In the modified words of Lana Del Rey ‘every now and then the stars align, boy and boy meet by the great design’, and perhaps this particular date will show the two of you that you just might be the lucky ones. Now, when it comes to first dates, before we move on to outfits and style choices, let’s cover some basics. First of all, this person is already kind of into you – hence the arrangement for the date, so all you have to do is be the person you were when you met – whether it was in a club, a coffee shop or a dating app. Don’t change anything about your attitude and personality. It may sound a tad cliché, but it’s true – if it works out with this person, then it should work based on how you present yourself on that first date – completely authentic with zero pretending and embellishing. Of course, keep certain topics off the table – don’t tell them your entire life story, keep it light and fun and make sure you charm their socks off and get that second date. Ok, now that that’s covered, let’s move on to the style section. While you shouldn’t wear something that is totally not your style in order to impress someone, appearances matter, so make an effort to at least elevate your current style and not show up in a sweatshirt and an old tee. If things work out, there will be plenty of opportunities for him to see you in attire that’s relaxed, so let’s take things up a notch for the occasion. We have multiple date scenarios lined up and the perfect outfits for all of them, so find what yours is and dress accordingly.

Casual movie night

In case you’ve agreed on a low-key and classic movie date, your clothes should reflect that. A simple (newer and freshly ironed) tee will do, and if you’re into graphic or slogan tees, especially those that have something to do with your interests, all the better, because you’ll have a great conversation starter. For this occasion, it’s time to bust out that pair of jeans that makes you look your best, and in case you think it might get chilly, bring a cardigan if you’re into them – the preppy style is totally back and you can rock it. If, on the other hand, they’re really not your thing, a leather jacket is a foolproof piece as it looks sexy on everyone, so even if you have flaws, the jacket is there to make up for them. This is effortless low-key at its finest and he’ll definitely be into it.

Taking the traditional route

Perhaps you’re an old fashioned gay guy who believes that a real date constitutes dinner at a nice restaurant, and that’s totally fine – old time romance is never a bad route, especially if your date was into it when you suggested it. Now, most restaurants have a relaxed dress code in the sense that you can get away with a nice white or even narrow-striped button-up and a pair of chinos with cute loafers, but if you have a thing for great men’s suits, don’t be afraid of looking like you’re trying to impress someone. If you love suits, you rock them, and if your date asks you why you’ve gone ‘all out’ just nonchalantly tell him this is how you normally dress most of the time. Suits draw people in like a moth to a flame, so even if he makes a joke about it, don’t worry, deep down he’s actually completely slayed and smitten.


So, you both have a thing for dancing till dawn and your mutual notion of what constitutes a rocking first date is going to a club. This type of date can get really hot really fast, especially with all the dancing and the drinks. When it comes to clubbing, you definitely want to go somewhere between the dinner and the movie date – not too casual but not too dressy. Wear comfortable pants that will make the dancing part easy and won’t hold you back. Cotton twill pants (roll them up a bit for a little more pizzaz) in your go-to color give you plenty of movement and look super sexy in that effortless kind of way, and the best part is – they look amazing on everyone regardless of how you’re built. Now, this is where you go with a sleek pair of tennis shoes – they can be white or in color – totally your call, just make sure the color of the pants and the sneakers get along. For instance, blue twill pants and white classic Adidas go great together. When it comes to tops, you can go with a fitted tee in a color that complements you and shows off your bod, or dress it up a little with a shirt, but make sure you roll up the sleeves for that slightly casual effect. Make sure the shirt isn’t too fitted as it might get in the way of your moves on the dancefloor.

Peter is a gay lifestyle writer at Queer Voices magazine. Follow Peter on Twitter for more tips.