film 1992 julia roberts pretty woman gif pretty woman GIF

It all started when Kendall Jenner posted a typically unsubtle instagram snap wearing a pair of Vetements X Manolo Blahnik waist-high boots, a cowboy hat, and not much else. I figured, if she can do that, it’s probably about time that I got over my issue with over-the-knee boots. Thanks for the intervention, K. It’s a style I’ve never been quite confident enough to embrace – all thanks to Pretty Woman’s Vivian Ward.

When Julia Roberts’ Vivian marched into that Beverly Hills boutique to tell those snobby sales gals about their ‘BIG MISTAKE’ she immediately became a style icon. That cut-out body-con dress, blonde wig and knee-high patent boots combo is arguably one of the best movie looks ever. It’s right up there with Cher’s plaid skirts in Clueless or anything from Margot’s wardrobe in the Royal Tenenbaums. I think it’s safe to say though that most people would aim to channel the post Richard Gere Viv vibe instead.

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So classy. Don’t get me wrong – I’m so there for Vivian’s bad-ass sass but I’m pretty sure that outfit has given people OTK anxiety – *searches ‘can I wear over the knee boots without looking trashy’*. Combine that with the fear that the Kinder Bueno we stuffed in our face at lunch will mean our boots barely even make it over our ankles and it really is a pretty daunting trend.

Well ladies, Walt Disney said that ‘all our dreams can come true if we have the courage to pursue them’, so it’s time to get some courage and face the fear of having to be cut out of a pair of boots in the middle of a shop. Maybe I’ll even look as good as KJ or Ms. Ward. A girl can dream. So we’ve taken it upon ourselves to put together some OTK looks that you can be confident won’t leave you looking like a lady of the night.

Look 1: Paying Homage

Double image of model wearing schuh flex boots in khaki

schuh Flex 

Over the knee boots and a faux-fur jacket… you might be nervous that this is a little bit ‘Pretty Woman’ – but it’s merely paying homage. And the key to keeping it classy comes in the form of keeping things covered up – black jeans and a chic high neck-line will do the trick. Think of this as your perfect sassy enough for a hip pop winter look. Plus they’re super stretchy – so you don’t have to worry about getting stuck in them!

Look 2: Business at the Top, Party at the Bottom

Double image of model wearing schuh runner boots

schuh Runner

This classic preppy vibe is made so much cooler with some flat black OTKs. It’s like the teacher’s pet went a little bit wild… just a little bit. If you’re really worried about looking ‘trashy’ then flat boots are the one for you.

Look 3: Feelin’ Like a Grown-Up

Double image of model wearing schuh epic boots in red

schuh Epic

This look just screams ‘I am a sophisticated, classy woman’ – it’s boho but in a put-together, fashion editor sort of way. A looser fit gives these a more relaxed look – great for nailing that always difficult smart-casual vibe. This is the perfect transitional outfit – swap your heeled sandals out for these bold red beauties and you’re ready for autumn.

So go on. Brave it. We can’t promise you’ll look like Kendall Jenner, or Julia Roberts – but you will definitely look fantastic.