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Preston Konrad

Professional Fashion Expert

Hats For Him

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One of the easiest things us men can to do pump up a look is to add a hat. Whether it is a baseball cap, a trucker hat, or a 1950s-inspired fedora, throwing on a hat can make any t-shirt and pair of jeans look like a really cool outfit. Celebs like Justin Timberlake, Johnny Depp, and Brad Pitt have been sporting hats for the paparazzi and the red carpet – making today’s man look effortlessly cool. You may not be walking a red carpet with your wife, but it’s time to look like you should be. Take a look at my picks for the best hats for men.

The best men hats keep you warm and add that special style to your look. We suggest wool men's hats, rugby men's hats and other hats from Gap, Ralph Lauren, Urban Outfitters and others.

Best Hats For Him by Preston Konrad

The Best You Can Get

  • D&G - Wool Drivers Cap

    Preston says: Throw your look back to the 1920s with this vintage inspired drivers cap. Vintage styles have really made a comeback in men’s fashion and this cap is a prime example of classic style with a modern twist. The cashmere lining is luxurious and comfortable and the signature herringbone pattern is perfect for a cool fall day. The back of the hat features a nickel plate Dolce & Gabbana logo, and the bill snaps down just like it should. Throw this on with a pair of classic ray bans and a leather jacket, and you may just be running from the paparazzi in SoHo.

    • Made in Italy
    • Cashmere lining
  • Gap - Bomber Hat

    Preston says: I think this is one of the coolest hats a guy can wear in cool weather. The classic lumberjack look is updated with solid navy instead of the typical plaid, and the shape is made less bulky for normal everyday wear. The earflaps hang down for super cold days and button up when the wind is not gusting too hard. Although the lining is not made of real fur but with polyester fleece, it makes for a breathable yet warming hat that doesn’t look like you’re about the cut lumber in the backwoods of North Dakota.

    • Hand wash
    • Fleece lining
  • Rugby by Ralph Lauren – Kicker Cap

    Preston says: Get your prep on with this awesome baseball style cap from Rugby. It features the Rugby kicker logo large on the front with the word rugby under it and fits like the one you wore growing up. The cotton has been washed and the brim is tattered and distressed making this cap look and feel just like the one you used to wear everyday in college. It is available in navy blue, white, and green and features a sharp leather closure and buckle on the back for size adjustment. Play on!

    • 100% cotton
    • Leather slider buckle in the back
  • Heritage 1981 - Herringbone Cap

    Preston says: This newsboy from Heritage is an incredible alternative to the Dolce & Gabbana version that will really help you get that look, for less. Coming in at a very low price, this cap is almost a no brainer. The brim is more curved for a funkier take on the classic, while the herringbone is surprisingly good quality for the price. If you think you might lose this baby one night out at the bar, you can totally buy two at a price like this.

    • 40% wool
    • 1.75” brim
  • Psycho Bunny - Skull Cap

    Preston says: I picked Psycho Bunny as one of my choices for best ties, and they’ve made the list again with this cool skullcap. The overall look is nothing innovative, but what makes this such a cool hat is the psycho bunny logo on the fold up brim on the hat...guys, it’s so funny. Forget the itchy version of this hat you used to wear when you were little, this version is made of 100% cashmere and breathes for supreme comfort.

    • Available in black and grey

You will be happy with any of these

  • American Eagle – Eagle Plaid Military Hat

    Preston says: The fit of this military inspired cap is ideal for almost any guy, with any shaped head. The overall look is not too deep like a beanie hat, but features a brim similar to your favorite baseball hat. The brown plaid is perfect for fall and the cool embroidery on the brim and face make it the perfect hat to give your plain white t-shirt a little rock star edge. The sale price makes this baby even more loveable.

    • 81% polyester
    • Machine wash
  • Urban Outfitters - Pinch Beanie

    Preston says: Bring out your inner Brooklyn resident with this ultra cool beanie from Urban Outfitters. The knit is chunky, making it look like great vintage find, and the back is pinched so it fits just right on your head. The hat is lined with ultra soft jersey cotton and can be thrown in the wash. This is a really cool hat… oh, and Johnny Depp called – and wants his beanie back.

    • Acrylic and cotton
    • Machine wash
  • J. Press - Wool Fedora

    Preston says: If you’re going to go classic, you’ve got to have the best of both worlds. The classic fedora is from the classic menswear shop J.Press. This fedora is the one every designer has been copying and selling in department stores for the last year or so. There are no crazy patterns, logos, or buttons on this version making it perfect for a night on the town or for a dressy event on a cold night.

    • Multiple colors available
    • 100% wool exterior
  • J.Crew - Wool Woodsman Cap

    Preston says: This old school style of cap has been pleasantly updated by J.Crew. The ribbed cotton in the back has not changed much from the original version, but the charcoal herringbone is classy and sharp on this old school style. A hint of prep lies in the use of traditional English wool and chino lining. I would say this is a must have for fall and winter.

    • Charcoal wool
    • Lined in cotton
  • Old Navy - Men’s Cable Knit Hat

    Preston says: Cable knit accessories never go out of style. This hat from Old Navy is a great, affordable way to look classy and stay warm at the same time. Available in multiple colors at a great price, this is one of those cold weather accessories that you should have a few of. Paired with a classic navy pea coat and skinny jeans… and you’re all set.

    • 85% cotton, 15% wool
    • Machine wash

Related Articles

With the best men hats, you'll look effortlessly cool. These wool men's hats and other styles will put you in the same league as Justin Timberlake, Johnny Depp and Brad Pitt who like to don men's hats. Always the best price, these rugby men's hats and other handsome hats are crafted by Ralph Lauren, Psycho Bunny, Urban outfitters, American Eagle and others.