Well done! YOU are the MAN! You’ve finally got a date with that special someone you’ve been eyeing for 10 (billion) months. But can you wear your favorite hat for the occasion? And should you?
First impressions matter- so unless your date is in a place that warrants wearing a hat (i.e. the sunny outdoors), then do NOT wear one. You want your date to think you took the time to dress up, at least a little.
But I get it, you’re a man who enjoys to don atop his crown, that of what makes YOU feel confident…like a king. And confidence IS king.
And so there are certain situations where wearing a hat won’t seem out of place…
Where is it acceptable to wear a hat on a date? (guidelines)
First off in these certain situations, I should mention, me (and most other women I’ve asked) would argue AGAINST wearing a hat to begin with (at least where first dates are concerned)- however, I know you’re a stubborn SOB, so if your date happens to be within these areas, then it should be okay.
First date locations/guidelines:
- Park dates (and ONLY if the date is that of a casual one)
- Extremely sunny locations and ONLY in the daytime (beach dates/ desert areas)
- Anything of a casual nature in general (coffee dates/ zoo dates/trekking and or “active adventure” dates.)
When is it NOT acceptable to wear a hat on a first date
- Fancy dining (or anything indoors.)
- At night
- Any situation or environment that requires you to dress up in something more than jeans and/or sneakers.
- Or just don’t wear one- how bout that? (Ignore my inner voice, he’s a stubborn SOB too.)
Best types of hats to wear on first dates?
Baseball hats
Try not to wear one too strained or “rough looking”. At the very most you want to look like a scruffy man with a slightly disheveled look (that you seemingly did on purpose.)
However, you don’t want to look like a hick who just came trudging through life on horseback (no offense to hicks.)
That’s it, this is literally your only hat option (where first dates are concerned) that won’t make you look too “douchey” and/or try-hard when wearing one.
Forgive me, dear readers, this is not me being mean, this is just the likely outcome that awaits you, as most (on first dates) will think this way too.
Worried about what to bring on the date? Check out this secret list I made to guarantee you’re prepared for everything!
What does the opposite sex think of hats on first dates?
Now I know you don’t believe your boi just yet, and so I sought after a poll on Reddit asking the very same thing. Below are some of the responses.
As you can tell, just because you CAN wear hats on some occasions (even during a first date, if you must), not all hats are preferable.
Not to say you must always concede to public opinion, but this is the first date after all, and so you want to try to not be totally controversial just yet.
Some more responses from Reddit:
As I said, most hats are a big no-no, whether that’s my opinion or the opinion of others. No one wants to share breadsticks with Freddy Kruger, a nightmarish of a situation that would be (okay I’ll stop.)
What types of hats to always avoid on first dates?
As highlighted in the Reddit forums, NO fedoras. This kid looks adorable in it- you for sure won’t.
No cowboy hats either- really anything ostentatious that makes you look too much like a try-hard.
Subtlety loud, bois. That is the way to go, almost always.
Sayin a lot without saying much at all- a good style mantra to follow. Take it from the future Mars King himself, he gets it.
What does wearing a hat on a first date actually convey?
Wearing a hat on a first date can signal many things (like you saw in the Reddit comments.) In an even mildly romantic setting, the presence of a hat can brood an umpteenth amount of preconceptions, from within the mind of your gorgeous date:
What your date may think of you when wearing a hat:
“What’s he/she hiding?”
“Does he/she not care about this date?”
“I came dressed up, it seems like he/she didn’t even put in any effort.”
It may not seem fair, or just (even if you simply like wearing hats), but unfortunately – these are the types of thoughts that will likely plague your date’s mind (guy or girl).
Can anyone pull off wearing a hat on a first date?
There are guy’s who can pull off the hat look on first dates (and really whenever they damn well please.)
But you ain’t Michael Jackson, and this ain’t Moonwalker (1988), so don’t even try. It takes a certain caliber of man to pull off this look (especially on a first date), and if you aren’t already the most confident bloke out on the town that night -then your date will see that, hat or no hat.
Wearing a hat will just make your failed night even worse.
Wear what you want, but heed some caution
Same rule applies with wearing your hat backwards, you can do it, but heed a healthy helping of caution before you do- as it’s more commonly considered a “non grata” (unwelcome) look.
As mentioned in a previous post on “What to wear with the color yellow“, I discussed how at the end of the day, it all boils down to one thing…confidence. Wear whatever you want, however, know your limitations by what will be easier, or harder to pull off (stylistically speaking.)
And on a first date, how much harder do you want to make it for yourself?
What about balding men? Hat-fishing?
Firstly what is “hatfishing”?
“Hatfishing” is when someone (usually on a dating site) wears a hat in all their pictures or dates to conceal that they are balding and/or bald.
Don’t be a “hatfisher”, gentlemen, it’s unbecoming.
“But I’m insecure about my hairline/lack thereof, Dom!”
Exactly!
The problems with wearing hats on dates for haired and non-haired individuals isn’t the lie of omission, everybody lies a little on dates- rather it’s the way wearing a hat can come across.
First dates are special (at least a little), so go at it with some gravitas.
“First dates” are the Premier League, the NBA championship, the World Series. They’re a self-contained microcosm of an event, whereby the actions you take on that day- and in what manner of fashion you take them in- will bear of greater consequential importance to you, compared to your average day (when you have no date.)
First dates are events where it’s customary to show yourself in your best light-at least if you care enough about getting that second date.
Not to hype “first dates” up too much, but you get my point. They’re a little more special, thus that should warrant a little more effort, from both parties.
If you need to buy some clothes for your date, hold up a sec. I wrote an in-depth list of the top places to buy men’s clothing on a budget which I encourage you to read!
The confidence factor
People respond to confidence, regardless of anything else at first glance. Wearing a hat will more often than not make you seem overly self-conscious, insecure, and timid.
If you’re bald, the harsh truth is your better off owning what you got. Embrace your look, as well as there are ways to “facilitate” the problem a little (such as shaving your head completely-embracing your inner Jason Statham for example.)
Plus if the date goes well, the hat will have to come off eventually, what then?
If you are worried about sweating on your date, check out this article I wrote on what colors HIDE sweat the best!
“He’s the kind of guy he walks into the room his d*** has already been there for two minutes.”
-Moneyball (2011)
Like I mentioned at the beginning (and throughout this post), confidence is king. Wearing a hat on a first date will almost always give off the wrong impression.
You want to be the man who walks into a room with a sly smirk on his face, knowing a secret that everyone else knows you know, and wants to know too. That’s confidence.
First dates are nerve-wracking, for both parties, people are on edge. They’ll notice more things (about everything) during those first few hours with you, then they would on an average day.
Don’t give yourself a reason to stick out in a negative light. Once they get to know how much of an awesome stud you are, then you should have more leeway to “experiment” with your style choices.
Stay Rogue.
