HERE’S WHAT TO WEAR FOR A FIRST DATE – AND THE NEXT ONE

What is the best outfit for a first date? Well, this is probably the most daunting of all romantic meetings, with plenty of dos and don’ts to navigate. But your outfit should be incredibly easy. Think in simple terms: you want to present the best version of yourself, whilst staying authentic to your usual style. There’s no use throwing together an ostentatious first-date outfit if you don’t plan on wearing it again. Plus, your date might have some questions if your wardrobe suddenly pivots by date number 2.

If you’re particularly stumped, we’d recommend a simple T-shirt and smart-casual trousers (structured cargos or jeans are a great choice). And when it comes to what shoes to wear on a first date, simply finish things with your go-to shoes – be it trainers or loafers – and a really good jacket to tidy things up. This season, suede and leather are trending, so consider weaving these fabrics into your outerwear or accessories.

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The definition of a ‘drinks date’ is relatively vague, so the accompanying outfit can throw up a few questions: are jeans okay? What’s the best colour to wear? Start with the setting – is it a pub? Cocktail bar? Dimly lit small plates establishment? These factors will sway your ensemble. For the former, opt for something comfortable like a cosy knit and textured trousers (cords are great for autumn), while a cocktail bar might require something a touch more formal. If you’re not a shirt-and-tie kind of guy, focus on tailored trousers and smart shoes paired with a simple top. As they say, it’s all about balance.

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Topman diamond knitted jumper in ecru, £42
ASOS DESIGN baggy trousers in black corduroy, £32
Bershka wide leg tailored trouser in brown, £29.99
Bershka three tone mock toe deck shoes in black, £55.99

A casual date outfit shouldn’t necessarily look like your usual loungewear get-up. (Unless this is a no-frills hangout with your long-term beau). Perhaps you’re partaking in some kind of activity like bowling or just chilling out to watch a movie. This is a great chance to lean on more elevated basics, like structured sweatpants and a crisp tee. Quality is your secret weapon here, and a heavyweight polo or jumper will make even the most low-profile looks feel thought-through. If you’re particularly eager to impress, reach for timeless, luxe staples and leave no stone unturned. In other words, don’t sleep on a good pair of socks!

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ASOS DESIGN co-ord relaxed polo sweatshirt in grey marl, £26
Champion barrel joggers in black, £43
adidas Originals 2 pack ribbed crew socks in brown, £15
Asics Gel-Kinetic Fluent trainers in white and marzipan, £180

If you live in a busy city, your quest for love is going to involve a few coffee dates. They’re convenient, friendly on the wallet and a great option if you have evening plans. You can even slot these meet-cutes in between work meetings, so your wardrobe should be versatile and practical.

The key is to look like you threw everything on without thinking about it. Start with a tonal preference – like trending burgundy or navy – and build out from there. A colour-drench outfit is always easy and packs a punch, while classic jackets like the Harrington or bomber jacket are trusty staples you can always rely on for a boost.

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ASOS DESIGN leather look jacket in navy, £55
Threadbare straight fit trouser in navy, £24
ASOS DESIGN super oversized boxy fit knitted fisherman rib jumper, £36
ASOS DESIGN sling cross body bag in black, £22