How to Wear Women’s Boots: Your Style Guide

With so many different styles and trends in women’s boots, it can be difficult to know what to choose to suit both your personal style and the season. But help is at hand! From ankle boots to knee high boots, calf boots to shoe boots, we’ve got you covered.

Take a look at our style guide below to find out what types of boots are in fashion now, what never goes out of style and what boots you should wear with your favourite outfits, whether you’re dressing up or down.

What Women’s Boots Are in Style?

With fashion and trends changing so quickly, it can be difficult to keep up. However, broadly speaking boots can be broken down by leg height.

Let’s start with women's ankle boots. These are great for seasonal transitions as they can work all year round whether with bare legs and shorts for summer, or dresses and tights for winter. They’re a wardrobe staple, and were everywhere on the catwalks (and the streets) at London Fashion Week.

Flat ankle boots, particularly Chelsea boots, have been very popular over the last few years, and show no sign of going anywhere. Why would they when they’re so versatile? Flat ankle boots tend to be more casual so don’t really work for the workplace, but they’re a super stylish (and comfy!) option for weekends.

Patterned and jazzy ankle boots have also been all over the catwalks in recent seasons, with a huge variety of fabrics, colours and embellishments to choose from. But don’t keep them just for dressing up – team them with jeans or a dress to add a funky edge to your daytime outfit.

Calf boots are another favourite. Often a bit more casual, these are best teamed with skinny jeans, leggings, and more casual skirts and dresses. Calf boots can be slightly harder to style due to the fact that they create a line across the widest part of your lower leg, so it’s important to get proportions right.

Are tall boots still in style?

Knee-high women’s boots have been back in fashion for a while now and show all the signs of sticking around, particularly as they’re great for colder weather.

Especially with heels, these tend to look a bit smarter than their ankle and calf-high counterparts, so are great for work or for dressing up skinny jeans for a smart weekend outfit. For a 70s-inspired look, try pairing them with a midi-skirt that covers the tops of the boots, or for the classic 60s look, you can’t go wrong with a mini skirt teamed with chunky-heels and opaque tights. Shearling and faux-fur lined boots are super-stylish if it’s a more casual look you’re after.

Thigh-high and over-the-knee boots are also having a bit of a moment, with the likes of Rosie Huntington-Whiteley, Jessica Alba and Jennifer Lawrence all being spotted in them recently.

How To Wear Women’s Boots

So how do you wear all the different types of women’s boots?

The great news about boots is that you can find a pair that will go with anything, for any occasion. Whether you’re off for a walk in the countryside, out shopping for the day, heading out for a night on the town or giving a presentation at work, the right pair of boots can make you look and feel great. Here are our tips:

Wearing women’s boots with jeans

As jeans tend to be more casual, they are usually reserved for nights out and weekends (unless your office has a more casual dress code, as many now do!).

There are almost as many different styles of jeans as there are styles of boots, so matching them up can be tricky.

Boots and bootcut jeans

The name says it all – bootcut jeans were made for boots! Cut so they are fitted to the knee but then flare out slightly to accommodate a boot, bootcut jeans work particularly well with ankle boots. They should be worn over the top of the boot, not tucked in (to avoid any bagginess or bulges).

Bootcut jeans also tend to work better with heeled boots, as this stops the hems dragging on the floor and gives a more streamlined look. For an everyday look, try some black chunky heeled boots, or dress up bootcut jeans with pointed stiletto boots.

Boots and skinny jeans

Skinny jeans look great with most types of boots as they can be tucked into longer styles, but also fit well with ankle boots and shoe boots. Black skinny jeans look fab teamed with black boots as this creates a leg-lengthening effect. Whether biker boots, Chelsea boots, heels or flats, anything goes!

With other jeans, tan ankle boots can give a casual, boho-style look when teamed with paler denim.

For a more casual look, slouchy calf boots or ankle boots are hard to beat, when teamed with skinny jeans and for a smart, but still casual look, riding boots teamed with dark skinny jeans and a cosy jumper or short coat are classy and elegant.

Ladies boots to wear with skirts and dresses

Again, there are hundreds of different styles of skirts and dresses out there so how do you pair up the right boots with your outfit?

Ankle boots with skirts

Ankle boots look great with most skirts and dresses. Midi skirts teamed with heeled ankle boots are very on trend – try an ankle boot in a contrasting colour or fabric. For a more conservative look, how about a buckled or lace up women's boot with a pencil skirt and oversized jumper – perfect for shopping trips or catching up over coffee? Or why not try a heeled bootie and a skater skirt if you want to show off your legs?

Knee high boots and skirts

Skirts are great for showing off stylish knee-high boots. Flat knee high boots are ideal partners for casual dresses and tights (and are comfy and cosy for winter weekends), while heels are a bit smarter so can be worn with smarter skirts and dresses for the office.

Boots with coats and jackets

Sleek and timeless, trench coats look fantastic with ankle boots or knee-high boots. Opt for heeled ankle boots for a polished, office-ready outfit, or flat knee-high boots for a casual weekend look. Neutral-coloured boots like tan, black, or brown pair beautifully with classic beige or camel trench coats.

For a cosy, casual style, puffer jackets work well with flat ankle boots or calf boots. Pair with skinny jeans or leggings, a knitted jumper, and a scarf for an effortlessly warm outfit.

Biker boots or ankle boots add the perfect edge to leather jackets. Whether you’re wearing a mini skirt, skinny jeans, or a casual dress, the combination creates a chic, rock-inspired look.

Wool coats, whether long or cropped, are ideal with knee-high boots. Add a fitted jumper dress or skinny jeans and a turtleneck for a sophisticated winter look.

Wearing boots styling tips

Match boot height to your outfit: ankle boots with jeans or midi skirts, knee-high with fitted pants or skirts, over-the-knee with minis or skinny jeans.
Mix textures and colours: contrast suede with leather or pair neutral boots with statement outfits.
Layer and accessorise: boots complement coats, cardigans, tights, and accessories.
Consider the occasion: flats or low heels for casual looks, heeled or sleek boots for work or smart-casual outfits.

Some Ladies Boots FAQs

Here are some frequently asked questions about how to style women’s boots:

Can I wear boots to work?

Obviously this will depend on your workplace’s dress code (if it’s a very smart environment you’re probably better off sticking to traditional court shoes), but for the majority of offices boots are fine.

If your office tends to err on the smarter side of smart-casual, leather knee-high boots (with a heel) plus a smart skirt or dress will be fine. As will ankle boots and trousers. If your office is more casual, or you work in a creative environment, you’ll be able to play around a lot more with styles, colours and materials. Black lace-up ankle boots plus black tights and a day dress is always a good style recipe that works well for smart-casual.

However steer clear of over-the-knee boots, flat boots and more casual styles – these should be kept for outside of work.

Can I wear boots with a suit?

Yes and no. With skirt suits, boots are generally not worn, so if the weather’s cold, you may want to travel in boots, but take a pair of shoes to change into once you get to your destination.

With a trouser suit, however, you can get away with wearing boots, as long as they’re smart and ideally have a heel as this will create a much more streamlined look. You should avoid anything too casual, and steer clear of anything that’s wider in the leg as this will spoil the line of your trousers.

Shoe boots, and more fitted ankle boots are fine to wear with a suit.

How do I wear women’s Chelsea boots?

Chelsea boots are a great addition to any wardrobe and perfect for colder weather. Team them with skinny jeans (either worn normally or rolled up to show a bit of ankle), rolled-up boyfriend jeans or a cute skirt or dress and tights. Top off with a sweatshirt or cosy jumper and a chunky coat and you’ve got the perfect outfit for casual wintry days.

Find more info in our Chelsea boots ladies style guide.

How do I wear over the knee boots?

Over the knee (or OTK) boots need not be intimidating. And if you’re worried about the “Pretty Woman” look, don’t be. By teaming them with more casual outfits, you can tone down the sassiness of the style for everyday wear. Try skinny jeans with a chunky jumper, or a skirt, tights and long coat or cardi. They can also be teamed with midi skirts as a fashion forward alternative to tights.

The trick is to not show too much skin – no more than 5 inches above the tops of your boots is best.

Can I wear boots in summer?

Yes, absolutely – in fact they’re a festival staple (and not just wellies!). Tan ankle boots will look fresh and summery teamed with just about anything: shorts and a T-shirt, a pretty sundress and bare legs, jeans and a vest-top – the possibilities are endless! Tan is less heavy than black, so it’s a great alternative for summer months.

Boho-style is always popular in summer, so wearing a pretty sundress or skirt with cowboy or western-style boots is always a good option too!

Conclusion

When the weather changes, finding the right boots and outfits can be daunting, but the good thing is that there are so many different boots out there that you’re sure to find many styles that suit you. It’s always good to have a few pairs in your wardrobe to suit different occasions and outfits, and to allow you to experiment with what looks good together (there’s your excuse to buy more boots!).

If you’re still stuck for inspiration, there are plenty of street style bloggers and Instagram accounts you can follow to keep you up to date with the latest boot styles and how to wear them. And if you stick to classic styles (you can add a twist or two!) you’ll have the basis of more stylish looks than you can shake a stick at!