The other day I was attempting a clothing cull when I got a bit distracted and started trying on the clothes I was considering taking to the charity shop in combinations I hadn’t put together before. I threw an army jacket over a maxi dress. Tried on a pair of trainers with a leather midi skirt. Paired a stripy tee with a floral skirt. Slung my biker over a smart office-appropriate dress. Tried my fanciest top on with my most destroyed pair of jeans.

And you know what? Nearly everything I tried worked. Clothes that I haven’t worn for years suddenly felt fresh. Things that I barely wore in the first place have gone into regular rotation. The leather midi skirt that I bought on sale in The Gap in Charleston – of all places – in the late 1990s, that has rarely seen the light of day because I could never work out what shoes to wear with it, but I couldn’t bring myself to get rid of it because it was such a bargain, has made several appearances worn with my new flyknit Nikes since my clothing-cull-that-wasn’t.

You’ve probably got some of this stuff in your wardrobe already, but if you haven’t I’ve found some looky likies on the high street (not at 1990s prices, sadly).

Biker Jacket + Smart Midi Dress

I’ve said it before but it still stands, I never like to look too smart and throwing a biker over a tailored dress takes it down a couple of notches smartness-wise to a level I can handle.
Leather Biker, £119.99, Mango. You can buy it here. Crinkle Cut Out Back Dress, £75, Finery London. You can buy it here.

Long White Dress + Army Jacket

Throwing an army-style jacket over a strappy floor-sweeping dress makes it feel a bit less fancy and/or shoulder-exposing and will keep you warm on the way home from a summer evening out even after the temperature’s dropped.
Off-white long flowing dress, £29.99, Zara. You can buy it here. Multi-pocket jacket, £45, Topshop. You can buy it here.

Graphic Stripe Tee + Flippy Floral Skirt

A fitted graphic stripe tee worn with a flippy bold floral skirt is a surprisingly chic combination for summer parties.
Short sleeve breton, £22, Boden. You can buy it here. Floral print midi skirt, £48, Topshop. You can buy it here.

Fancy Top + Destroyed Jeans

Like a magpie I’m drawn to anything sparkly and the more worn my denim the better, so I can’t think why I never tried this combination before. Better late than never I guess.
Ombre sequin top, £110, French Connection. You can buy it here. Cropped slim-fit jeans, £39.99, Mango. You can buy there here.

Leather Midi + Trainers

I was very happy to discover how well this pairing worked. Top-wise I’m wearing it with a fitted denim jacket worn as a top, also from the 1990s, but it would look good with a sporty sweatshirt or an oversized unisex-style shirt.
Leather peplum skirt, £119, Finery London. You can buy it here. Nike Roshe Run Jacquard Trainers, £75, ASOS. You can buy them here.

Anyone else started wearing something old in a whole new way? Got an item of clothing in your closet that you can’t bring yourself to get rid of but you’ve barely ever worn? Anyone bought anything from Finery London yet? I think I’ve found my new workwear go-to site. And the next time you have a spare half an hour, pull together the clothes you’ve mentally earmarked for eBay or the charity shop. Try them all on again before you part ways, with something you’ve never worn them with before, you just never know…

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