How to Wear Thigh High Boots for Any Occasion

January 2, 2019

Full disclosure: I’ve always been a massive fan of thigh high boots/knee high boots/over the knee boots, or whatever you’d like to call them.

I mean, isn’t everyone? Not only do they cover up your legs when it’s a bit nippy outside, but they also make you feel sassy AF when you’re wearing them.

And, in terms of what to wear with thigh high boots, you have a multitude of options regardless of their colour, fabric or detailing.

Whether you’re going shopping or heading out to meet a friend at a cocktail bar, this is my guide on how to wear thigh high boots if you want to make a serious style statement this season.

How to Wear Thigh High Boots for Any Occasion

(Please note that this post was produced in collaboration with Hidden Fashion and contains affiliate links, but all opinions are my own. For my full privacy policy, click here.)

1. With a Casual Jumper Dress

How to wear thigh high boots for casual occasions 101: team them with a snugly jumper dress. This is always a winning combination when it’s rather chilly outside and you need as much warmth as you can get.

For super wintry conditions, you could even throw on a teddy bear coat over the top as an extra layer.

(Beast from the East, be gone!)

Personally, I like to wear this wonderful combo for smart-casual events too, such as a meal out with the family.

In this instance, pick a printed jumper with more pizzazz as opposed to a plain version (leopard print is my pattern of choice right now) and then dress your outfit up with glamorous hair and makeup.

Either way, fashionistas take note: putting thigh high boots with a cosy knit dress ultimately helps them take centre stage and stand out for all the right reasons.

How to Wear Thigh High Boots   


2. With a Cute Skirt

Another option when it comes to how to wear thigh high boots? Combine them with a charming little skirt.

With checks being a huge hit for Autumn/Winter 2018/19, I’m currently obsessed with tartan skirts that would make the cast of Clueless undoubtedly jealous.

Or Regina George from Mean Girls. Why? Well, because vintage skirts = so adorable.

And guess what else looks unbelievably fetch? A check printed skirt with thigh high boots, a black roll-neck jumper and sparkly earrings.

In fact, just about any neutral-hued roll-neck jumper will work with grey or black thigh high boots, no matter what the colour palette of your check skirt is.

Don’t believe me? Try it out for yourself. I guarantee that you won’t be disappointed with this pretty yet powerful look.

Thigh High Boots Katie Davies UK Fashion Blogger


3. With a Glitzy Dress

Lastly, if you’re wondering what to wear with knee high boots going OUT out, wonder no longer!

For New Year’s Eve 2018/19, I decided to wear my black faux leather thigh high boots with the most dazzling sequin dress for utmost impact.

In fact, I’m a big fan of structured dresses like the one I’m wearing below, which hug your curves in a way that’s flattering yet supportive.

Texture clashing is also very on-trend for AW18/19 and looks killer for dressier occasions where it’s okay to embrace your inner maximalist. 

Not feeling a sequin dress to go with your thigh high boots club outfit? Opt for a blazer dress instead. When paired with minimalistic accessories, blazer dresses put a touch of chic elegance upon your entire ensemble.

AW18 Fashion How to Wear Thigh High Boots Without Looking Trashy


How to Wear Thigh High Boots

When done right, thigh high boots add a bold, stylish feel to your smart-casual, dressy or casual outfit.

If you’re wondering how to wear thigh high boots with jeans, stick to a skinny cut for practicality. And do not, under any circumstances, try to wear your thigh highs with any other type of trouser.

Trust me, it just doesn’t work!

Personally, I prefer the skirt or dress and thigh high boots combo every time, but only if the skirt or dress hemline sits a few inches higher than the boots themselves.

Either way, if you’ve never worn thigh high boots before, why not give them a go? You might just find that you love them as much as I do.

What do you think in terms of how to wear thigh high boots? Do you already own a pair? Let me know in the comments below.

Katie Davies is the Yorkshire-based freelance writer who founded The Trendy Tourist. In the last three years, she has written for over 100 companies on a range of subjects, from fashion to marketing. When she’s not producing content, you can find her shopping, exploring a new place or sitting somewhere having a cup of builder’s tea.

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