Real Men Talk: What Should A Man Wear On A First Date?

Let’s get real: how many times has any article from a women’s publication talked about what men should wear on a first date? Or, how many times has a men’s publication covered this topic without actually including the voices of gay men?

Lately, I’ve been inspired to bring this conversation here as I realize that most dating articles are heteronormative by nature. Not only does it alienate LGBTs, I also realize that as a journalist, I aim to prioritize the value of every man’s opinion regardless of sexual orientation.

Further continuing the conversation about date dressing, I’ve decided to moderate my first discussion featuring six smart and sexy men. The participants are: Henry of Street Style Poser (go check out his blog!); Brandon Hudson (vocalist) and Brennan Benko (drums) of L.A.’s hottest band The Heirs;  Marcus (a journalist who pumps out super awesome thinkpieces on Medium); Eric Ford (a content coordinator with an eye for style); Malcolm (an analyst who ain’t your regular corporate bro).

Given the diversity of their lifestyles, backgrounds and occupations, everyone’s responses are unfiltered, insightful and refreshingly witty.

A) What should a man wear on a first date?

“It really depends where the date is, but the outfit needs to say casual chic with a hint of chivalry and flirty fun. A button up shirt with the first two buttons undone, fitted jeans or chinos and a bomber jacket if the weather allows. Clean sneakers or casual dress shoes [are needed] to finish the look. That sounds like a cliche look, but you don’t want to be dressed better than your date nor do you want to bore her/him either.” – Henry

“A man’s date show[s] [how he should] dictate his outfit. For the flow of where you are trying to go. If it’s casual, be casual. If it’s formal, be formal. Dress for the occasion. Don’t do too much and don’t be underwhelming. Find a middle.” – Eric

“I think it’s all about being the cleanest version of yourself. Like, you don’t want to dress like someone you’re not. But, don’t be a slob. It’s still like a job interview. So, if you’re into punk rock or DIY projects, wear your nicest ripped jeans and a freshly washed vintage tee.” – Malcolm

“I’d probably stick to what I know. I’ve always been into silky patterned [shirts] – almost a bit oversized long sleeve button ups. They just make me feel a bit more classy in the evenings. I like trousers over jeans as well. I dunno, I think the season depends. Jackets are cool in the winter. Leather jackets are the go-to.” – Brandon

“At some point or another, a suit is always a classic look. That being said, it completely depends on what the date is (where you’re going, what you’re doing, etc.) I don’t often go on dates that require a lot of formal attire. So, more often than not the ideal outfit is simply whatever I feel the most confident in at the time.” – Brennan

“Something classic. Button up shirt, jeans, white sneakers [and] a great jacket.” – Marcus

B) Let’s say that he just finished work; however, he has no time to change after wrapping up a 9 to 5 shift (whether it’s a start up, food delivery gig or regular office job). What is the one transitional piece that every man should keep in his closet? 

“A different outer coat. A sloppy zip up or a matching suit jacket both scream ‘I came from work!’ But, if you wear something fashionable that matches your work clothes, it shows some effort and looks good.”-  Malcolm

“Definitely something comfy I could wear all day long. A T-shirt and jeans combo is great because I can easily transition from work to date mode with different jackets.” – Marcus

“These pieces always depend on your job. In a more relaxed setting, make sure your shoes are able to go night and day. For a more business formal work environment, it’s better to substitute and bring a new pair of pants with you or at least make sure your suit is able to flow from night and day. Don’t be afraid to change clothes. that’s what they are for.” – Eric

Is a suit too fancy for a date at a bar?

“For me, sure. But, that’s not my style. I think age also plays a role. Younger people are all about chasing trends. Hey, older singles are all about chasing stability and the inbetweeners are a mix. So, a suit can project success and stability, but you gotta back it up. But, if you’re 24, maybe it’s a sign of insecurity.” –  Malcolm

C) Is it OK to wear athleisure? 

“Athleisure is so taboo now. It’s amazing how you can flex it with multiple pieces of other styles. I definitely utilize it correctly, possible in a shoe or top.” – Eric

“Ummm, yes, but not [on] a first date lol.” – Malcolm

“I’m not against athleisure. I like guys who are laid back and feel comfortable in what they’re wearing. Just not to the point that they look as if they’re on their way to a sports meet.” – Marcus

D) Are mandals ever appropriate?

“Preferably not on a first date. Subsequently, if we were hanging during the day at a cafe or somewhere else outdoorsy, sure. I would wear sandals, too.” – Marcus

“For a date, I would always steer clear of open toed shoes…Definitely not something I think is the most appropriate when there’s any formality involved. If you’re going to the beach, then go for it.” – Brennan

“If your date is relaxed, maybe at a beach or park, go for it!” – Eric

“The problem with sandals is not many guys can actually pull them off unless you’re intentionally going for the unfashionable look. But, I don’t see why you would jeopardize that first date.” – Henry

If he wants to wear sandals, what can he style it with?

“If you insist on wearing sandals to a date, style them with chinos or semi-casual pants. No shorts, no socks. Don’t be hopeful for a second date though unless your date has toe fetish.” – Henry

E) For men who want to experiment with different silhouettes (e.g. tighter fits) and bolder colors (or prints), what’s the one type of garment that can work on a first date?’ 

“Hmmm, I’d say start with simpler colors/tones if you’re trying out new patterns. Blacks and whites always blend in no matter how intense the print or graphic is over it. Also, try shit on. That’ll really open your mind up to the possibilities. I’ve realized over this year that I like reds and blues on me, but it took the initial push to try or else, I probably would’ve just went for the usual palettes.” – Brandon

“Your pants fit is important. Fitted/tight pants are amazing, but make sure they are your size. Bolder colors don’t always mean bright. Just something that stands out so [I’d go for] like reds, yellows [and/or] orange are great. Just make sure it flows!” – Eric

F) How much skin should he reveal? 

“Haha…hmmmm, enough to get you a second date. But, not too much that it’ll get you removed from Instagram.” – Henry

“As much skin as you want. It’s your date. You set the rules. As long as it flows with your date, do it. A first date is what you make it – there are no rules!” – Eric

“[I] don’t think showing a little chest with a button down is ever a problem. But, I would avoid wearing tank tops/shorts on a first date.” – Brennan

“I don’t know, I’m kind of in between. I don’t usually button my shirts up all the way and I don’t unbutton all the way down to my belly button either. I think moderation is good. Find a good, comfortable place in the middle I guess. Don’t be douchey haha.” – Brandon

If a man has tattoos, what type of shirt should he wear on a first date? 

“I have a decent amount of tattoos on my arms and I’ve never based any of my attire around covering them. I don’t think having tattoos should ever be something you have to cover up or hide on a date. If you’ve got tattoos, then they’re on your skin whether you like ’em or not. So, wear them with confidence!” – Brennan

“I personally don’t think it really matters anymore to hide them. We live in such a progressive time. Be yourself and have fun.” – Brandon

G) What’s the one thing a man should never wear on a first date? 

“Flip flops.” – Brandon

“They shouldn’t be experiment if they’re not used to dressing up. Sticking to modern menswear pieces (button up shirt, jeans and sneakers) is always a good idea, especially for first dates. It shows they cared about the date. Nothing obscene or ill-fitting, please.” – Marcus

“Crocs.” – Brennan

“Crocs. I don’t think shorts should be worn on the first date either, unless your legs are the sexiest part of the body.” – Henry

H) Do you feel that men dress differently in front of women vs. being in front of other men? 

“I think we all go through a position where we try to figure out what is acceptable in all occasions. Even at times, I struggle to make sure what I am wearing fits the area and people I will be around. I’m learning the more you accept who you are, the more you accept your closet, the more you can be comfortable to be yourself in front of men or women no matter the outfit!” – Eric

“I’m not sure if there’s a difference and if there were, it’ll be subtle. I imagine guys would want to make a great impression on a first date so they will put in the effort regardless if the date is a man or woman.” – Henry

I) If a man wants to wear a garment that can work at all settings (sporting event, museum/art gallery, concert, fancy restaurant, bar, etc.), what should he buy? 

“Cologne; a gold chain.” – Brandon

“A gray Thom Browne fitted suit. You probably won’t be able to dance in it at a concert, but you’ll no doubt be getting lots of flirty eye-fucking.” – Henry

“Gonna agree with Brandon on this one. Always make sure you’re smellin’ nice. And a couple of cool pieces of jewelry that are important to you are never a bad addition. Also, wear your favorite pair of socks. Keep your toes happy.” – Brennan

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Michelle Varinata

Lapis - (n.) a layer Shrek once said that "onions have layers" as he was peeling one. Like an onion, I have layers. Born in Jakarta and raised in Singapore, I grew up being surrounded in a multicultural environment. Then, I moved to the States, where I lived in NYC and L.A. The creativity, hustle, bustle and vibe of those cities inspired me to become a blogger, journalist and influencer. Writing by day and living it up by night, I slay in the streets one OOTD at a time. Full-face makeup included, too. ;)

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