The Sky is the Limit: How to Wear Thigh High Boots


Can we talk about the thigh high boot for a minute? We went to the knee, then over the knee, but this boot takes it to a whole other level. I know that many of you suffer from visions of the dominatrix or of Julia Roberts character is Pretty Woman with her lady of the night length, but lets re-think things for a minute. These don’t have to hold such associations. These are warrior boots.  They are rockstar boots. They are superhero boots. Catwoman would never be caught dead in the shootie. And Wonder Woman’s costume would have been so much better if those boots kept going for another foot. So let’s reassess the thigh high boot and explore how to wear one of this season’s hottest boot trends in a way that looks awesome, sophisticated, fashion forward and age appropriate, and let’s put those former impressions behind us.

Olivia Palermo - thigh high boots

The first thing to consider when wearing the thigh high boot is what will you pair it with? This boot is meant to be seen in all its glory so why bother hiding half of it under a pencil or midi length skirt. Don’t worry though, you still can wear it with these slightly longer skirt lengths, especially when it comes to the office. Plus I’m a fan of getting mileage out of all your wardrobe pieces, and boots don’t come cheap, but this boot is meant to be the star. That being said, it works best with a very short dress or skirt. Think almost a micro mini length. You want to have a tiny bit of skin (maybe 2″-4″) showing between the skirt hem and where the boots begins (or is that ends?). Another option is a skirt or dress with a high slit up the side so that one boot peaks through as you walk. Wear it either with a bare leg or a sheer hose. A touch of skin is the raison d’être for the thigh high boot. I know it seems scary, but trust me that when executed right, it’s gorgeous.

How to pair thigh high boots?

With a Skirt

Pair it with a very short skirt. Try a narrow mini, the skater skirt, or fit and flare. Aim to have a small amount of skin or hosiery showing between the skirt and the boot.

thigh high boots - mini skirt

With a Dress

Try it with a slightly looser fitting short sweater dress that bands around the bottom. A shirt dress is equally gorgeous with it. Same goes for a tunic style.

thigh high boots sweater dress thigh high boots tunic

With Shorts

Try it with a beautiful pair of fall weight short shorts. Leave a hint of skin between the boot and short hem.

thigh high boots - shorts

With Pants

For those that are never going to wear the  micro mini length, leggings are a great option. Leather ones would be particularly fabulous. Jeggings or a very skinny jean are equally great.

thigh high boots - jeans

Why it works?

The minimal amount of skin showing is the reason why it works. The boot actually covers up most of your leg. Can you imagine the micro mini with a boot that goes to the knee. That’s where it takes a riské turn, but the to-the-thigh fills in all that space and you get just the slightest peak-a-boo effect. My preference is suede over leather because I find that it softens the look, but I wouldn’t pass up leather ones if a pair landed in my lap. I just find that it is tougher looking over the richness of suede. I really like the softer colours like dove grey, cream, brown or camel tones, and unexpected colours like navy blue, but black is always a great basic and so easy to pair with most everything.

My tip is to stay conservative on the top half. A crisp, white shirt is always fail proof. Try a boxy sweater, blouse or boyfriend blazer to offers a great juxtaposition to this look, or a hip length chunky sweater for a super top-to-toe pairing option. Boho pieces like a fringe bag also tone down the look, yet keeps it very fashion forward. Or consider a classic quilted Chanel bag for elegance.

Flat, a small heel or a 5″ stiletto are all available to try. For those that are a tad shy, go for a flat or a chunky 2″ heel. For those that are the go-for-it gals, I say the stiletto all the way.

Who can wear thigh high boots?

Unfortunately, this boot is limited by the size of your thigh. Too much thigh and it won’t fit. Too thin of a thigh and it may slouch a bit or you may find it sliding down. But if you love your legs, give it a try.

Aldo currently has a gorgeous grey suede pair (the Seania boot) that is on my bottomless bucket list – can you have a shopping bucket list? They have similar ones in an almond toe and in a pointed toe stiletto. Stuart Weitzman has gorgeous thigh high boots, if you have deeper pockets (check out the Highstreet boot). Looking for a New Year’s Eve look? Banana Republic has a gorgeous cream and grey sparkly mini skirt to wear with these boots.

Aldo Seania Boot


Banana Republic Mini

Banana Republic

I am in love with the thigh high boot. Let’s reach for the stars, or at least to our thighs and go for it.





Carolyn Bissett


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