What To Wear On A First Date For Men

What To Wear On A First Date For Men

Knowing what to wear on a first date can be a difficult task for guys. You want your date to leave the rendez-vous thinking they don’t need to change anything about you — clothes included. Until the third date, that is, when who really lies behind that perfect hair, well-groomed face and impeccable style will surely come out. And by then it’s, well, too late.

“When it comes to impressing someone on a first date, its a very hard to work out what to wear,” says Dalton Graham, fashion blogger and founder of The Tailored Man. “There are two possible mistakes you can make; one is not dressing up enough or the other is overdressing.”

The consensus? Keep it smart casual. “Then, add a splash of a not-too-over-powering cologne and you’re on your way,” quips Graham.

Backing you all the way, here are the key pieces and tips for what to wear on a first date. Get it wrong and you’ll be finding yourself as a sorry contender on the next season of The Bachelorette.

Never Suit-&-Tie It… Banker Wanker

Yes, men look sharp in suits. But, a suit and tie — especially if it’s an office shirt-and-tie combo – can feel stuffy and gives the impression you’ve just come from work (and you’re career obsessed?), instead of taking the time to dress how you like, as a reflection of your personal style.  Ultimately, the goal on date night is to be at leisure, or at least appear like you’re having fun, says Dalton Graham, fashion blogger and founder of The Tailored Man.

“Opt for clean and simple,” says Graham. “And, don’t make the mistake of overdressing.”

So, if the date is in a fancy restaurant or the theatre, look to separates — a sharp blazer and tailored trouser – releasing the tie for the night from its shirt duties until Monday morning. A date is a different kind of business.

Shirt Flirt

A man who can cut an impressive silhouette in a button down shirt — one the simplest, yet striking fashion items — is worthy of a second date. From chambray to paisley to plain white, you can certainly play around with colour, textures and prints. But, two things are essential: fit and fabrication.

Ensure it’s a slim (never skinny) shirt so to enhance your physique, sitting square on the shoulders and draping naturally down toward the hips (leaving enough room for that dadbod paunch you may have accrued in your staying single). Then, it has to be cotton: breathable so to limit nervous sweats.

The button down shirt also solves the dilemma of not dressing up enough, says Graham, tucking it in and eschewing the belt — clean and simple.  “A crisp, white shirt is a must. For something extra, add a sweater.” Or a bomber jacket, adjusting the colour palette accordingly. Light tones for day, dark shades for night dates.

RELATED: Best Short Sleeve Shirts For Men

Keep ‘Em Keen, Jeans

The next piece in the first date outfit puzzle? “A nice pair of jeans or chino pants,” says Graham. Or a combination of the two. Opt for a pair of denim jeans, but in a trouser fit. Look to a straight cut: roomy in the thigh like pants but with a tapered leg from the knee down. A cropped ankled is a contemporary look or simply roll the cuff, which gives a nice colour contrast in you’ve gone for a selvedge, dark denim with white interface.

A 10-12 oz. denim is the ideal fabric: weighty enough to drape light a trouser but not so heavy that it’s bulky and stiff. A light, vintage wash jean is a fresh shade for summer and daytime dates, pairing whatever denim colour you choose with a cotton shirt – tee or long sleeve. Then, roll the sleeves. Sprezzy, done right.

Seal The Deal

What you put on your feet has never been so important. “This, of course, depends on where the first date is,” says Graham. “Either a nice clean white sneaker or a boot classic like the R.M. Williams chelsea.”

Basically, your shoe has the power to give and take away from your outfit. A sneaker will dress down the formalities of separates or a shirt and trouser combination, while leather boots or a dress shoe — from monk to derby brogue — will lift the leisurely nature of a jean, t-shirt and sweater outfit.

When selecting shoes, adhere to dress codes first, which is linked to the venue of the date. Follow with overall aesthetic — matching your trousers to your shoes — and then go for comfort. Don’t break in new leather shoes of your first date. Limping, because of blisters, isn’t attractive.

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A Smackeral Of Cologne

How To Apply Cologne

You want to be remembered for the right reasons, right? Well don’t be the guy who bathes in Aqua Di Gio before his date and wonders why he never hears back from the date. Opts for a modern and suitably unique cologne that will create interest but not assault the nose.

First Date Outfit Ideas FAQ


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