Fashion Women's Fashion

I Tried On 50 High-Street Dresses to Work Out Which Ones Go With Boots

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Here at Who What Wear UK, we’re all about delivering the latest and greatest shopping edits, as approved by our team. That’s why we’ve created a new shopping column, The Joy of Shopping, which will see me, Joy Montgomery, heading to all your favourite stores to test out new-in pieces IRL. From summer dresses to the brands you might’ve forgotten about, prepare for changing room selfies aplenty. Is there something you’d like me to cover? Make sure to tweet or Instagram me your requests!

One of my favourite moments in The Devil Wears Prada is when Andy Sachs sashays into the office clad in a pair of leather thigh-high boots. “Are those the…?” Asks Emily open-mouthed. “The Chanel boots? Yeah they are”, replies Andy with a serene smile. Much like Julia Roberts’ Pretty Woman power suit or Sandy from Grease’s biker-jacket-and-perm makeover, these boots become a marker of Andy’s new ‘don’t-mess-with-me’ persona—a gateway into a strange new world. Yup, fashion can change lives, kids. 

I might not be rocking Andy’s designer stilettos, but I can certainly testify to the outfit-transforming powers of a good boot. Three years ago I purchased a pair of black knee-highs from Zara, and last year was kindly gifted some chunky lace-ups from ASH. They have both been loyal companions over many a cold winter morning and, sartorially speaking, there’s not much they can’t do. 

From my experience, you can cover most bases with this boot power duo. My knee-highs are perfect for adding a grown-up polish to any outfit, while lace-up boots have a more toughened, cool-girl edge. This season in particular there seem to be a surfeit of winter-ready frocks that are begging for a good boot pairing: From floaty midis and jumper dresses, to thigh-grazing smocks and tweed minis. I’m also using my boots (and good ‘ol roll neck) to adapt my favourite summer dresses for the colder months. 

Not sure where to start? Let me be your guide. Jumper dresses have made a serious comeback this season and exude minimalist chic when worn oversized with knee highs—Arket is great for quality pieces. There’s also a resurgence of minis, which will look just as good with heels, for a little ’60s styling, as they will with flats (very Alexa Chung). There’s also plenty of classic long-sleeved midis and work-ready shirt dresses to go around. Scroll down to see and shop my full edit.

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