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Your winter boot prescription starts here.


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  1. Nothing fits.
  2. Maybe I’ll just donate all my clothes.
  3. I have nothing to wear.

One or all of the above sound like you? It’s entirely possible you’re experiencing the September sartorial itch. Closet questioning is a common symptom of the tide coming in on a new season. Though, instead of spending a healthy portion of your pay cheque on building a wardrobe from scratch, it’s much more effective to invest in one or two timeless pieces per season that will go the distance, elevate multiple outfits and, most importantly, your mood.

Winter boots are a perennial classic. A big trend this season: Cowboy boots. Isabel Marant, Ganni and Off-White (to name a few) have nailed this footwear category. Though perhaps they need to come with a warning symbol - of what to actually wear with them. The street style trick = CC (clever contrasts). Avoid anything too Western-y elsewhere, so as not to veer too much into costume territory. Instead, pair with classic pieces (think oversized blazers, jeans and a T-shirt) or tuck into a pair of camel or grey suit trousers.


For something less directional, you can’t go wrong with a classic black Chelsea boot (polished and ultra-functional). Want a ‘semi-statement’ boot? A style that has a point of difference, but isn’t too OTT that limits its everyday wearability? Seek out a square toe or sculptural heel (see Manu Atelier, Nodaleto and YUUL YIE).

If a re-boot is in the works, see our curated edit of the best new autumn / winter boots worth breaking-in, for all your needs. Walking, hiking, (at-home) partying -there’s a style to suit everyone.

To quote Rachel Green, “They're my new "I don't need a job, I don't need my parents, I've got great boots" boots!”

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