Boot Styling Guide

Your ultimate boot styling guide: how to wear all styles of boots this season

Here is your ultimate guide to styling all types of boots this winter season, from stunning knee-high boots to your trusty casual pair. We share plenty of styling inspiration, explore key looks for the season and show you how to transform your style from casual to dressy.

How to style Knee-high Boots

Knee-high boots are back with a vengeance this season. They have the advantage of lengthening your silhouette and look great with anything, including skinny jeans, skirts and knit dresses.  Here are some key looks to inspire your wardrobe this winter:

 Lunch with the girls

style knee high boots

When catching up with your favorite girls this festive season, you want to bring an element of classic sophistication with a contemporary twist.  The classic double-breasted trench brings the air of sophistication while the pleated skirt, in a fresh print, provides a fashion-forward twist. The stunning quilted detailing on these Sandringham knee-high boots also makes a confident statement.  Knee-high boots work well with mid-length skirts, but don't be afraid to also try them with a shorter skirt and layer tinted tights underneath.

Day at the cinema

How to wear knee high boots

For a casual and relaxed look, pair your knee-high boots with skinny faded denim. Make sure you choose knee-high boots with hidden flexible inserts, that easily allow you to tuck your favorite pair of jeans inside and still walk comfortably. Add a chunky textured knit in a statement color and layer with a bold printed scarf.  Pair with an unstructured tote or hobo bag for an effortless vibe.  Keep your makeup dewy and minimal.

How to wear Ankle Boots

I find every season what is considered “trendy”, in terms of boot length, varies dramatically.  It can vary from above the knee, killer boots one year to ultra-low ankle boots the following year. I love experimenting with different looks and boot lengths every season. However, regardless of current trends, I find I also religiously purchase a pair of high-quality black ankle boots every year, without fail.  This is because I find ankle boots super versatile. They are perfect for wearing with jeans for a casual look, as part of your trusty work ensemble and can be dressed up for holiday parties and flirty functions. Here are some tips for transforming your ankle boots from smart casual to party goddess:

Strolling downtown

Smart casual ankle boot outfit

For a smart-casual look pair your ankle boots with a pair of dark, skinny jeans. Wear with a delicate 100% merino wool roll-neck sweater. Make it pop with a stunning statement coat in rich, deep tones like forest green or wine red. Add interest by finishing off with embellished accessories.  The studded elements on these Dallas Boots add a touch of luxe to your outfit. You can also incorporate studded detailing in handbags and other accessories to bring it all together.  Opt for natural makeup, with a rich lip color.

NYE Party

How to wear ankle boots to party Ankle boots will serve you well leading up to the party season. They look stunning with a pair of leather or coated denim jeans.  Have fun incorporating a lurex top or tunic, to add an element of sparkle to your evening. Shimmering fabrics are bang on trend and will help you get into the party spirit. If opting for an all-black ensemble, make sure you wear it confidently with a matte red lip and bold accessories.

Dalas boots hotter

These Dallas ankle boots work brilliantly with leather pants or coated jeans.


Rocking fur lined boots

There is no better way to channel the chic Aspen winter vibes that with a pair of fur-lined boots.

Aspen chic

how to wear fur lined boots

With fur-lined boots, it is all about texture. Have fun layering multiple textural garments and accessories to achieve a casual, yet luxurious, look. These Truro fur-lined boots look stunning with textured/printed leggings or with these ultra slimline velvet jeans.  Feel free to experiment with other embellishments like pom-poms and faux-fur detailing.  Keep the color palette neutral and add pops of accent color and prints through your accessories.

textured chunky cardigans winter outfit

When styling fur-lined boots, it's all about texture.

Styling your go-to casual boots

An absolute must-have staple item for your wardrobe is a pair of trusty casual boots. These are the boots you can easily throw on for all of your everyday activities, knowing your feet are going to be snug and comfortable for the whole day. Sure, they may not be the most fashion-forward boots you own, but you can count on them to keep your feet from aching while you run around doing your daily chores and activities.  From walking the dog to last-minute grocery shopping, make sure you invest in a pair of boots with a lightweight supportive sole to keep you going throughout the day. Here is your inspiration for a casual, get things done, outfit:

Last-minute Christmas shopping

how to wear casual boots

For your relaxed, every day, look choose your favorite pair of worn-in jeans and layer them with a snuggly chunky knit. Choose a large scarf, in neutral tones, and add pewter accessories for a small touch of bling.  Throw on your Whisper Boots and know you can take on your day without having to worry about sore feet. Now go and annihilate that to-do-list!

Everyday casual outfit

We hope you have enjoyed your boot styling guide. Comment below to tell us your favorite look or what kind of boots you can't live without! If you love any of the boots featured in this post hop over to the Hotter Shoes website and enter the code UBKF40 for 40% off your order.


  • Reply
    Summer Reid
    November 29, 2019 at 9:09 am

    Love the studded ankle boots. Can you wear them with a dress?

    X Summer

    • Reply
      Mia Otilia
      November 29, 2019 at 9:13 am

      Hey Summer,

      Absolutely, I love wearing ankle boots with dresses. You can wear them with pretty much any length and go casual or quite dressy.

      X Mia

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