23 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.

1. Go for gloss red and pointed toes.
Over the knee boots outfits

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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.

2. Wear with a cape for dramatic effect.
Over the knee boots outfits

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The Style Stalker

Style Notes: Why not go the whole pirate panto and wear your tan boots with a swooping cape?

3. Sweaterdresses and thigh-highs are a perfect match.
Over the knee boots outfits

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Style Du Monde

Style Notes: There's something about the cosy homeliness of a jumper dress that balances out the sass of OTKs.

4. Borrow from the boys.
Over the knee boots outfits

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Vanessa Jackman

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. Slouchy finishes are back.
Over the knee boots outfits

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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.

7. Don't assume your boots have to be neutral.
Over the knee boots outfits

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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.

8. If you're brave, try an oversize hoodie.
Over the knee boots outfits

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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.

9. Use them to elevate skinny jeans.
Over the knee boots outfits

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Style du Monde

Style Notes: The addition of a furry coat and suede thigh-highs instantly ups the ante of a basic sweater-and–skinny jeans ensemble.

10. Colourful sock boots are key for A/W 17.
Over the knee boots outfits

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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.

11. Monochrome is always a wise approach.
Over the knee boots outfits

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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.

12. Just reveal an inch or two of leg for a risqué moment.
Over the knee boots outfits

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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.

13. There are so many iterations, you can choose a version to suit.
Over the knee boots outfits

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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?

14. Layer long-over-long on more ladylike days.
Over the knee boots outfits

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Style Notes: Your over-the-knee boots can be used as a demure, body-lengthening tool when layered underneath a longer hemline.

15. Wear oversize short shapes to counteract slimline legs.
Over the knee boots outfits

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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.

16. Multiple hemlines also work with over-the-knee boots.
Over the knee boots outfits

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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.

17. Do try pairing them with everything you own.
Over the knee boots outfits

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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.

18. Match up your accessories.
Over the knee boots outfits

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Vanessa Jackman

Style Notes: By sticking to black suede extras, this girl-in-boots getup looks chic and easy.

19. Tan suede looks good with summer's cotton dresses.
Over the knee boots outfits: suede thigh-high boots worn with a smock dress

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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.

20. Try white boots for a lighter look.
over the knee boots outfits: white thigh-high boots worn a blue dress

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Style Notes: Who says your boots have to be super-wintry? Try some white or light boots with bare legs and a trans-seasonal dress for an outfit you can wear many days of the year.

21. Your sweater dress and boots can match.
Over the knee boots outfits: cream lace-up thigh-high boots worn with a sweater dress

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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.

22. All-black textures are always good.
Over the knee boots outfits: black pull-on embellished thigh boots worn with a vinyl trench coat

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Style Notes: A pair of black thigh-boots—even patent ones—will serve you well and go with every other black thing you own, as well as the rest of your wardrobe.

23. Don't forget your party boots
Over the knee boots outfits: pink thigh high boots worn over skinny jeans

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Style Notes: There's plenty of mileage you can get out of your favourite OTKs with a party dress.

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

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