28 Street Style Looks That Will Persuade You Into Wearing Thigh-Highs This Year

Thigh-high boots have an unfairly bad rap. Rather than thinking of, say, the nattiness of Puss in Boots, it's easy for our minds (and, on occasion, anyone's outfit) to easily veer into Pretty Woman territory. We believe these supposed hurdles shouldn't be met with instant defeat, and the fact that designers and high-street stores have continued to produce them year after year says something. From personal experience, we know each autumn season the concept of wearing over-the-knee boots gets that little bit easier.

The proof is in the retail pudding: If the style keeps coming back every time the temperatures dip, there must be plenty of girls out there acing the thigh-high game already. We do understand if you still have reservations, but in general, this has become a trusted boot trend that started off in plain, safe black iterations (still entirely legit to wear these now, if you're starting out) and has since moved into more adventurous realms—don't be surprised to see bright red suede or patent leathers cropping up for A/W 18 (just one look at Balenciaga's offering and you know things are about to get serious).

To help you out, we've put together a handy guide to wearing these no-longer-raunchy boots in as many fashion-focused ways as possible. Scroll through for 28 foolproof style tips when stepping into thigh-high boots.

Next up, the autumn 2018 shopping list of your dreams.