What Gay Men Should Wear First Date

Gay Dating

What Gay Men Should Wear on a First Date

Sam Stieler

Written by: Sam Stieler

Sam Stieler

Sam has been writing about dating and relationships for more than three years now. He holds a bachelor's degree from Bucknell University, has self-published a few of his own books and is currently working on mastering the double right turn in his salsa dancing classes.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Going on a first date with a man you really like can be pretty nerve-racking. Not only are you going to worry about those largely uncontrollable elements of your first date (whether you two will share good conversation, whether you’re compatible, whether things will go the way you want them to), you will also find yourself stressing out endlessly about all those little things you do have control of.

And few of these controllable elements are going to cause you more stress than what you’re going to wear on your first date. Well, if you keep the following points in mind, you will always look appropriate and feel confident on all of your first dates.

1. Take care of large grooming actions days before.  

  • You know how your hair usually looks a little funny after you’ve gotten it cut?
  • You know how a lot of guys look better with a little bit of stubble?
  • You know how going tanning can look a little overdone for a couple hours?

Instead of taking care of these big grooming actions the day of your date, get them done a couple days ahead of time so they look their best right in time for your date with a new guy.


“You will botch any chance you have with your

date if you’re constantly adjusting your clothes.”

2. Take care of little grooming actions right before.

Shower and style your hair right before your date. Brush your teeth and eat a mint right before your date. Put on deodorant and cologne right before your date.

All of these little grooming actions wear off in a short period of time, which means if you performed them first thing in the morning, they will wear off just before you grab after-work drinks with your date.

3. Dress as he remembers you.

Wear a look composed of clothes similar to what you were wearing the first time you met your date. The very fact you’re on a first date with him proves he found the way you normally dress attractive, or at the least attractive enough to peak his interest.

Is it possible he would find you more attractive if you dressed another way? Sure, it’s possible, but rather than rolling the dice, stick with what you know works.

4. Wear your “power clothes.”

How you dress on your first date has more to do with how those clothes make you feel, and less to do with how those clothes make you look.

  • Should you wear clothes that make you look good? Of course.
  • Should you wear clothes that highlight your best features? Absolutely.
  • Should you put together an outfit any man would drool over? Yes!
  • But should you wear clothes that make you feel silly, physically uncomfortable, or less than your best self? Never.

No matter how good you look on a date, you will botch any chance you have with your date if you’re constantly fidgeting, adjusting your clothes or feeling self-conscious.

Because ultimately, even with men being highly visual creatures, no man is going to feel great on a date with you if you seem to be having a very bad time due to making a couple unfortunate wardrobe choices.

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