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.
Style Notes: On the other hand, you can try a more masculine-inspired look with your thigh-highs, as Man Repeller's Leandra Medine does in an oversize blazer. Again, the contrast helps diffuse the va-va-voom of the boots.
6. Smart short skirts look best with plain black boots.
Style Notes: Slouchy '80s-style boots are back in over-the-knee form. They're best worn with an expanse of bare leg in order to flatter out the excess of leather and make it clear that your pins do exist.
Style Notes: This bold look won't be for everyone, but if you're the kind of girl who think Yeezy's creations are tame, try an oversize hoodie with OTKs.
Style Notes: Considering there are plenty of handkerchief and asymmetric hemlines going on right now, you may as well make the most of a trend and wear your thigh-highs with them.
Style Notes: It can actually be easier to wear one bright colour head-to-toe than trying to season an existing, more sombre look with something punchy. This is a prime example of the idea in action.
15. Just reveal an inch or two of leg for a risqué moment.
Style Notes: Take your cue from Olivia Palermo and wear your over-the-knee boots with a miniskirt for a date night–worthy ensemble. The pairing will reveal just a sliver of skin for a look that's sultry yet understated.
16. There are so many iterations, you can choose a version to suit.
Style Notes: This season, you get to choose which OTK style feels most "you"—are you a leopard-print, no-heel kind of girl, or a Swarovski-encrusted £5570 woman?
Style Notes: What's great about just having some body-hugging boots on your bottom half is that you can experiment with voluminous minidresses, coats and sweaters, and you won't look or feel bulky.
19. Multiple hemlines also work with over-the-knee boots.
Style Notes: It can be easy to think you need to keep things simple with a dress that hits the top of your boots, but experimenting with layers of varying lengths can be really effective too.
Style Notes: You just never know when an unexpected combination could strike the right note. We never thought overalls and over-the-knees could work, but here is the outfit that bucks tradition.
Style Notes: Camel, beige and brown tones work together 365 days of the year, so you can mix your seasonal pieces together easily with a pair of chesnut-suede over-the-knee boots.
25. Try white boots with black tights for a change.
Style Notes: As far as leg-elongating hacks go wearing a same-tone sweater dress and OTKs is up there with the best. This Peter Pilotto knit ticks the box nicely.