Best Classic Boots with Midi Skirts to Look Incredible This Winter

Midi skirts have been a fashion staple for the past few years, and there are no signs that they will ever be out of style. They are versatile, flattering and chic outfit can be dressed up or down depending on the occasion. And what better way to complete the look than pairing boots with midi skirts?

But not just any boots–you need a pair of statement boots that is both comfortable and stylish. In this blog post, we will share our top picks for the comfortable boots to wear with midi skirts. Whether you are looking for something the dressy, casual look, or on trend we have got you covered. So grab your favourite midi skirt, and let’s get started!

Chelsea Boots With Midi Skirts 

Chunky Boots 1

Chelsea boots create a stylish combination when paired with midi skirts. Their sleek silhouette and low-top design create a classic look that pairs perfectly with any fabric, colour, or style midi skirt. The key is to balance the outfit by pairing a bright, bold skirt with neutral-coloured boots. Depending on your chosen accessories, this look can be dressed up or down, so it’s versatile enough to take you from day to night.

For an enhanced style, try adding a layer in a contrasting colour, like black Chelsea, with a crème dress and brown coat. Whatever your style, Chelsea boots and midi skirts are sure to make you look stylish and put together!

 Knee-High Boots With Midi Skirts 

Women with knee high white boots
Be brave with your colour scheme like these white boots

If you’re bored of wearing mini skirts with knee-high boots and what to achieve that whole look, why not try a midi skirt? Midi skirts are a great way to flaunt your shape without looking too flashy, and they can be dressed up or down depending on the occasion. Midi skirts offer more coverage than mini skirts, which is always appreciated in the colder months.

Whether you opt for bold buckles or sleek, patent leather styles, Chelsea boots with midi skirts offer an easy way to elevate your personality and style. Try pairing them with faux fur coats and cashmere sweaters for extra warmth on chilly days. There are varieties of knee-high boots brands, and one of them is Dream Pairs shoes. Dream Pairs sells comfortable and stylish knee-high boots in leather or suede materials at great prices. 

Over-The-Knee High Boots With Midi Skirts 

Over the knee boots with heels
Over the knee boots with heels

Over-the-knee high boots and midi skirts are the perfect combinations for a chic and sophisticated look. They can be dressed up with a long billowy blouse or dressed down with a casual sweater for an everyday look.

When outfits like this are paired with midi skirts, over-the-knee high boots can make an outfit look fun and flirty, which is perfect for a night out. Brown leather midi skirts, a blue knitted top, and brown over-the-knee boots are a great look. Try wearing colours like black, brown, grey, or navy blue when you pair the boots with your favourite midi.

Chunky Ankle Boots With Midi Skirts 

Girl with chunky boots and midi skirt
Feeling adventurous?

If you’re feeling adventurous, try pairing thigh-high boots with a midi skirt for a sultry night-time style. The longer hemline provides visual balance and makes the outfit look effortless. They are typically made from leather or suede and have a low or moderate heel. For a bolder take on the trend, opt for over-the-knee boots that hit just above the knee — it’s sure to turn heads!

Try matching ankle boots with black floral midi skirts and classic blouses for added drama. Finish off the look with a belt and carry a structured bag for that extra bit of spin and polished touch. And don’t forget about colour blocking – mix bright-coloured ankle boots with neutral-toned midi skirts for an eye-catching outfit that is sure to look amazing.

Cowboy Boots With Midi Skirts

Surprisingly elegant cowboy boots on a lady
Surprisingly elegant cowboy boots

Cowboy boots with midi skirts can look surprisingly elegant. For a more casual, boho-chic look, try an oversized denim or leather jacket with your boots and skirt. This is a great way to add some charisma to any outfit while still managing to express sophistication. If you’re feeling daring, wear suede-embellished western boots with knitted skirts for a fun night out.

Try pairing cowgirl boots with a floral midi skirt in the summer for a cool, stylish and cute way to wear cowboy boots. This look is not only fashionable but also ultra-feminine and very flattering. Just make sure to choose a skirt that hits at or below the knee, so your boots don’t get lost in the fabric. Trust us; this is one style trend you don’t want to miss out on!

Heeled Boots With Midi Skirts 

A classic look with a midi skirt
A classic look with a midi skirt

Pairing it with heeled boots is a great way to rock the midi skirt trend. Heeled boots with midi skirts are an elevated wardrobe staple that will always stay in style. The combination of the length and fit of the skirt and a heel gives you a long, lean silhouette that looks great for any occasion. Heeled boots make your legs look longer and give you an extra boost of confidence as you stride into any room.

Whether you’re wearing a pleated midi skirt or an A-line style, team it with a pair of block-heel boots for a polished finish, go for black or brown leather styles to create a sophisticated look, while suede pairs will give your outfit more of a boho feel.


Midi skirts are a key wardrobe item for fall, but finding the right footwear to go with them can be tricky. With so many choices on the market, deciding which pair of shoes is right for you can be difficult. But we’ve done the legwork and helped to explore for you and compiled a list of our favourite picks. From classic black ankle boots to on-trend over-the-knee styles, there’s something for everyone for all seasons. 

The next time you’re struggling to figure out what shoes to wear, try one of these comfortable boots with midi skirts. From ankle booties to knee-highs, there’s a perfect match of boot for every outfit. We’ve rounded up our favourite boots to wear with midi skirts, so all you have to do is shop!