6 Things No Man Should Wear On A First Date


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First dates are always going to be a stressful experience; you’re jacked up on the could-be-lethal combination of adrenaline, the pressure to be charming and the hope of getting laid, with the added danger of getting wired on coffee or drunk on alcohol.

So the last thing you need is extra worry about the sort of style slip-up that’ll have your date openly feigning the squitz just to escape. First impressions matter, even post-Tinder, which is why we’ve pulled together the definitive list of what not to wear. Swipe left on all of them.

(Related: 5 Date Night Looks For Men)

A ‘Hilarious’ T-shirt

If you’re the kind of guy that buys his basics at a tourist trap in central London, you need to stop right now.

Any slogan or image emblazoned across your chest that has to be justified with the words, “Chill out, it’s just banter, innit,” is going to be a turn-off.

This rule is amplified when the T-shirt in question is even vaguely misogynist or creepy, so save your ‘FBI: Female Body Inspector’ and ‘Sex Instructor: First Lesson Free’ designs for painting the house or, you know, when you’re short of kindle for a bonfire.

In fact, we’re going to say that any kind of slogan T-shirt should be off-limits, even that one that says “Pick flowers, not fights”. In short: it’s you who should be hilarious, not your shirt.

What To Wear Instead

“A guy’s main aim on a first date is to not scare (or offend) his date away from the get go. Instead of a slogan T-shirt or anything with a bright eye-watering print, opt for a shirt in a subtle colour such as white or sky blue – it’s the perfect in-between to avoid dressing too smart or too casual.” Gordon Richardson, Topman creative director

shirts to wear on a first date

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A Bare Ankle

Controversial, perhaps, but mankles are Marmite in the dating world, so it’s best to err on the side of caution and go all Victorian by covering them up for an initial meet.

An ankle sans-sock is likely to conjure up one of two distinct images of what lies beneath: that of the deeply divisive trainer sock – a piece of clothing that, yes, might be essential, but which can never be described as sexy.

Alternatively, your date might assume that you’re, shock horror, actually sockless. Given that it’s date number one and they have no idea how thorough your hygiene regime is, it could be taken as an indicator of pongy toes. It’s never good for your date to get even a whiff of the idea that your feet might smell.

Save that flash of lateral malleolus for those future dates that, now you’ve listened to us, are a lot more likely to happen.

What To Wear Instead

“This depends on your shoe of choice; if you’re a dapper chap in a pair of brogues, go with a bright flash of sock. If in a pair of trainers, tube socks are your friend. Another tip for gents of a shorter stature, wear socks that are the same colour as your trousers. This will give the illusion of a longer leg and will improve your overall silhouette.”

Giles Farnham, head of the River Island Style Studio

how to match shoes and socks

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Your Work Suit

While a date can easily fill you with the same crippling levels of anxiety as a job interview, just remember it isn’t one. The whole experience should be fun and, if possible, you should feel (or at least appear to be) relaxed rather than sitting fiddling with the tie you’ve been knotted into since 9am.

Of course, if it’s a weekday date, going home from work to change beforehand is not always an option. To avoid making your date feel underdressed, or making yourself appear a bit of a stiff, show some savvy and make a few sartorial switches deskside.

What To Wear Instead

“You can completely change the perception of your outfit with a few small changes. A smart T-shirt or a lightweight crew neck knit, to replace a shirt and tie, and a sharp pair of trainers can be game changers.”

Designer Charlie Casely-Hayford

how to make a suit less formal

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Political Merchandise

Unless you’re an actual card-carrying member of a political party and steadfast in your conviction of never dating anyone with opposing views, it’s best to bin the badge and leave the tote bag at the door.

As every good dinner party host knows, politics and religion are two subjects that should never be discussed at the table. The same applies for dates. There are few things as off-putting as someone inflicting their political opinions on you. Besides, you don’t want to immediately discount your date just because they happen to like Theresa May’s shoes.

Things that might be important when moving in together or popping out kids – like your stance on private education – are not first date fodder, so don’t even tempt yourself with a sartorial segue into conversations of that type.

What To Wear Instead

“A statement bag is a much safer conversation piece. Avoid the messenger satchel, as it can look a little ‘2006 IT technician’. Instead, try a slick document holder with a smarter outfit or a small backpack for something more casual.” Giles Farnham, head of the River Island Style Studio

stylish bags for men

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Too Much Aftershave

We’ve all seen those TV ads featuring a man emerging from an asthma-inducing mist of body spray to be greeted by a hundred objects of desire. Who doesn’t want to believe that a heavy spritz of scent can have that effect?

However, too much is more likely to do the opposite and have your date coughing and spluttering as they run for the hills. Your date night grooming should be subtle. Overdoing it on the fragrance front also subconsciously says, “I couldn’t be bothered to shower, so I’m masking my musk”.

As we said earlier, don’t give them the chance to question your personal hygiene. After all, a first date is the time that you’re supposed to at least pretend that you’re a nice gentlemanly type.

What To Wear Instead

“You want your date to lean closer and catch a whisper of your fragrance, not sit there breathing through their mouth throughout. Choose a scent that you feel comfortable in and apply a spritz to either each wrist or bicep and one in the dip of each collarbone.”

British perfumer Roja Dove

the best fragrances to wear for a date

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Wooden Accessories

“Oh, how charming”, you think to yourself as you fasten your wooden watch. “She’ll think this is brilliantly quaint,” as your iPhone, safely encased in a whittled cover, is slipped into your trouser pocket. Wrong. So very wrong.

You know how we said that ironic T-shirts aren’t for first dates? Well, neither are pretentious accessories that pretend to be from a simpler time.

In a situation when everything you do will be over-analysed, you do not want to carry something that smacks of a desire to escape the present.

Ultimately, you don’t want to give the impression that after a few months of dating you’ll want to run away to the woods to hide from the world and get your whittling on.

What To Wear Instead

“Just as it pays to keep your clothing pared-back, wear only subtle accessories like a minimal watch or simple jewellery in classic colours and metals to avoid that bling-y look.”

Gordon Richardson, Topman creative director

men's accessories to wear on a first date

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