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.
The Street Pie
Style Notes: These are almost so sassy you can't resist them. Fendi's Rockoko Boots (£1090) have literally taken over the streets this past month.
The Style Stalker
Style Notes: Why not go the whole pirate panto and wear your tan boots with a swooping cape?
Style Notes: There's something about the cosy homeliness of a jumper dress that balances out the sass of OTKs.
The Street Pie
Style Notes: It's a classic combination that French girls are particularly into. Add in a checked blazer and you're looking at preppy 2.0.
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.
The Street Pie
Style Notes: If you've got a complicated outfit going on up top, just remember that black thigh-highs can help to ground a look.
The Style Stalker
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.
Getty Images
Style Notes: This season there are plenty of more colourful options on offer, should you want to make more of a statement. Colour-match and go.
The Street Pie
Style Notes: Suede, low-heeled over-the-knee boots are inherently retro, so wear them as such—with a mod-inspired miniskirt for example.
The Style Stalker
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: The addition of a furry coat and suede thigh-highs instantly ups the ante of a basic sweater-and–skinny jeans ensemble.
The Street Pie
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.
The Style Stalker
Style Notes: Over-the-knee sock boots have been blazing a trail all year long, with Balenciaga's fluoro versions recently taking the lead.
The Style Stalker
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.
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.
The Style Stalker
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?
Getty Images
Style Notes: Your over-the-knee boots can be used as a demure, body-lengthening tool when layered underneath a longer hemline.
The Street Pie
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.
The Style Stalker
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.
Getty Images
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.
The Street Pie
Style Notes: Denim shorts and over-the-knees make for a trusted L.A. go-to, but tailored shorts and flat boots feel far more appropriate for Europe.
Style Notes: By sticking to black suede extras, this girl-in-boots getup looks chic and easy.
The Street Pie
Style Notes: The overt allure of leather thigh-highs can easily be softened and cosier with just the addition of a lovely knit.
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.
Style Notes: Make a bold statement by clashing white boots with fishnet tights.
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.
Style Notes: A pair of black thigh-boots will serve you well and go with every other black thing you own.
Style Notes: If you can't put your skinny jeans down then vamp them up for the season with a pair of bold slouchy OTKs.
Next up, the autumn 2018 shopping list of your dreams.
