Accessorize With Style: Pairing Hats With Men’s Outfits

Man looking into a circle mirror wearing a tan felt men’s casual hat with jeans and a linen button-up shirt

Somewhere between your voice dropping an octave and the first crush you thought was “the one” ghosting you, you hopefully found your style—and now that includes hat outfits. Maybe you already have a closet full of men’s dress hats and men’s casual hats, but you need some inspo from a trusted men’s style guide. 

That’s us. 

Two Roads isn’t going to sit here and pretend that styling outfits with hats will wildly change your life and solve all your past or future relationship problems. But we sure as hell can promise to put a good-looking, high-quality hat on your head while you stylishly stumble through this messy thing called life.


How Can a Guy Look Better in a Hat?

Distinguished man turned around looking to the side wearing a patterned blue suit and brown straw men’s dress hat

Hats can make any guy look better through good sizing, outfit coordination, and hat maintenance. For the modern man who wants to look better and feel better in a good hat, here are our three top ways guys can achieve this:

  1. Find the right fit. Men’s hats that fit too loosely look sloppy. Men’s dress hats that fit too tight lead to awkward stares and potential headaches. Just because you buy your hoodies in size “L” doesn’t mean your head measurement is an L too. Learn how to get a perfectly fitted hat here

    To help you feel confident with your hat size, we offer the Two Roads Damnson Guarantee. If your hat doesn't make you say "Damn, Son!" when you look in the mirror, we'll cover your shipping to send it in and find the right fit for you.
  2. Proper hat care. Girls have skincare. Men have hat care. Taking care of your hat so it looks good will make you look more attractive. That may seem obvious, but you’d be surprised how many sweaty and smelly hats we still see in public. Pro tip: People generally love a hygienic man. Hat care is more than throwing it in the dishwasher or washing machine. Two Roads goes over the best ways to take care of your hat.
  3. Coordinate with your outfit. Are hat outfits right for every guy? Absolutely. Do all hats go with every look? Absolutely not. Styling and accessorizing your hat is an art form Scroll on for our favorite ways to put together hat outfits. 

    One quality felt fedora hat can be as casual or formal as you’d like based on accessories. Pair it with a navy suit, and you’re ready for date night or a summer wedding. Dress it down in sneakers, and you’re prepped to level up even the most menial errands, chores and meetups. 


How Do Men Match Hats With Outfits?

Man on the sidewalk of an empty street wearing a navy suit jacket, button-up shirt, blue jeans, and a navy men’s dress hat

Two Roads men match hats with outfits through color coordination, mixing patterns and textures, and showing off their personalities.  

  1. Color-coordinate hats with matching colors. Try neutrals that match anything. Throw in other accessories like watches, bracelets, and rings to complete the look.
    Man covering his face sitting outside of a shop wearing a pink patterned zipper shirt, pink men’s hat, watch, bracelets, and rings.
  2. Experiment with solids and patterns to give more texture, depth, and life to your outfit.
    Man outside grabbing the bottom of his patterned knitted sweater in a felt fedora men’s casual hat
  3. Show off your personality with subtle or not-so-subtle hats, bold colors, or fun accessories like necklaces and sunglasses. 
    Man leaned up against a concrete wall wearing a pinstriped button-down shirt, necklace, sunglasses, and a white straw hat


How Do You Style a Hat With Jeans?

Man sitting on a stool over a patterned rug wearing a denim jacket, black denim jeans, Chelsea boots, and a felt fedora hat

Hats are styled best with jeans when you take into account the occasion. Where are we going? Anniversary date? Choose the classic rancher. Country concert with the boys? Stand out from all the ultrabasic boy cowboy hats and opt for a straw sun hat instead. 

A single black felt hat or a neutral palm straw hat can give you so many drastically different vibes. Pair it with a white Costco V-neck versus a patterned Nordstrom button-up and jeans, and you have two entirely different men. Both are outfits we love. There’s just a time and a place for them. 


Shop  Men’s Dress Hats &  Men’s Casual Hats at  Two Roads

Have you ever seen Met Gala or Oscars recaps on Instagram and thought, “What the hell are they wearing?” I promise someone has probably thought that about you too. And that’s okay. That’s the beauty of styling men’s hat outfits. Your outfit and your style are just that—yours. So, who cares what anyone else thinks? 

Follow our guide or don’t. Two Roads fully supports you blazing your own trail! Just look your best in your hats doing it. 

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Four Two Roads men's hats for smaller heads stacked atop one another in white, brown, green, and black

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