I never thought I’d be saying this, but I’m a fan of Hawaiian shirts. If you would’ve asked me if I would be willing to wear one out in public a year ago, I’d probably laugh in your face with a big “HA!” While the trend often gets a rep for being a “dad trend”, my father was actually never the type to wear tropical-print shirts. Nine times out of 10, you could find him in his favorite worn-in polo shirt with shorts. ICYMI: the trend has clearly been making its way back into our hearts, thanks to Stranger Things‘s Jim Hopper who had a pretty amazing Hawaiian shirt collection during the show’s third season. My earliest memory of the trend is actually Leonardo DiCaprio’s technicolor Hawaiian shirt in Baz Luhrmann’s 1996 film Romeo + Juliet, and it’s forever ingrained in my mind.
During my search for the perfect Hawaiian shirt, I came across one from Urban Outfitters that looked almost identical to the one Leo wore in the film. If that wasn’t a sign to give it a try, I don’t know what is. If you’re wondering how to pull the look off without looking too cliché, I’ve got you covered. Ahead you can find two simple ways of giving the Hawaiian shirt trend a try if you’re a newbie like myself. From tucking the side of the shirt into high-waisted jeans to tying it in a knot in the front and wearing it over a slip dress, I found myself feeling pretty comfortable in these wild shirts. Sure, the print on the Leo-inspired shirt was a little bold for my taste, but styling it with key pieces that I wear on the daily made the trend feel a lot more wearable. I even shocked myself and wore it again with shorts and Birkenstocks the following weekend. Keep reading to see the looks and shop some of my favorite selections, ranging from a rad UO shirt that rings in at $69 to an ultra-luxe take on the trend from Prada.