Dappered

Affordable Men's Style

  • Don’t Miss Anything
  • Start Here
  • Essentials Shop
  • Latest Deals
  • Style Scenarios
  • Reviews

Do women like men in baseball hats?

October 14, 2010 By Joe | Heads up: Buying via our links results in us getting a commission (not always, but just about), which helps keep the lights on around here. We also take your privacy rights seriously. Head here to learn more.

Ask A Woman: What do women think of guys who always wear a ball cap?

If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. And don’t worry, your identity will be protected too. Click here to get to know Beth, then get in touch with her by sending your question to: askawoman@dappered.com
.
—
Hi Beth:

I’m 35 and a guy I’ve been hanging out with since college wears a baseball hat every time he steps out of his house.  He even wears it to work even though he works inside an office.  It’s a really casual place so he’s not getting in any trouble, but I tell him women just don’t take guys seriously who wear hats all the time.  He says he likes his hats and women tell him he looks “cute” in them. Who’s right?

– Andrew


Hi Andrew,

As with all things, whether or not baseball hats look good depends on where you wear them, who you’re with, what the occasion is, and so forth.  If you live a casual life–your work environment permits casual wear, and your hobbies require casual wear, and the company you keep dresses casually–then a baseball hat is appropriate.  And also monotonous, safe, and liable to induce narcolepsy.

The biggest issue I see with baseball hats is that they limit what you wear on the rest of your body.  You’re not going to wear a baseball hat with a sharp blazer or a button-down shirt; you won’t wear a baseball hat with fine shoes or pressed pants.  If you’re wearing a baseball hat every single day, you are probably living in jeans, sweats, and tennis shoes, which is…BORING.  Maybe your friend doesn’t care about style…in fact I’d wager a good amount of money that he doesn’t care about style, which is fine.  We don’t judge here.  Well, I do, of course, but that’s why I’m paid the big bucks.

As to whether women will take him “seriously”…I think women’s feelings on baseball hats vary in ways that their feelings on, say, clean underwear and cockroaches in the bathroom, don’t.  A woman who herself dresses very casually and prefers an evening at Buffalo Wild Wings to a night of stiletto heels and martini-tasting will likely find a man in a baseball hat to be a good match for her.  Now if your friend is wearing his hat to wine bars during happy hour and then wondering why none of the professionally-dressed women are interested in him, he needs to either adjust his expectations or take that thing off his head.

Beth

Got a question for Beth? Send them to: askawoman@dappered.com

Editor’s Note:
Baseball hats also recently came up in our “growing up your style” feature.  To read that, click on over here.  And what’s your take?  Do you wear baseball hats?  When?  And for the record, this is one baseball hat I think any guy who’s ever seen “The Natural” would love to wear:

J.Crew at ShopStyle

Filed Under: Accessories, Clothing, Women Tagged With: Ask A Woman, baseball cap, baseball hat, baseball hat addicts, hat from the natural, the natural

Continue the Conversation …

Want to share your thoughts on this article? Send us a tweet, join the discussion on Facebook, or hit us up on Instagram!

Don’t Miss Anything

Subscribe via email to get articles in your inbox or add Dappered on Flipboard. You can also follow us on Twitter, Facebook, and Instagram. Or subscribe to push notifications to get alerts immediately.

New Here?

Well, welcome to Dappered. Here are what we consider the most useful posts on the site if you're looking to put a little more effort into your appearance. Just want to see our favorite menswear products? Shop our essentials here.

Long Weekend Men’s Sales Roundup – 2023 Unofficial Start of Summer Edition

Long Weekend Men’s Sales Roundup – 2023 Unofficial Start of Summer Edition

25% off Bonobos. Target 20% off select (including a polopalooza winner.) 30% off BR. Grant Stone, Rhone, adidas, and $248 off the Billy Reid Bond Peacoat. Updated for the weekend.

J. Crew: 40% off Long Weekend Sale (new arrivals too)

J. Crew: 40% off Long Weekend Sale (new arrivals too)

Stretch chino shorts. Irish linen shirts. New sunglasses, camp mocs, seersucker short sleeve button downs, and more.

Repair, Don’t Replace – Getting Your Goodyear Welted Shoes Resoled

Repair, Don’t Replace – Getting Your Goodyear Welted Shoes Resoled

What’s worth it, when to do it, and what to expect when you’re getting your welted shoes fixed, recrafted, etc.

Follow Dappered on Instagram »

Men’s Fashion or Affordable Style?

Men's Fashion or Affordable Style?

Fashion is temporary and expensive. Style is timeless and affordable. Dappered® helps you work the retail system so that you can be comfortable, look sharp, and save money.

Want to share a great product? Email Us.
For a fit perspective, see Joe's measurements.
Make sure to read our affiliate disclosure.

CONNECT WITH DAPPERED

Thanks! Check your inbox or spam folder to confirm your subscription.

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter

Most Popular on Dappered

  • Long Weekend Men’s Sales Roundup – 2023 Unofficial Start of Summer Edition
  • J. Crew: 40% off Long Weekend Sale (new arrivals too)
  • Repair, Don’t Replace – Getting Your Goodyear Welted Shoes Resoled
  • The Dappered Space: Most Wanted Affordable Home Style May 2023
  • Monday Men’s Sales Tripod – REI Anniversary Sale, Gustin’s CXL Briefcase, & More
  • The Best Affordable Watches for Grads or Dads of 2023

Popular Topics

  • Best dress shirts to own
  • Best looking watches under $100
  • Best men’s dress shoes under $200
  • Nike Killshot sneaker alternatives
  • How to wear a suit without a tie
  • Suitsupply store review
  • Suitsupply Blue Line review
  • J. Crew Factory Thompson suit review
  • How much does it cost to tailor a suit?
  • Dopp kit essentials
  • Brown shoes with gray pants
  • Men’s style buying guide

Copyright © 2023 Dappered.com | Dappered, LLC | Dappered® is a registered trademark of Dappered, LLC

Hat tip: Magazine Pro Theme On Genesis Framework

Dappered does not collect or sell its users personal information | Disclosures: Privacy and Affiliates, Gilt.com, FTC

WPE

We work with partners that use cookies to understand how visitors use our site. Find out more.