5 Stylish & Trendy Hats For Guys

February 13, 2009 by Anna   | Filed under Ask the Guys


Men have been sporting hats way before women. It was first used as protective headgear, then as a status symbol, and now more importantly as a fashion accessory. I love this because I don't think guys have enough accessories to choose from like women do. So I'm glad that a lot of guys are sporting the baseball hats regularly. But what if you want to venture into some cooler hats to top off your look? Well, lucky for you there are so many styles to choose from. Here are 5 of my favorites.

1. The Newsboy Cap
If a beret and a baseball hat had a baby, their love child would be a newsboy cap (also known as a Gatsby Cap.). This hat does not discriminate against age as it looks good on guys of all ages. Ashton Kutcher is looking very well put together here and I'm glad we're not seeing him with his usual trucker hats. His angular features offsets the roundness of the top of the hat and it compliments him perfectly. Go with a more dressed up look like Ashton did, or pair a newsboy cap with a casual t-shirt and jeans situation. It works with almost anything and everything.

ashton kutcher wearing a newsboy cap

Dress up your newsboy cap like Ashton Kutcher.


2. The Flat Cap 
The flat cap is very similar to the newsboy cap, but it's cleaner and more structured. It's as if someone couldn't figure out how to wear the beret, so they added a stiff brim to hold it in place. I am one of those people who find that berets can be annoying to fiddle around with, so I'm glad they came out with the flat hat that has more rhyme and reason to it. I love this style because it trends up any outfit and it is flattering on most face shapes. Brad Pitt is no exception. He looks very stylish wearing this flat cap, paired with a simple black tee and jacket. But what doesn't look good on Brad?

Brad Pitt looking very stylish with his flat cap.

Brad Pitt looking very stylish with his flat cap.


3. The Cowboy Hat
Some girls really like the John Wayne cowboy look. For me, a cowboy hat only looks hot without the cowboy boots and tight jeans. I know I use David Beckham a lot as an example, but he's just really good at this stuff isn't he? Anyhoo, I love the simple white tank and baggy jeans. I'm even liking the sling pack or murse he's wearing. The result: a very relaxed and effortless look. So if you feel like going for a more casual look, consider cowboy hats like these to complete your ensemble.

Pair a cowboy hat with a white tank and baggy jeans.

Pair a cowboy hat with a white tank and baggy jeans.


4. The Fedora Hat
I love the fedora hat when worn with just a t-shirt and jeans. If you were to wear it with a dressier outfit, it might look too much like a costume. With a simple t-shirt, jeans and some appropriate necklaces or leather bracelets, give yourself a more rocker look, as Johnny Depp so successfully shows off here. You should definitely add a fedora hat like this to your collection if you want to have more rustic and edgy style. It's the perfect accessory!

Johnny Depp knows how to wear a fedora.

Johnny Depp knows how to wear a fedora.


5. The Beanie
T.I. is looking very tough sporting the beanie in this pic. It's funny how the beanie started off as a dorky hat, made with felt and a propeller on top. It's now worn as a street look and the results are hot. Now I have seen the beanie worn on the red carpet by rockers and musicians, but they are the exception. I think this look is better paired with everyday wear. Note: Do not pull the beanie too low over your eyes as a driving precaution. Plus it just looks stupid.

He can do whatever he likes.

He can do whatever he likes.


10 Responses to “5 Stylish & Trendy Hats For Guys”
  1. MizzJ says:

    Great picks, all the guys here are perfect examples of how to wear these styles.

    MizzJ’s lastest blog post: Lust of the Week: 2001 Yves Saint Laurent Rive Gauche Dress

  2. Brigitte says:

    So true. And nothing beats a fedora hat.

  3. net-a-porter says:

    Any sports figure who succeeds at a early age seems to give up just being a kid. Maybe now she can just enjoy being herself. net-a-porterGood Luck!

  4. Purse says:

    I love fedora hats and I sometimes wear one. I think it’s very stylish and vintage

  5. halloween says:

    David Beckham in a cowboy hat is so handsome! He looks great in it. Maybe I’ll buy one too

  6. Alan says:

    Stylish and Timeless hats, excellent selection

  7. Bob Foley says:

    Dose anyone know who manufactures, and what style the Newsboy cap Ashton is wearing in the picture?

  8. Roger says:

    For four out of five of these hats you recommend either jeans or a t-shirt or both. Aren’t you ashamed? If a man wears a fedora (it’s called a fedora, not a fedora hat) with a t-shirt, he’s a douche.

    • Anna says:

      Nah, I’m not ashamed. Guys like jeans and tshirts and the article is about hats, not outfits. Everyone is entitled to their opinion. Thanks for letting me know your thoughts. I really appreciate it! :-) Have a wonderful 2011!

    • Jackie says:

      Lol I agree! I’m also very sick of trendy hipsters that wear fedoras with t-shirt and jeans and always thought they looked like a douche. Just because it’s in style it doesn’t mean it looks good on everyone. Johnny Depp can wear whatever he wants though, and to be honest, it doesn’t even look THAT good on him..

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