How to style leggings in winter

How to style leggings in winter

Amon Fearon - November 25, 2022

Not all leggings are created equal, and the right pair can become a mainstay in your winter wardrobe. But how do you style the best leggings in winter? We’ve put this guide together to point you in the right direction.

Here’s what we’ll cover:

  • Are leggings still in style?
  • What top to wear with leggings?
  • What shoes to wear with leggings?
  • How not to wear leggings

Let’s get to it.

Are leggings still in style?

Some people reject the idea of wearing leggings outside the gym but a pair of premium sports leggings lend themselves perfectly to daily use and, when accessorised properly, can be the basis of a stylish outfit.

Context is key. An outfit with leggings can work great for most occasions whether you’re out socialising in town, on a countryside walk, or going to yoga class. Only in more formal situations are they best avoided such as job interviews or events with strict dress codes. Dressing for comfort and ease of movement has become an important styling consideration, and as such, leggings remain a popular trend.

When wearing leggings out and about, here are some things to consider:

Will they be the main event?

Most people wear leggings instead of trousers rather than using them as underlayers. But switching out tights for leggings under a dress or skirt is a reliable way to keep yourself warmer in the winter, and in this situation they impact your overall style less.

When styling leggings, decide whether they’ll be the main event or whether you’ll be layering them underneath something else. This will influence other outfit decisions. When layering up for outdoor exercise in the cold weather, use base layers instead as they're specially designed for more warmth and protection.

How active do you want to look?

With leggings it’s easy to create a stylish outfit that looks like you’ve just left the gym, but you can also lean away from this aesthetic completely to achieve all sorts of looks. 

Make this decision early on as well, then build your style from there.

Will you be warm enough? 

Depending where you live, winter temperatures can be punishing. Some legging materials won’t be up to task, and will leave you with freezing legs any time you’re outside. 

Think carefully about your legging material and the temperatures it’ll need to stand up to. Fleece-lined/wool leggings made from thicker materials might be warm enough to wear as a single layer, but a lower-quality pair could have limited benefit.

Are you going for a pattern? 

The spectrum from solid colour to garish pattern is very wide, with lots of options in the interim. Solid black leggings are the golden standard as they're easy to match with most tops, hide sweat well, and give you more room to be creative elsewhere. However, patterned leggings make a bolder statement that draws attention towards the style rather than athletic fit. Busy patterns aren’t typical in sport and less likely to be designed for performance.

Your answer to this question will play a big role in determining what your overall style looks like.

What about transparency?

Some leggings are solid; others you can see through, whether in part or in total. When you’re styling leggings you can play with this to achieve some great looks, but you also need to check you’re not showing more than intended.

Will they perform?

There’s more to wearing leggings than style: good leggings are designed to perform. If you’re thinking about your style in the gym, choosing the right pair of gym leggings comes with its own considerations.

Below you’ll find a quick rundown of what you’re looking for when choosing gym leggings, and more comprehensive information is available in our dedicated guide.

  • Material: a lot of gym leggings are a Lycra blend, as the material gives comfort and stretch. Premium sportswear makers like Castore opt for a nylon and elastane blend as it’s incredibly soft and long-lasting.
  • Elastication: there’s nothing worse than loose leggings that slip down during a workout: choosing high-quality fibres and leggings that fit will help you avoid this situation.
  • Breathability: breathable fabrics allow air to pass through, helping to keep you cool during a workout. This is a crucial property for gym leggings and also good for summer months, so make sure to check your pair is breathable.
  • Wicking: moisture-wicking fabrics actively pull moisture through them, rather than just allowing air to passively pass through. This means they’ll pull sweat away from your skin to keep you cool and reduce chafing. Lower-quality brands may not use wicking materials so it’s worth double-checking.
  • Anti-odour properties: it’s unavoidable that working out sometimes leads to unsavoury smells, but certain materials are better than others at keeping you fresh. We recommend choosing anti-odour fabrics for gym leggings.
  • Pockets: this might sound trivial but in certain situations having pockets can make a big difference. If you want pockets, make sure to choose a pair that has them!

Castore womens black leggings

Now we’ve been through important considerations for styling leggings, let’s look at some specific garments you can wear with them.


What top to wear with leggings?

As we’ve established, there’s no reason why gym leggings should be confined to a gym environment, or be restricted to gym-friendly outfits. You can pair leggings with all sorts of tops, from a casual short-sleeved tee to a smart blazer or anything in between.

A t-shirt

A simple staple: throwing on a t-shirt with a pair of leggings gives a casual, versatile outfit that’s great for indoor environments in winter. They’ll more than likely be covered by outerwear but you’ll still want to colour coordinate to wear with an open top on milder days. Plain tees nicely balance out a loud, long coat. While seasonless trends are on the rise, winter clothes tend to be understated compared to other seasons. So, t-shirt designs are a neat way to make these types of outfits feel more distinguished.

A hoodie

Women's blue hoodie and leggings

Hoodies offer sublime comfort with easily accessible pockets and head cover to protect you against the elements. A monochrome fit with leggings gives a casual appearance for relaxing days but doubles up as a throw-on to stay stylish with little effort if you need to go out.

A well-fitted jumper

Choosing a jumper that hugs your figure creates another casual look with leggings, while also keeping you warm when you’re outdoors. Plain colours work well, but as with a tee you can also play with designs on the front of the sweater to liven up your look.

A sweater dress

Another variation on the jumper vibe is a sweater dress. This longer garment will cover your waistline and change the feel of the overall outfit, while keeping you snug. When accessorised with a nice belt and boots, this style provides the best of both worlds to keep you warm and allowing room to dress up with a more sophisticated look to attend winter events.

A loose, baggy sweater

Womens oversized sweater with black leggings

Wearing a looser long-sleeved sweater or jumper over leggings is a great choice if you’re after a cosy look and feel. Perfect for mild winter days or time spent indoors when it’s chilly outside.

If temperatures continue to plummet and you need to go out, you could opt for a knitted jumper instead. Wool is superior to cotton for trapping heat for these occasions but best avoided if you plan on staying active. Most knit colours complement solid black leggings but this may be trickier to coordinate with coloured and patterned styles.

A training jacket

 Womens black hybrid training jacket and leggings

To keep that athletic look going when you head outdoors in winter, a training jacket is a great combo. This maintains the casual, sporty look without getting too chilly. They are perfect for exercise and occasions when you don’t want to carry heavy outer layers around indoors, for example, while shopping. Alternatively, go for a fleece-lined jacket engineered for low-impact activities. If you need extra warmth you can always supplement this style with a gilet.

White zip up jacket with grey leggings

A leather jacket

Leather jackets are wardrobe classics for a reason: they’re fashionable, versatile, and distinctly stylish. And it’s definitely possible to match a leather jacket with leggings - just make sure to choose a colour that works, most often something dark like black, navy or dark grey.

A blazer

An unexpected blend of smart-casual. Leggings with a blazer is a bold look but it is one that can work. Whether it’s a long blazer that drops below the waistline, or a short blazer with the sleeves bunched up.


What shoes to wear with leggings?

With such a wide range of tops to style leggings with, it should be no surprise that you’ve got a lot of footwear choices as well. Here are some options.

Lace-up trainers

Probably the safest bet: casual, active and comfortable, just like the leggings they’re worn with. Combine these two with a tee or a jumper and you’ve got a casual outfit ready to go.

Trainers are a great way to add flair to your outfit, too. Playing with colour, style, brand and so on unlocks a huge range of variety.

Slip-on trainers

Pretty much the same as the above, but without visible laces. If you’re super attentive to your style, this distinction may make the finishing touch on your outfit.


These casual shoes have a lower topline and offer a subtle variation on trainers. The overall look isn’t too dissimilar, but you might prefer this if you’re going sockless.


A simple, non-controversial choice. A pair of flats will complement any pair of leggings nicely, and you can switch up the colour to change the feel of the outfit.

Ankle boots

Covering up the cuff changes how leggings look in an outfit, and ankle boots are a good way to do this. In winter this will keep you a bit warmer as well, as they’ll cover up potentially bare ankle skin and keep the cold air away.

Strappy wedges

Combining the two above into low-heeled shoes with straps lets you lean more heavily into the smart side of the smart-casual spectrum. The same temperature considerations apply - these shoes may be better for milder winter weather - but you may find these better for pairing with jackets and blazers.


How not to wear leggings

This guide demonstrates just how versatile leggings are. You can easily achieve a range of looks when building a winter style around leggings.

And while there are no strict rules, there are some tips we’d like to share for getting leggings looking their best.

  • Believe in your decision: putting together an outfit at home is one thing, but wearing it outside is something else entirely. Trust in the decision you’ve made about what to wear and carry that confidence with you for the rest of the day.
  • Avoid showing more than you want to: some leggings are designed to be more revealing than you realise, especially when you bend down or sweat. A premium pair of performance leggings can help deter potential problems.
  • Cover the waistband and the cuffs: this simple trick disguises the fact you’re wearing leggings at a casual glance if you don’t want to draw attention to them.
  • Consider the overall flow of the outfit: leggings are skin-tight, so tends to work better with something a little baggier on the top half if you’re not exercising.


Whether you’re heading to the gym or out into the city, leggings are a reliable and versatile outfit choice. Find the right pair and match it with the right clothes and you can achieve comfort, style, warmth and performance: the whole package.

Remember to consider the performance aspects of the leggings you choose as well as how they look. Premium brands will use higher quality materials to keep you warmer and make noticeable improvements to your performance.