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Impossible Outfits: Curated by Tunde Ogunsina

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Between changing seasons, changing trends and changing plans, getting your outfit just right often comes down to a fine art.

As if these fashion dilemmas weren’t enough of a challenge already, we set Tunde Ogunsina the impossible task of curating outfits for the kind of scenarios that look great on your calendar but send your wardrobe straight into panic mode.

Given his history as a creative and as co-founder of the activewear brand Caro Padel, it came as no surprise that he rose to the challenge, leaving us with some fashion formulas and style picks we’ll be taking all the way into autumn and beyond.

Impossible Outfit 1: Hiking followed by afternoon tea

“I feel like this is one of those situations where people think you need two completely different outfits... but you really don't. I'd rather wear good quality pieces that can adapt throughout the day. Plus, I don't think my Grandma would appreciate me turning up looking like I'd just climbed a mountain.”

Key Pieces

Impossible Outfit 2: Hyrox by day, brand event by night

“This feels SO ME. This is less like a hypothetical and more like my calendar. I don't want to be carrying a suitcase around London, so I'm always looking for pieces that can completely change the vibe with a couple of swaps. Throw on tailoring, add some jewellery and suddenly you're ready for an event without starting from scratch.”

Key Pieces

  • For the active half of the day: a Gymshark matching black set and trainers you trust

  • Swap out your gym bag for a Piquadro leather tote

  • When it’s time to switch, in comes an oversized white Oxford shirt from COS

  • Finish the look with AllSaints wide-leg tailored trousers and black loafers

  • Add jewellery from APM Monaco as the finishing touch

Impossible Outfit 3: “Casual”

“I don't trust anyone who says 'just come casual'! Nine times out of ten, everyone interprets it differently, so I'd always rather sit somewhere in the middle. A relaxed suit with softer pieces underneath means you're covered whatever everyone else decides to wear.”

Key Pieces

  • A relaxed black suit trousers from Theory for dressing up/dressing down

  • Add a black knitted polo from Boggi Milano

  • Keep things relaxed with loafers from Michael Kors

  • TwoJeys brings the fun silver accessories the outfit’s asking for

  • If it turns cold, a wool overcoat from Yosqi has you covered - literally

Impossible Outfit 4: Filming all day in unpredictable weather

“Honestly, this is just every filming day in London. You leave the house in sunshine, get caught in rain an hour later and somehow it's sunny again by lunch. I've learned the hard way that layers are non negotiable. I'd rather have a jacket I don't need than need one I didn't bring.”

Key Pieces

  • A pair of comfy trainers from On

  • Some relaxed trousers and a crisp tee from UNIQLO

  • A Levi’s overshirt adds colour

  • A cap from Armani Exchange adds cool-without-trying cool

  • A lightweight waterproof shell from 66°North goes in the bag regardless of what the forecast promises

Impossible Outfit 5: Fashion Week but you only have a carry-on

“I actually love the challenge of this. If an item only works with one outfit, it's probably not making it into my suitcase. I'd much rather pack a few really versatile pieces that I can mix and match. It saves space, but it also stops those "I've got nothing to wear" moments when you're away.”

Key Pieces

And there you have it! Proof that great style that passes the versatility test only takes a little bit of thought and creativity. Whatever the day throws at you, Regent Street's got the wardrobe for it. See where to build out your autumn wardrobe, which trends are sticking around for the season ahead, and where to shop at London’s most famous locations. Make sure you tag us in your looks - @RegentStreetW1 on Instagram and TikTok.