We got the history of American vacation wear out of the way in part 1, so now we can focus on the good stuff: what to look for and where to get it. First off, a lot of guys generally underestimate their ability to wear brighter, bolder, louder patterns. That’s understandable–a lot of men’s style is about standing out via details, cut, proportion, and texture, and about drawing attention to your best features, rather than OMG YOUR SHIRT HAS PALM TREES ON IT.
But if you spend most days in blue OCBDs and plain tshirts and haven’t tried on something bolder in awhile, give it a shot. Paired with more restrained complementary stuff, even just denim (not generally a vacationwear fabric), these types of shirts–as well as better-than-your-average polos, and accessories like caps, or even shorts–can be the point of distinction for otherwise classic outfits. Also, with a lot of contemporary designers revisiting the vacation wear theme recently, they stand nicely at the intersection of unimpeachable classics and current magazine-spread style.
Vacation wear never fell totally out of favor, so there’s plenty of reasonably priced vintage out there (more online than in thrift shops). I like Reyn Spooner’s reverse printed popovers, which are often sewn with the bolder print inside so you get a faded look on the outside (for example, bottom left above). Reyn Spooner also did/does a lot of button down collar popovers, which gives the shirts a little Ivy Look restraint. Many (but not all) of Reyn Spooner’s shirts are also made in Hawaii.
Most of these vacation shirts are cotton or cotton blends, but don’t be afraid of vintage rayon. Jesse has done a lot of pocket squares and scarves in rayon, a man-made, plant-based fabric, because “unlike silk, it doesn’t degrade over time, and like silk, it has an incredibly soft hand and takes vivid prints.” Vintage rayon shirts will be bolder than those reverse printed cottons. If you’re searching for vintage rayon shirts you’l also likely veer closer to clothes with rockabilly, rather than surf or tiki appeal–think “atomic” prints rather than hibiscus flowers. You’ll also see versions in barkcloth, a (usually) cotton weave that’s a little rougher in texture (but still soft), even slubby, and significantly thicker than, say, poplin.
The risks of vintage are (1) bad prints–and there are MANY, and (2) inconsistent sizing. Vacation wear shouldn’t necessarily be as fitted as your dress shirts, and I like my polo shirts pretty trim, but keep an eye on chest and sleeve measurements or you could be buying a
Modern Versions of Vintage Vacation Wear
The same people who make reproduction denim, like Toyo (Sugarcane, Buzz Rickson), also make excellent reproduction vacation wear. Toyo’s brands like Sun Surf and Duke Kahanamoku (named after Hawaiian swimming and surfing legend) are made to vintage standards but are cut somewhat slimmer, especially in the arms. For the truly bold, Star of Hollywood makes printed, high-quality rayon shirts that are definitely NOT beachwear. Also check out Yellow Rat for more hardcore vintage surf inspired wear.
I own several shirts from Engineered Garments that could be considered vacation wear–they’ve been doing big prints on summer shirts for years. I like this year’s subtler camp shirt with a paisley print (136GBP). These shirts will have a modern, more flattering fit than some vintage wear—I mostly wear mine with fatigue pants/shorts or jeans.
If you want pretty much the opposite of a vintage Reyn Spooner shirt, you probably want this Saint Laurent Paris version ($690). Before he left the label recently, Hedi Slimane was mining (milking?) California culture with takes on slip on Vans, trucker hats, and yes, leaf print shirts. A version I like more is Our Legacy’s colorful palm shirt (a rayon blend) (€200), which is slightly oversized and was styled with black pants or worn unbuttoned—you can really see the 1990s influence here. Not really my style but I dig that they’re doing something different.
More Than Just Shirts
I don’t recommend wearing more than one leaf print item at a time, but some of the same people who make solid vacation shirts make print and surf inspired shorts and printed knit shirts. My favorite source for vintage style swimwear is Birdwell. Yellow Rat does cool trunks, 50s style peg top pants, and nice bucket hats as well.