Learning how to style oversized t-shirts will add infinite versatility to your wardrobe. A simple and comfortable staple, knowing how to wear it to suit your personal style is key to sartorial success.
No capsule wardrobe is complete without a collection of oversized t-shirts, but they don't just have to be reserved for lazy days at home or sweaty gym sessions. One of the easiest items to dress up or down for every season, this style essential has endless styling possibilities. From cropped boxy fits to longer tunic shapes, how oversized you go is up to you.
Pair with relaxed fabrics like jersey and denim for off-duty days, or elevate your look with pieces like luxe leather pants, silk slip skirts, and a strappy heel for more formal occasions. For a more in depth guide on how to style oversized t-shirts, you can't go wrong with these foolproof outfit formulas that will reframe how you view this slouchy wardrobe basic.
1. How to style oversized t-shirts with a blazer
When it comes to how to style a blazer with an oversized t-shirt, the sharp cut, structured shoulders, and longline length of a classic blazer will make even the baggiest of oversized t-shirts feel smarter. To avoid overwhelming your frame, it’s best to keep your blazer true to size, as long as there’s enough room for your t-shirt to sit comfortably beneath it without ruching the sleeves or adding unwanted volume at the shoulders.
Robing (wearing your blazer over your shoulders like a cape instead of putting your arms through the sleeves) is a chic way to style a blazer if you find your t-shirt is too oversized for straightforward layering. When opting for a colourful or patterned blazer, choose a t-shirt in the same hue, or, keep it simple and chic with black or white version beneath to effortlessly channel the rich mom trend.
RRP: £32.99 / $40.99 | Neutral creige is one of the big fashion colour trends 2023 and this blazer nails the look. With just the right amount of room to layer over a baggy tee, it can be worn open with jeans and ballet flats for an office-ready ensemble.
RRP: £125 / $165 | This t-shirt has a slighty slouchy fit, but we recommend sizing up to get a true oversized look. Ganni tees are all the rage this year, so get ahead of the trends with this latest launch. Pair with white linen trousers on sunny days or denim shorts and sandals on holiday.
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RRP: $219 / £139 | Struggling with how to style leather pants? Leggings are a great way to experiment with the tougher fabrication. The streamlined shape is ideal for learning how to style oversized t-shirts as they stop your frame from being swamped.
2. How to style oversized t-shirts with boots
The category of boots is pretty broad, with a vast number of designs coming under the same fashion umbrella. Your boots could be a directional stompy pair of Doc Martens, an elegant knee-high iteration with a pointed toe and a block heel, or even a pair of cowboy boots to channel the shoe trends 2023.
The kind of boots you choose to pair with your oversized t-shirt will depend on the overall feel of your look, the length of your t-shirt and your signature style. Offset oversized t-shirts and chunky boots with a slinky slip skirt, or double-down with straight-leg dark wash jeans. If you're looking to wear your oversized t-shirt as a dress but don't want to have a lot of leg on show, try a pair of the best knee-high boots or over-the-knee boots to add extra coverage.
RRP: £25 / $39 | This Cos t-shirt has the ideal loose fit for styling with tighter bottoms or wide leg trousers for a casually cool finish. It is slightly shorter than most oversized tees, so sizing up is recommended if you prefer a longline cut.
RRP: £79 / $140 | Adding a dressed-up feel to the oversized t-shirt, a bias cut midi skirt makes for a flattering fit. This ditsy spotted pattern adds some texture to your look without being too bold, and it will pair perfectly with a range of hues.
RRP: $170 / £159 | Dr Martens boots have seen a resurgence in popularity in the last few seasons, mainly thanks to the return of 90s fashion trends. This lace-up style offers a tougher finish to skirt and dress outfits and are practical for every day.
3. How to style over-sized t-shirts with shorts
Fashion’s love affair with the '80s and '90s was one of the big fashion trends 2022 and shows no signs of waning, keeping oversized t-shirts and cycling shorts very much on-trend.
“A chic way to wear an oversized t-shirt is with tight cycling shorts, ankle socks, and trainers,” comments Farrah. “Princess Diana rocked this look and it remains on trend today. The key to this outfit is balance, and the oversized t-shirt works in perfect partnership with a tighter garment on the bottom half to balance out the silhouette.”
That's not to say form-fitting shorts are a necessary requirement. There's plenty of potential for tailored, utility, and longline city shorts too. To keep the balance, choose a style with a nipped-in waist, or colour block with a darker shade on either your top or bottom half.
RRP: £12.99 / $19.90 | When we think of the perfect oversized t-shirt, this is what we think of. Loose and comfortable but with some edge, you will wear this day after day - particularly when implementing a capsule wardrobe for travel.
RRP: £125 / $215 | Cargo shorts are right on trend for this season and they make a brilliant base for summer outfit ideas. Add a chunky belt and tuck your oversized t-shirt in to the waistband for a comfortable yet trendy finish.
4. How to style oversized t-shirts with jeans
If two pieces were to form a sartorial sisterhood, it would be oversized t-shirts and jeans. The fabrics work perfectly together for an effortless and relaxed feel. But that’s not to say this look can’t cut it for evening or smarter occasions too - you just need to consider the colour, fabrication and silhouette of both pieces and select the right type of jeans.
For daytime, go as oversized as you like with your t-shirt, rolling up the sleeves to exaggerate the effect, and team with the best wide-leg jeans or boyfriend jeans in mid to light washes (think stone blue through to white).
When it comes to how to style oversized t-shirts for the evening, on the other hand, this requires a slightly more structured silhouette and darker tones. Ideally, your t-shirt should be more subtly oversized (think one or two sizes up from your regular size) rather than all-out baggy. Looking for silk jersey fabrics for added luxe and tuck your oversized tee into tapered straight jeans or your best skinny jeans in black or indigo and finish with a pair of on-trend heeled mules.
RRP: £28 / $30 | The khaki green colour of this V-neck makes it an ideal transitional piece as we head towards fall. Contrasting with lighter denim washes whilst keeping a refined finish, you this affordable and sustainably made piece will last you years.
RRP: $248 / £329 | Straight-leg jeans are the ideal shape to complement an oversized t-shirt, preventing your outfit from overwhelming your frame, but often offering a more gentle balance than skin-tight iterations. The ankle-skimming hemline will lengthen legs too.
RRP: $79.99 / £49.99 | With a similar style to some of the best designer bags but for a more wallet-friendly price, this spacious shopper tote can do it all. Finish off your look with some chunky trainers or boots to tie your outfit together.
5. How to style oversized t-shirts with trousers
We’ve fallen hard for the wide-leg trouser trend, but choosing what to wear with wide leg pants can prove tricky. The best shirts can feel too formal, and a billowing blouse too fussy, but have you tried learning how to style oversized t-shirts with a pair?
For the whole look to work in synergy, select a t-shirt in the same hue as your trousers, or, if they’re patterned, pick just one colour out from within the print, or opt for a neutral hue to tone the look down. How oversized you can go with your t-shirt is dependent on the fabric of your trousers.
If they’re lightweight, with enough swish and movement to allow them to allude to the shape of your legs when you walk, you can get away with a long-line t-shirt, worn loose over the waistband of your trouser. Alternatively, if the fabric of your pants is starchy or structured, a cropped or shorter t-shirt is best to help you regain your shape by giving a flash of your waistband to nip you in.
RRP: £12 / $21 | The relaxed feel of this t-shirt pairs beautifully with a more structured and tailored trouser to give your look some balance. Pair with high-waisted silhouettes and do a French tuck for a chic finish, accessorising with a belt.
RRP: £85 / $129 | Keep it tonal with a similarly earthy-hued pair of trousers. The creased front helps to add structure to the wide leg and will elongate your silhouette in the process, drawing the eye up your frame.
RRP: $160 / £125 | Birkenstocks have seen a serious revival this season and we're not mad about it. Lean into the casual and relaxed feel that an oversized silhouette evokes by pairing your look with comfortable flats.
6. How to style oversized t-shirts with skirts
Want to add a cooler edge to a pretty skirt? An oversized t-shirt grounds a skirt look, making them feel slightly more androgynous in the process. For the most flattering fit, make your skirt a high-waisted one. Anything with a low or drop waist will not only make tucking your t-shirt in tricky, but also means you lose definition around your middle. To make this look work you'll want the kind of oversized t-shirt that says you've sized up once or twice, rather than going for something overly baggy, it should feel gently relaxed.
This look is also ideal for what to wear in the heat, as you'll get greater airflow to your skin in an oversized t-shirt. Not sure what colour t-shirt to wear with a printed or colour-pop skirt? You can’t go wrong with a classic neutral such as the best white t-shirts or a basic, plain black design.
“In terms of colour, I always suggest that my clients have an oversized white t-shirt in their wardrobes,” says Farrah. “It will go with everything, from midi skirts to jeans, and can easily be dressed up with chunky gold jewelry and a slick of lipstick.”
RRP: £14.90 / $19.90 | Uniqlo is unrivaled when it comes to great value basics, and this boxy white tee is a cheap and cheerful staple. The perfect shape for both comfort and style, we will be wearing this all summer.
RRP: £195 / $265 | Wondering what to wear in the heat on a busy city break? A flowy denim skirt is always the answer. With a loose fit and romantic broderie trims, this will stand out from the crowd without being too statement.
RRP: £139 / $269 | Tie your whole look together with these sophisticated and comfortable white mules. Accessorise with a stylish sun hat on holiday or a chunky gold necklace for evening dinner dates.
7. How to style oversized t-shirts with trainers
Fully embrace the sporty feel of an oversized t-shirt by teaming yours with trainers - all you need to do is pick a side. The fashion industry is currently divided into two teams when it comes to trainers: sleek and streamlined, or super chunky. The former works best with long trousers, while the latter works well with anything that finishes mid-calf or above, such as the best midi dresses.
Both styles of trainers are not only extremely practical, making hot-footing around town an all-around comfortable experience, but will keep your oversized t-shirt look feeling suitably relaxed. One of the easiest holiday outfit ideas for any destination, this is an outfit formula you'll turn to over and over again.
RRP: £15 / $18 | The low-key abstract design sets this apart from plainer t-shirts without stealing too much focus. The white base, teamed with lighter colours means this will go with multiple looks.
RRP: £15 / $25.99 | Soft fabric? Tick. Elasticated waist? Tick. Practical pockets? Tick. In one of this season's hottest hues, these shorts have Barbiecore nailed in one simple step.