skin without getting carried away, and also provide some coverage for the thigh. Instagrammer Fabiana Justus decided to pair her plain white t-shirt with black biker shorts, a black belt, black and white sneakers, and a black blazer in order to create a stunningly minimalistic ensemble.

Accentuate it with a fanny pack

You don't have to be a leading fashion expert to know that accessories can make or break an outfit, and while we thought the fanny packs of the '80s and '90s were long dead and buried, they — like most things — made their official comeback in recent years. Fanny packs are no longer considered uncool or saved only for dorky dads; in fact, they can be seen on some of the top runway models of the 2020s, and @Emilyyluff of Instagram teaches us exactly how to pair one with an oversized tee.

Tuck it in for a '90s vibe

An oversized t-shirt tucked snuggly into a pair of vintage jeans is notably a pretty iconic look — it's the look that we imagine a '90s Cindy Crawford rocking on her day off while still appearing runway-ready. There's just something about this duo that screams "I don't care," and in the best way possible. Instagram content creator @Thecheekydna shows off her take on this pairing — we simply love how old-school and put together she makes this outfit appear.

Pair it with a large bag

Not only are oversized t-shirts in style, but oversized bags are as well. "Small bag fatigue is starting to settle in," celebrity stylist Thomas Christos Kikis tells Vogue. "People are out again and they have stuff! The Fendi Spy bag era is upon us, and I'm ready." Instagrammer Yesenia Soto marries the two trends beautifully with an all-black look.

Amplify the style with heels

Believe it or not, colors aren't the only thing that can provide contrast in an outfit — pieces can be opposing forces, too. Oversized t-shirts are a relaxed item of comfort, and what article of clothing is the sheer opposite of comfort? That's right, a high heel. Heels are our sexy, timeless friends that can elongate your legs to make you appear taller and slimmer, but anyone who's worn a pair for longer than a few hours knows the price of pain that comes with this. If you're feeling brave like Instagram fashion guru Ines Custodio, pair your tee with a bold set of heels for an elevated ensemble.

Play with dopamine dressing

Dopamine dressing took the 2022 fashion world by storm, and with all of the endless color possibilities t-shirts offer, playing with bright options can enhance your wardrobe even more. For example, if your favorite oversized tee is yellow, try amplifying it to the maximum potential with yellow bottoms. Or perhaps, like Instagrammer Preety, if you have a neutral colored t-shirt such as white, jazz up the whole look with a vivid pair of pants.

Balance the act with cargo pants

Sure, cargo pants are baggy, but they're not baggy to the extent of being too much — which is exactly why cargos are the perfect choice to wear with an oversized tee if tighter options aren't your thing. This is a combo that gives off an overall sporty look that's perfect for sporting events, concerts, or a night in with a special someone or friends. Instagram influencer Jasmine Alvarez is a gorgeous vision of comfort and style in her cargo and oversized t-shirt combination.

Don it as a dress

This styling option depends on exactly how oversized your t-shirt is and where your comfort level of length lies. If your tee is oversized to the point of a dress length that's comfortable for you, why not go down that route? This look really amps up the femininity of the t-shirt to a whole new level and to prove it, Instagrammer @Becciabey executes the concept perfectly in her oversized long sleeve t-shirt.

Knot it for a tighter fit

If you're in the mood for showing off your curves, an oversized tee probably isn't the first wardrobe piece that comes to mind. The good news is that with a simple front knot, you can hang on to comfort and let a little skin show at the same time. Instagram's @Tessiefromtheblock shares a great example of just how fantastic a tied t-shirt can look.

Harmonize it with bell bottoms

Because an oversized tee typically flares out at the bottom, matching it up with another piece that does the same thing can be a remarkable look. Of course, bell bottoms are the ultimate flare pants and they actually blend fabulously with an oversized shirt, as seen on Instagrammer @Riiiddhi_. She flawlessly creates a balanced look of minimalism with simple silhouettes and sleek patterns.

Make it edgy with leather accessories

It's no secret that leather can make just about any outfit look a million times sexier, and this fact is no different when it comes to oversized t-shirts; leather is chic, classic, and timeless — a stark contrast to the sporty oversized tee. @Becciabey shares a look on Instagram that completely nails the leather and t-shirt combo while making us want to run to our closets immediately to eye up some playful new pairings.

Layer it with jackets and flannels

Attempting to layer a bigger, more flowy piece may sound like a difficult task, but @Southernmadetees of Instagram shows us that it actually couldn't be any simpler. Start by tucking the shirt into your pants for a more fitted look. Then, layer a flannel, leather, or jean jacket overtop in order to create some depth. To really take the layered look to the next tier, try stacking jewelry like bracelets and necklaces to complete the outfit.

Tuck the bottom into your bra

This styling technique is very similar to the front knot method, but without the tied knot taking over as a focal point of the outfit. By loosely tucking the bottom of the oversized tee into the lower portion of your bra or bralette, just as Instagram's @Britainandbrooks does, you're able to still rock the oversized look while showing off your curves and skin. We absolutely love how casual-yet-flirty this ensemble looks.

Go for an overall relaxed look

Some days, we don't mind enduring uncomfortable moments for the sake of fashion, but other days, there's no way we're willing to put on something we're not absolutely fully relaxed in. But who says comfortable can't be cute? Certainly not Instagrammer @Yamini_alladi, who dons a dreamy pairing of an oversized t-shirt with a loose set of jogger jeans. "Paired basic [jogger jean] pants with an oversized t-shirt and knotted it up," she explains. "Added a sling bag, big hoops, and wrapped a printed scarf on the bun for that extra bling to complete the look."

Enhance it with leather pants

While leather accessories certainly ramp up any style with ease, leather pants can do all of that plus a lot more. Typically seen with more risqué choices on top, leather pants — when completed with a casual oversized tee — truly add cutting edge style to an outfit. Instagram fashion stylist Saira Padilla snags a picture of this sumptuous duo with her clothing line's brown leather pants and black oversized tee.

Polish it up with a blazer

Is there anything a blazer can't do in terms of fashion? They can make any outfit look polished and professional, they can snatch the waist for a more slender appearance, and they can even elevate self-confidence. While not the most common of pairings, an oversized t-shirt topped off with a chic blazer will actually scream style. Instagram blogger Shirin Gwalani writes, "It was difficult to use an oversized t-shirt for a polished look but love how it all came together."

Use contrasting colors

If you're down for an eye-catching look, combining contrasting colors is a great way to do so because stepping away from "matching" causes the eye to be drawn to separate pieces rather than an outfit as a whole. When you wear your oversized tee with an opposing color, you're essentially giving each article its own chance to shine – @ipshitakaul shares her interpretation of this on Instagram with a striking purple and green urban look.

Add a sexy touch with fishnets

Feeling sexy and daring? The answer to what you're craving may lie within a pair of fishnets. Fishnets have long been seen as a scandalous choice of clothing, but fortunately for us, their place in mainstream fashion is loosening up a bit. When worn under an oversized t-shirt, fishnets present themselves as the completion of a rocker-chic glam image. This look on Pinterest that features an oversized rock tee, wide fishnets, chunky heels, and aviators couldn't show off our idea of stunning any better.

Reach for that mini or midi skirt

Amidst highlighting the fact that older generations are mystified by Gen Z, The Washington Post reports that the controversial generation had a huge hand in the recent surge of fearlessness in fashion. Skirts have gotten shorter, blouses are cut lower, and lingerie is now considered outerwear. In light of these changes, don't be afraid to take the plunge and go for a naughtier look with a mini skirt. The oversized tee-slash-skirt combo is certainly an alluring one, and the styling combinations are limitless.