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Pros and Cons of Wearing a Hat on a Date

By Taylor James


Updated on

A lot of thought goes into what to wear to a date, especially if it’s a first date. In the age of dating apps, like Bumble and Tinder, you probably haven’t even met the person you’re about to go out with. In that case, your clothes and accessories are going to need to make a distinct first impression to leave your potential partner intrigued and wanting more. 

As frustrating as it is, there are no rules to dating. That means that dating decorum is really up to your individual interpretation. If you’re obsessing over what to wear, and you’re not sure whether you should wear a hat on your date, fret no more! Here are the pros and cons of wearing a hat on a date. 

Man and women on a date

Pro: Hats can give a glimpse into your personality. 

During the first couple of dates you have with a person, you’re still learning a lot about them. What’s their favorite food? Where did they grow up? What’s their personality? If you love wearing hats, because you enjoy fashion or have a creative personality, wearing a hat can help your date get to know you a little better.

A favorite ball cap on a casual date can be a great conversation starter. Who knows, you may have just found the person you’re going to catch the next ballgame with, and would have never known if you hadn’t worn your Cubs hat. 

Con: There’s a potential for hat hair. 

You may not end up wearing your hat for the entirety of the night, especially if you’re sitting inside at a nice restaurant. The risk of removing your hat is having some wild hat hair in front of your date. If you wear a hat, make sure you plan accordingly. Use extra hold hair spray, hydrate your hair with hair oil, or manage your locks with some gel. Make sure you bring a brush or comb, so you can pop off to the restroom and fix any stray hairs. 

Pro: A hat can augment your “flirt” game. 

During the Victorian Era, women used fans to flirt with their gentleman callers. If you showed up to a date with a fan, your date would probably think you’re pretty quirky, if not flat out weird. Ditch the fan, and flirt with your hat.

Hats add a level of mystery to your look. Where in the world is Carmen Sandiego? No clue, but her hat is awesome. If your date makes you blush, with just a tilt of your head, you can hide your facial expression making you more mysterious. A hat and some perfectly timed reactions can leave your date wanting to know more. 

Con: Wearing a hat could be a romance hazard. 

Say the date goes really well, and your new love interest goes in for a kiss. If you’re not careful, the bill or brim of your hat could get in the way of some smooching action. Make sure you take this into consideration, so you can sauvely take your hat off when you go in for the kiss. On the other hand, if you end up bonking your date on the forehead, it might be a “first kiss” story to tell your grandchildren. 

Pro: Your hat can help you get a second date. 

Hear me out. If you make it back to your date’s home—or even just to your date’s car—you can “accidently” leave your hat with your date. Need an excuse to text your date? Ask if you can meet up to grab the hat you left at their place. This almost guarantees a second meet up.

The risk you run is that your date doesn’t feel as strongly as you, and you never get your hat back, but that’s a risk worth taking in the game of love. Just don’t leave your Chapeau d’Amour.

About Taylor James

As Philip Treacy once said, “How a hat makes you feel is what a hat is all about.” And on that note, I hope you enjoy your hats and find the site useful. Learn more about Hat Realm's Editorial Process.