What To Wear To A First Date For Men: Pros And Cons

Not the flip flops.

05/08/2016 15:17

Figuring out what to wear on a first date may be a last-minute consideration, but trust us when we say it makes a permanent (often irreversible) impression.

Don’t ask your mum or your best mate for last minute advice, we have it sussed if you’re dithering about what to wear.

Flip Flops

Pros: You don’t have sweaty feet, will never look overdressed, and feel relaxed (like you’re on the beach). 

Cons: Unless you’ve been for a pedicure in the last six months, we’re pretty sure your toenails will make this a non-starter for you. 

Flowery Shirts

Pros: They show a lot of personality and are generally quite flattering. 

Cons: They make every man look like Philip Green. EVERY man. 

Andrea Cappelli via Getty Images

Slogan T-Shirt

Pros: If the slogan is funny or a band/celebrity that your date likes too, then it’s an instant ice breaker and conversation starter.

Cons: If it is politically incorrect in any way (for example, FBI: Front Bottom Inspector), you can forget it. 

Low Cut Vest

Pros: No ambiguity about how good you look naked. You’ve spent a lot of time in the gym and you’re going to show off your hard work, dammit.

Cons: There are very few appropriate public places for your nipples to be on show. 

Rosary Beads

Pros: You seem like you’re from a good family, you probably spend a lot of time with your grandmother and have strong feelings on marriage and procreation.

Cons: It’s not 2005. And you’re not Pete Doherty.


Apple Watch

Pros: They look so damn cool.

Cons: You end up checking your emails/being an anti-social twat all night.


Pros: Is there anything sexier than a man who clearly looks after himself and didn’t just have a wash with a damp flannel?

Cons: Go overboard and your date’s going home with a migraine.


Pros: Prematurely balding patch? What prematurely balding patch, we say, now that you have the topiary version of Spanx concealing everything on your head.

Cons: No one, apart from possibly Paul Weller and David Bowie (RIP) can pull off a hat inside a pub on a Thursday night.

Football Shirt

Pros: You make your allegiances known early on, and if they support the same team as you, instant winner.

Cons: You’ll look like their brother. Or worse, dad. 

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Pros: Scientific studies have shown that you are definitely going to look better with sunglasses on, as they correct the misshapen symmetry of your face.

Cons: You will have to take them off at some point, even if that is as you get into bed...

Linen Trousers

Pros: You feel light and breezy, and it reduces the risk of sweaty balls.

Cons: You look like a yoga teacher from Brighton or at best, a young version of Ernest Hemingway. 

Shaved Lines In Your Hair

Pros: You look like you could protect her in a fight.

Cons: You will be the one starting the fight. 

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