Hawaiian shirts are totally ~cool for the summer~. They're light, colorful, and an easy way for any guy to incorporate fun prints into his wardrobe. To highlight their greatness, we asked 12 New York-based fashion gurus to show us how they style a Hawaiian. They prove Hawaiian shirts are so much more than your dad's vacation staple.
*Shirts seen below are models' own.
Blog: Jian Deleon
“Hawaiian shirts were first made with the excess fabric from women’s muumuus. In Hawaii the shirts are formalwear; people will wear them to work in place of a suit. They're the reason we have 'Casual Friday.' The shirts are about embracing patterns in general, and come in everything from postcard to automobile prints—or in this case, Star Wars.
The inspiration for my look was Leonardo DiCaprio in Romeo and Juliet. I'm imagining him on a Verona beach writing in his diary smoking a cigarette..."
Blog: The Metro Man
"With this outfit, I get 'Hawaiian chic' or 'cool dad vibes.' I like the general Hawaiian shirt trend. I feel like it's been happening for a couple of years now, but more guys have been wearing them and are more open to it. This one specifically I bought in a large. [Moti normally wears a small.] I like it oversized. It feels like you can wear them oversized with a grandpa style and it's chic."
Blog: Style Society Guy
"With this look I imagined being on a boat. The cargo shorts were for the extra pockets. I love how Hawaiian shirts have two pockets, because I tend to throw my sunglasses in them. I also like how lightweight and thin the shirts are. It's easy to put a tank top on under and get away with rolling up the sleeves of the Hawaiian shirt if you want. The scarf was an add-on because I think it jazzes up an outfit — it adds a little New York City 'cool' to the look."
Blog: Real Guys Wear Ties
"Every year I kind of pick my favorite trends for whatever season we're going into, and for summer I'm obsessed with prints in general. This year I started seeing Hawaiian prints infiltrate themselves outside of the 'dad vacation shirt,' and now I've put my mark on it.
In general, I'm all about mixing prints, but I don't like to do it obnoxiously — instead I opt to do it subtly. That's why I had the print on my shoes so it's not all in your face."
"I get inspiration from mixing masculine and feminine. I have a beard and I'm a burly dude, so de-masculinizing myself for this look was important.
The Hawaiian shirt trend for me is fun because they have a traditional connotation but allow me to incorporate color into my wardrobe. It's less about the print and more about the color. This one has bolder brights and blacks that really break it up and make it wearable. When I styled my outfit, I played up the color and kept it bold and basic.
This is something I would wear on a regular day. I didn’t want to style something that seems unattainable for fashion. I’m of the mind that things you remain wearable, achievable, and likable."
Blog: Scout Sixteen
"I would say my look is more of an urban-jungle tropical vibe. I spend a lot of time in the city, even though I travel a lot. [New York City] will always be my inspiration. The trend of Hawaiian shirts is funny to me because when I was growing up, my dad would wear Hawaiian shirts from Eddie Bauer and Tommy Bahama, and seeing them resurface in a chicer way is really nice."
Blog: Denny Balmaceda
"Pairing basic modern staples with unique quality vintage is at the heart of my personal style. With this outfit, I built the style around a colorful vintage Hawaiian shirt for its lightweight practicality. I also embraced worn-in jeans and eclectic accessories to complete the look. While I love experimenting with an array of styles, I find that creating a uniform consisting of key articles removes the guesswork in getting dressed while providing the freedom to show personality through texture and color.
I'm a cinephile and much of my style inspiration comes from films. In movies like Romeo+Juliet and Scarface, iconic characters are costumed in Hawaiian shirts to illustrate a particular kind of masculinity. These men are tough and virile but also unafraid to dress flamboyantly and show a bit of flare. I see the Hawaiian shirt as a piece that represents my carefree approach to life, and also my strong point of view."
Blog: Fashion Goggled
"I'm a huge vintage connoisseur, so Hawaiian shirts have always been in my wardrobe. I'm happy they're back for sure. With this look, I liked dressing the shirt up a bit with a white jean and boot versus a short short. I love how deep the color of this shirt is; I like switching up my normal style for this rich color versus a pastel. I'm definitely giving laid-back vibes."
"For me, I love that Hawaiian shirts used to be that thing that your dad would wear on vacation that would embarrass you, but now younger guys are getting into cooler patterns and bolder prints. I think they're a fun summertime trend that’ll definitely be around all summer.
My inspiration behind my look today was to pare down the 'crazy' prints with white jeans and white sneakers, making it fun to just go around the city in."
Blog: One Dapper Street
For this look, I wanted to take the Hawaiian shirt in a different direction. While the fabric of this particular shirt is loose like a traditional Hawaiian shirt, it's still more fitted and not super long and doesn't have wide sleeves. Also, this is a good cut of shirt, it's significantly more fitted. I felt like I took the shirt and made it more New York City.
For the rest of the outfit I classed it up and went with slacks and a clean sneaker. To me, this is as close as you can get to wearing a Hawaiian shirt in an office [in a city like New York]. I paired all of that with very subdued, simple accessories — nothing overly crazy. And for the sunglasses, the lenses tie the blue of pants back in and add a little summer flair."
Blog: Oh Anthonio
"I think Hawaiian shirts are great. They’re not just for your dad. The look I went for was cool, skater, hip-hop vibes. I tried to keep it casual and imagined myself as a kid. I love Hawaiian shirts and I paired this one with some overalls, because what's more laid-back than that?"
"This outfit is my personal take on a Hawaiian shirt. I got it in Copenhagen and it's technically a blouse. The material is lightweight — it's a linen cotton blend, basket weave. I like that it looks like it could be 100% linen but isn't. The shape of the shirt is more androgynous. I like how Hawaiian shirts are more relaxed and about letting loose because I feel like a lot of men's fashion is pretty buttoned up. I like that these shirts kind of break that notion down.
My inspiration for this outfit was 'grandfather vibes.'"