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Men, What to Wear on a First Date to Get A Second One

You’ve 10 minutes to go until you’re meeting a Bumble date. You’re still staring hopelessly into your closet, trying to find the fit that will leave your date thinking about how damn good you looked well after you’ve parted ways for the night. It’s a balancing act. You want to flex your best pieces without looking pretentious - or worse: overdressed.

It’s painfully easy to get wrong when failing to bear the right details in mind. I’m sure you’ve been told: “Just dress like yourself!” or “Wear what you usually wear.” I’m here to tell you that’s just not good enough, kiddo. We live in a world where image is more important than substance (unfortunately). So no matter how deep you think your personality is, if you look shallow or boring *shrugs* you might as well be.

“So Mr. Related, how does a guy nail the first date style?” I’m glad you asked, dear reader. The first and most obvious detail should come naturally to the style connoisseur and layman alike, but I will include it anyway:

Where are you, and where are you going?

You simply must adhere to the conditions of the climate and also the code of your destination. A date at King Cole Bar in Hell’s Kitchen NYC at the peak of winter is going to look a hell of a lot different than a date in LA at EP&LP on La Cienega in August. If you can’t dress for the climate, you obviously can’t handle a relationship. Take what is appropriate for the weather and your venue, then get to work.

The Classic Whiskey Bar

The Walker Inn

The Walker Inn - Koreatown, Los Angeles

Nothing beats a neat whiskey in my book. Wear your favorite biker jacket, a Steve McQueen approved sweater, blue jeans and suede chelsea boots. It'll have classic vibes without being stuffy or old-fashioned. If it’s too hot for a sweater, a white T will do just fine, with the jacket slung over the shoulder.


The Fancy Joint

Beauty & Essex Hollywood

Beauty and Essex, Hollywood

Okay then, Mr. Moneybags, you’re taking your date on a cultural extravaganza are you? Make sure you dress the part. To start, for the love of God, do not wear a black suit. Navy is always a good choice, but you can do better. A blue velvet blazer is the ultimate wingman. Elegant and OG, plus the luxe velvet will give your date even more of an incentive to take your arm. Pair it with a white button up and a solid pink tie to lighten yourself up, or with a black turtleneck for a more elevated look.


The Popular Place

The Highlight Room

The Highlight Room, Hollywood

You usually can’t go wrong picking one of the hottest places in town. Before we get to the fashion advice, I’d recommend scheduling your date around the peak hours. Nothing is worse than trying to have a conversation while yelling over house music and bachelorette parties. You have a lot of options in a place like this. Black Chuck Taylors, light wash jeans, a denim button up and a bomber jacket will make do. Be sure to throw in some man-jewelry or even a bandana hanging off your belt loop.

The Club


The Avalon, Hollywood

Not sure why you thought this was a good idea, but whatever. It’s gonna be a mess of bodies full of booze in there, so don’t wear light colors - unless you want to show off all the stains you’ll inevitably get on yourself. It’ll get hot too, so wear layers that are easy to shed as the night goes on. Frankly, I’d just go somewhere else.


Afterwards . . .

If it’s that kind of date, then you’d better be sure you’re underfit is on point. You know where to get the best underwear and socks from, so now it’s just time to find the one that fits your style.

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