What To Wear With Leggings - THE STYLE INSIDER

No woman’s wardrobe would be complete without a pair of simple black leggings. Although some people swear these comfy bottoms only belong in the gym, the revolution of ‘leggings as trousers’ has won many of us over. They’re flattering on every figure and are far more comfortable than jeans, plus they’re usually far more affordable. What’s not to love? You’d be surprised at how many looks you can create  with one pair of black leggings, as well as the many occasions that they work for. Say goodbye to sticking to the gym-only rule and get on board with the revolution with our complete guide of what to wear with leggings.



Leggings to work? As shocking as it may sound, it’s totally possible to wear them around the office and remain professional in appearance. The key is all in the styling, making sure you pair your comfy leggings with more formal pieces.

A longline shirt is flowy and breezy yet sophisticated enough to wear around the office. Make sure you choose a shirt that is longer in length than a regular fit as this will disguise the leggings and make them look more like trousers. Shirt dresses have been a hot trend in business wear, so don’t be afraid to go oversized with your choice.

Heeled boots are huge fashion favourite, especially when it comes to workwear as they’re often more comfortable than heels but just as stylish. Black oozes sleek sophistication and flatters every body type, which is why it looks so great with leggings. Match your black boots with an understated leather tote bag before throwing on a statement cardigan to complete the look.

Rob’s Top Tip: Cinch in your waist and add more shape to the outfit by wearing a belt around the middle of the shirt. It’ll transform any old shirt into a stylish dress as well as looking more shapely while remaining professional.



Many girls practically live in leggings in the winter, and who can blame them? Cosy and comfy yet fabulously flattering, they’ll keep you warm while showing off your legs effortlessly.

You’ll want to prioritise staying warm during the cold seasons, but that doesn’t mean you have to stick to bulky coats and gloomy colour palettes. Layering is key to a winter look that is as practical as it is trendy, offering the best of both worlds without the need to compromise. Start with a base of thick black leggings and a relaxed longline tee with long sleeves before layering a cosy cardigan on top to keep the cold at bay.

Monochrome outfits may be effortlessly elegant, but can look dreary in autumn and winter. The coat is where this outfit shines, so choose one that really pops to brighten the entire ensemble. Red, rust orange and emerald green felt pea coats are colorful yet classy, especially when you opt for a more muted shade rather than neon. Finish off the look with some chunky biker boots and a black bobble hat to stay super cosy no matter the weather.

Rob’s Top Tip: Relaxed fit tees are a comfortable wardrobe essential that can be worn again and again for a number of occasions, creating an understated look when paired with leggings. Having a supply of plain tops can really boost your wardrobe as you’ll have a solid base to work with. Plain white tee, leather jacket and leggings? Oversized black sweatshirt and leggings? The options are limitless with basic tops.



Leggings were practically made for lazy days and are often a go-to when it comes to comfortable fashion. Probably the easiest look of all is the classic all-black look, with a plain oversized hoodie under a unbuttoned fluffy coat resulting in a stylish contrast when paired with tight leggings.

Stray from the black when it comes to shoes by opting for a pair of fresh white trainers. This will make your outfit pop without straying from the minimalist feel. Sporty shoes are no longer meant purely for the gym and are the perfect addition of a pair of plain leggings. When it comes to accessories, keep things simple with a black crossbody bag and dainty earrings.

This look is simple yet chic, perfect for travelling or running errands.

Rob’s Top Tips: Dainty earrings and necklaces help to keep things elegant and classy, despite the understated dress code. Avoid chunky jewellery or purses when wearing all black unless you want a more edgy vibe.



Don’t fancy stepping out of your leggings for a first date? It’s totally possible to wear them for this occasion, so long as you style them with more formal pieces. Camis are the perfect choice for a date as they ooze flirtatious vibes without baring too much skin. Make your outfit one to remember by choosing a colourful top with pretty lace detailing.

Show your date that you’re a girl who can do both by pairing your girly cami with an edgy leather jacket. Get that second date in the bag by wearing some show stopping black heels with metallic detailing. The subtle gleam is sure to catch your date’s eye and you’ll feel on top of the world knowing you look good from head to toe.

Speaking of bags, clutches are a great option for a date. They’ll add class to the leggings and give you an opportunity to bring some sass to the look by choosing one that matches the colour of the cami.

Rob’s Top Tip: Wearing a belt is an easy way of making leggings look more like structured trousers, especially if it isa chunky buckle. Make sure it’s tight and doesn’t move around easily. It should sit precisely where belt loops would normally sit, so ensure it doesn’t hang down too low or high.



Looking for a dazzling party look, but still want the added comfort of leggings? Yes, you can have both. It may sound crazy, but wearing leggings under a button-up maxi dress can result in a high-end outfit worthy of the runway. Only button the dress halfway down so it flows around the leggings majestically, revealing a perfect combination of edgy fashion and pretty femininity.

Leggings over a dress may sound like something from an old-school red carpet, but the billowing nature of the look exudes striking glamour. Pair it with some sleek strappy heels and a matching clutch – tassel detailing is a fashion favourite when it comes to accessories, so stay on top of the trends by incorporating it into your look with the purse.

Rob’s Top Tip: Wearing black leggings underneath a flowing dress oozes modern sophistication, but those who want to take it one step further can experiment with colour. A flash of red under a black dress, for example, can really steal the show.