The definitive guide to dressing for a date


Dressing for a date can be a troublesome affair. In all of life’s occasions that involve first impressions, dates are up there with the ones that count most. So to make sure you walk into your next date worry-free, follow our guide to date night dressing – whether it’s the first encounter or the umpteenth.


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First date

Perhaps the most nerve-wracking of them all, the first date is filled with a lot of unknowns. One thing’s for sure though, when it comes to outfitting for multiple possible scenarios, playing it classic and understated is a good bet. The key is to look pulled together but still relaxed, effortless rather than trying.


If your meeting involves some kind of outdoor escapades, we recommend a clean-line parka. For a day date or coffee, a flannel shirt layered over a roll neck top works well. For evening drinks, a great light knit or an Oxford shirt. Bottoms-wise, it’s hard to go far wrong with denim. For more casual settings, choose light or distressed denim and minimalist sneakers. For after-dark rendezvous, go for dark denim and boots. Actually, that wasn’t that daunting was it?



Fifth date

Having got this far, you can now have more fun with your dating wardrobe. Show some personality but remember to keep it approachable and appropriate to whatever activity you’re undertaking.


A nice bomber jacket, printed shirt and tapered trousers would suit cool, swankier places. A trendy quarter zip-up, jeans, trainers and chunky socks would work for a meeting that might involve a whole day of gallivanting. The polo neck has got that retro, cool vibe. Team with a great overcoat and tailored, herringbone trousers.


Date six? We think it’s a given.




Now here’s the one where you want to actually demonstrate you’re making an effort. Start with grooming. Hair, nails, a great scent, and build your outfit from that.


For such an occasion as this, we recommend looking a little fancier than normal. Go for a grey suit jacket, simple tee underneath and suit trousers cut just above the ankle with box-fresh trainers, or a close-fitting, heritage three-piece suit with brown brogues.


Save your whimsical tie for the office do and leave your work outfits at home. This is the time to look serious but not like you’ve just run straight from a pile of paperwork. Opt for suave and classy and just by your outfit, you’ll show your partner what the occasion means to you.



Date night

Designated date night? When you’ve been with your partner for however many years, we suspect they’ll know your wardrobe inside out. So the key to date night dressing is to whip out something new. Think luxury and great quality fabrics. A beautiful charcoal blazer, a great watch, fancy but not kitsch loafers. Bring out a new investment – paired with a refined, coordinated ensemble – and you’re on to a winner. Surprising your partner is always a fun start to designated together-time. Wardrobe-wise, we think we’ve cracked it.