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A Men’s Style Guide for the First Date

men, sitting, coffee, outside, date, friends, lgbt, masculinity, masculine

Guest Contributor

Once you’ve picked out the venue, you’ll have to decide what you’ll wear on your date. We’ve got a style guide just for you, gents. Listen up!


You’ve landed a date with person of your dreams, lucky you. After you’ve figured out where you’ll be going, you’ve got to think about what you’re going to wear.

This may sound like a bit of a trivial thing, but you’d be surprised how many people will be put off by their date’s outfit; but this is why I’m here to help, I’m going to tell you the do’s and don’ts of dating style so you can have a stress-free date.

The first thing you have to think about is where you’re actually going as you’ll need to dress appropriately for the venue. If you’re off somewhere that’s a little more low-key, then you don’t want to turn up in a full tuxedo and tie; the same goes if you’re off somewhere a little more fancy, you don’t want to turn up in a pair of jeans and a T-shirt.

woman, beer, fun, date, barPub or Bar Date

Probably the most common dating spot for many a young couple is the classic pub or bar. Now, with a pub or bar date you’re generally going to wear something a little more casual, but don’t wear baggy or scruffy jeans with a graphic print t-shirt, this makes you look like a teenager who has no idea what he’s doing.

Instead, opt for something smart, but not too smart; I know it sounds like I’m sending you mixed messages, but hear me out. You’ll want to wear something that’s appropriate, smart, yet still casual enough to still keep you stylish. This is where you enter the smart casual territory, a difficult nut to crack with many men, but with a few tips and tricks, you’ll grasp it in no time.

Let’s start with the shirt. You’ll want to go for something classic and simple, yet not too formal so it looks like a shirt you’d wear to work. Go for a plain white oxford shirt and leave it untucked, as tucking it in will add that little bit of formality that you don’t need.

For your bottom half, again, you’ll want to go for something casual, but smart enough to be appropriate for a date. Try wearing a pair of casual trousers, or even a pair of chinos as the relaxed fit and material of the trousers is casual enough to be appropriate for a pub or bar. Depending on what time of day you go, you’ll want to color coordinate accordingly. If you’re going during the day then opt for a lighter color like stone or beige, but if you’re going at night, go for a darker pair such as navy or black.

If you’re thinking trousers or chinos may be a little too formal, you can always opt for a pair of raw denim jeans. Raw denim is a great alternative to black or even blue jeans as they’re dark enough to work for a smarter occasion, yet still casual to wear on a date.

Now on to the footwear, this is somewhere many men fall flat, but have no fear, I’m here to tell you how to pull it off. As a rule, I’d avoid trainers, as they can look a bit scruffy, but if you grab yourself a pair that are sleek and stylish you can get away with it.

If you do want to wear something a little smarter, go for a pair of loafers as these will give you a stylish and sleek look no matter what the occasion. You may be thinking that they’re a little too formal, but the great thing about loafers is that they can be worn in both formal and casual occasions with ease.

Dinner or Restaurant Date

If you’re off on a dinner or restaurant date, you’ll want to wear something a little smarter, as you’ll want to be appropriate for the restaurant, so go all out and dress to the nines. Of course, this depends on the restaurant you’re going to, as certain places will have dress codes that you’ll have to adhere to.

Go for a suit! Some of you may be thinking that a suit is a little too formal, but if you downplay it a little bit, you can have a great look that’s classic, smart, and stylish. Try wear a navy or a dark grey suit as these are classic colors that you can’t go wrong with.

The great thing about these colored suits is you can pair whatever colored shirt you like with them. But, if you’re going for a grey suit then I’d stick to a classic white shirt, whereas, if you’re going for the navy option, then you can still stick with white, but you can also venture into the pink or a light blue shirt territory.

For your shoes you’ll want to have a pair that match with your suit, and by this I mean a formal pair. Go for a classic brogue or monk strap shoe to seal the deal. Again, the color matters, with a grey suit stick to a black pair, whereas with the navy suit, you’ll want to opt for a brown pair.

So there you have it, a few simple tips and tricks to get your through your date with ease. Just remember you have to think of where you’re going first, as you don’t want to be overdressed or underdressed.

Avoid graphic T-shirts, or a T-shirt of any kind really, as you want to make an impression, and no scruffy jeans! That’s a rule I’m adamant on.


About the Author

alex outlawAlex Outlaw is the co-founder of a men’s fashion store called TheIdleMan.com. Not only does he manage all the marketing but he also writes for the sites fashion blog called the Manual and runs their instagram, twitter and facebook accounts.

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