I think we all remember when I first got my hands on a legit, made-in-Hawaii, rayon (the only fabric it should be made of) aloha shirt. Even though these shirts by Two Palms were modern, the fabric, colors, and design/cut make it a great pass for a 1950’s-60’s aloha shirt. That makes it perfect for my wardrobe. I’ll admit that I haven’t worn them since that post, but as it starts to warm up for summer, they’re definitely going to take a few trips out of my closet.
Styling an aloha shirt is pretty easy. Because it usually features a bold print or color, you need to keep everything else neutral and solid. Wearing them with suits is okay but I think it looks just a bit “too much”; gives me a dapper-all-the-time feeling.
A sportcoat is a nudge in the right direction, but it still too much for me. I like how people did it in the 1940’s and 1950’s: tucked in with high rise trousers.
As you can see, applying the principles of “vintage casual” and tucking in the shirt (even though its short sleeve) looks pretty badass. It definitely helps if everything is tailored properly since aloha shirts are usually cut pretty large. While I like vintage looks (especially Blake’s true vintage ensemble), I think my frame is better served by utilizing more modern, slimmer trousers like Mr. Kenji Cheung of Brycelands & Co:
It is these modern, “vintage inspired” outfits that let me to create this post!
This has to be one of my favorite ensembles of all time. I followed my old sportcoat combo above and paired by red aloha shirt with the pleated trousers from my Vulture Suits DB. The high rise really help tie in the vintage theme even though these are much slimmer than what was the norm in the 1940-1950s. Pretty cool right? The ensemble is perfect for warm weather and a lot better than wearing jeans, not for the “formality factor” but the drape and lightness of the wool trousers.
You might even notice that the intensity of the shirt is different than the initial picture earlier in the article. That’s because I actually washed this shirt myself (don’t dry clean rayon) and during the soak, the colors faded a bit. I like how it looks now, since it’s a bit less bold and can be worn with more ensembles!
Red Aloha Shirt from Two Palms Hawaii, Brown trousers from Vulture Suits, Tassel Loafers (eBay)
To show you guys just how versatile this shirt is, I decided to wear the same shirt with an outfit even more casual than the previous one. It’s not sartorial (in fact, far from it), but the outfit is younger, sexier, and certainly more en vogue as rockstar chic. I didn’t like it untucked, so I kept it tucked into my jeans to echo the previous outfit and also give off some 90s vibes. Similar to Mr. Styles, I paired my aloha shirt with slim (not skinny) black jeans and some brown suede chelsea boots.
It’s slightly similar to the previous outfit, but the combo of the tailored shirt and slim jeans really does give a new dimension to the outfit. I like it because it’s a departure from the traditional cuffed jeans and sneakers that you could do if you wanted to incorporate denim.
I wore this on a slightly mild day, so I decided to bring along my trusty denim jacket. It’s not vintage, but this Gap one still holds up! I love the color and provides some more 80s/90s vibes to the outfit, but the fact that it’s not light wash makes it a more classic choice. As you can tell, I’d wear this if I was hanging out with my friends (which I did) or on a date! Maybe not the first date though.
Two Palms Aloha Shirt, Levis 501CT black jeans, Loake Chelsea boots (eBay), Gap Outlet Denim Jacket
Mixing The Two
Shoe choices dictate everything. A suit with sneakers instantly becomes casual while jeans and derbies dresses it up a bit. Here, Jeremiah keeps the same theme (aloha shirt tucked into jeans) but he swaps the boots for some suede penny loafers. With a simple shoe swap, Jeremiah turns his casual outfit into something slightly elevated! I especially love how the deep navy of the shoe ties into some of the colors in the shirt.
His shirt isn’t vintage or from Two Palms; it’s actually from Uniqlo! I love that they actually used the loop collar that you commonly see on vintage sport shirts. This collar (since it’s way different than normal ones) add an extra touch to the outfit and places it in a slightly vintage category. I don’t need the loop collar on all my casual shirts but I love having at least a few to mix my wardrobe up!
He’s wearing everything Uniqlo except the Banana Republic loafers
Aloha Shirts, whether you go vintage or modern, are a great way to keep casual this summer. They’re an classic garment that offers vintage vibes, color, and personality to your outfit without going overboard. The fact that most good ones have loop collars is also a great detail.
The best part is that they’re totally versatile! I obviously don’t live the sartorial life 24/7, so it’s great that I have something casual that can work with my tailored trousers and my slim black jeans. Having items that work for a variety of different styles (like the gab short jacket) is something that take pride in when adding pieces to my wardrobe!
How do you like to wear your aloha shirts? Do you like them with tailoring or rock star chic? Let me know what you think in the comments below.
Always a pleasure,
Street x Sprezza
Photography by Ethan W. and Scott E.