How to master the art of transeasonal dressing

Bec Oakes 18 October 2021

As the nights creep in and the winds get colder, here are some easy ways to switch your wardrobe with the seasons 

Dressing for the unpredictable British weather can feel like a minefield and never more so than during the tricky transitional period between seasons—that time of year when one minute there are blue skies, the next torrential rain.

There’s nothing worse than going out sans jacket only to get caught in an unexpected rainstorm. And, on far too many occasions, I’ve dressed for a blustery morning in my finest wool coat, then overheated as the temperature rose at lunchtime. 

When weather conditions at opposite ends of the spectrum collide in the space of 24 hours, it makes it pretty damn difficult to know what to wear. Enter transeasonal dressing—style built around seasonless wardrobe essentials. And it’s not as complicated as you might think.

Whatever your personal style, all it takes is investing in a few versatile pieces so you can tackle whatever these awkward in-between days throw at us without breaking a sweat… or getting a chill.

Get in the right mind-set for transeasonal dressing by steering away from an excessive amount of summer or winter items. Beach cover-ups and straw hats or heavy overcoats and thick knits are great in extreme weather conditions but will quickly find their way to the back of your wardrobe as soon as the temperature changes.

Instead, fill your wardrobe with pieces that can be mixed, matched, adjusted and layered as needed. Think cotton t-shirts, straight-leg jeans, lightweight jackets, leather ankle boots and loafers.

Equally, you can truly make the most out of your wardrobe by going back to basics. Opt for high-quality timeless staples in easily translatable colours (ie, neutrals) that will provide the foundations for endless stylish ensembles season in and season out. Then, as seasonal trends come and go, simply add a few that you love to your outfits and you’ll be looking good on all fronts.

"You can truly make the most out of your wardrobe by going back to basics"

And how do you ensure you’ll be warm but not too warm? Cool but not too cool? Comfortable yet stylish? The key lies in layering. Whether it’s a breathable knit, a lightweight jacket or a silk scarf, at the centre of any transeasonal wardrobe is an army of versatile layers that can be thrown on or shed as the temperature shifts throughout the day. 

Layering also allows you to wear your favourite summer pieces for longer. This summer, oversized cotton shirts were a must-have piece, worn with denim shorts, over bikinis and belted à la Carrie Bradshaw. Give your shirt a new lease of life by pairing it with a sweater vest, your most flattering jeans and crisp white trainers to beat the October chill.

I’ll be elongating the life of my favourite piece from summer 2021—the Batsheva "Amy" dress— by layering it over a turtleneck with lug sole boots and adding a puffer coat as the temperature continues to drop. 

As the seasons shift, have fun mixing, matching, adjusting and layering pieces to curate a wardrobe that is both comfortable and stylish, making the transition between summer and winter seamless. 

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