I’ve been really into bolder shirts lately, which I think of as a spring equivalent of textured knitwear. Menswear writers often list your basic, plainly colored v-necks as wardrobe staples, but I find they only work well under suits and sport coats. On their own, they’re a bit too bland, a bit too business casual. So I prefer things that are more textured, such as spongey lambswools, twisted cables, or flecked Donegals. I find them more versatile. And infinitely better looking. They add visual interest to a simple sweater-and-jeans outfit and can be layered under casual outerwear.

It’s harder to wear textured knitwear this time of year, but the same idea applies to shirts. A bolder shirt pushes an outfit away from business casual territory; it adds visual interest. And while I still like crisp white linens and light-blue oxford-cloth button-downs – even on their own with tailored trousers or jeans – it helps to have some bolder prints for casual situations. They’re not as versatile as textured knitwear, but still useful when you want to make a spring outfit more stylish. The best ones I’ve found this season:

The Tom Selleck Look

Some of the easiest styles to wear are the plant-motifs commonly associated with Aloha shirts. It was the popularity of the brawny, mustachioed Tom Selleck in Magnum PI, after all, that convinced men that they could have the same magnetism if they just wore a hibiscus print. And while there have been a lot of bad Aloha shirts in the past – mostly campy themes at Tommy Bahama with green parrots drawn alongside sloshing martini glasses – many today can be worn in a more contemporary way. Think: with jeans and double riders, on their own with chinos, or layered under M-65 field jackets.

Notables in this category: President’s rangi shirt (available at Mr. Porter and Unionmade); Afield vibrant print literally named Selleck; Officine Generale subdued Dario; and Wings + Horns deck shirt. J. Crew also has a nice floral print in their diffusion Mercantile line. The shirt is a bit roughly sewn, but also only costs $32. If you can find it, they offered the same design last year in their mainline collection, which I remember to be better made.

Vintage-Inspired Workwear

The themes in this post aren’t clear cut, and often things in one category can be worn in other contexts. That said, many of the bolder prints I’ve been looking at have a 1950s-tinge to them. I’ve been searching for shirts I can wear with Japanese utility jackets and military-inspired outerwear. So naturally, many of the shirts have a mid-century feel, often drawing on vacation, Tiki, and workwear themes popular in the immediate post-war period. I think of these as better for slightly more vintage-styled outfits, rather than strictly contemporary styles.

In the first photo above, Bryceland’s Ethan Newton also shows how his store’s retro-print shirt can be worn on its own with raw denim jeans and white canvas sneakers. Swap the shirt out for a basic button-down and it would have a very different feeling.

Notables in this category: LVC 1940s-inspired Hawaiian shirt; Snow Peak camping shirt; Engineered Garments Afghan print; Chimala dotted print; Bryceland’s Groovin’ High; and August Fifteeth patchwork bandana shirt. Gitman Vintage, a brand that’s especially good for patterned button-ups, also has some elephant-themed batik prints this season (available at Need Supply and Superdenim). My barber sometimes wears a similar shirt he bought while visiting Vietnam, and he looks tremendous in it.

Contemporary Prints

For those who want something less retro, there are lots of contemporary prints that could be layered over boxy white tees and worn with slim-straight jeans. These are slightly more modern iterations of the mid-century classics, or things that draw from international traditions. Or they’re simply modern prints that aren’t necessarily about recreating a historical look.

I really like this blush pink shirt from Tony Shirtmakers, for example (sold at No Man Walks Alone, a sponsor on this site). Tony Shirtmakers is a Brooklyn-based textile printer and shirtmaker. Since the shirts are all handprinted using silkscreen methods, no two are the same. They would look great with jeans, a vintage tee, and some Vans. This is the summer outfit of guys who love picking their own fruit and telling you about their favorite Berlin-based, German-Norwegian pop-new-wave-synth indie band. But also get distracted by opportunities to talk about their time studying abroad in college.

I’m also digging this poppy print from Double Rainbouu, which reminds me of a Junya Watanabe shirt I regrettably missed out on last year. I think it would look great with black jeans and black leather jackets. This Officine Generale shirt could also be worn with casual suits and sport coats for a modern take on 1970s style (a bit retro, but today would feel Tom Ford-ish). And Lemaire has a great watercolor print that you could wear with loosely cut trousers. Just note it has slightly dropped, mid-length sleeves. S.K. Manor Hill has a striped shirt that can be worn the same way (that one is sold at Namu Shop, another sponsor on this site).

Notables in this category: Gitman Vintage batik shirt; Double Rainbouu Space Junk; Afield Selleck; Lurker orient shirt; Officine Generale Dario; Lemaire multicolor; S.K. Manor Hill striped shirt; and Tony Shirtmakers geometric print. Dashiel Brahmann can also be good for this sort of stuff, but given the small-batch nature of their production, stock changes often. This floral print, however, is supposed to drop soon.

Simply Unassailable

Some of the designs above can be a bit context specific – you may need a specific wardrobe in order to pull them off. For something unassailable, go for a dark colored pineapple print. The risk with boldly patterned shirts is that you can end up looking like a bookish nerd or party animal in a bad 1980s film. Simple themes in two-tone prints, on the other hand, are easy to wear.

Two Palms has a nice, navy rayon shirt with a pineapple pattern. I find it goes with almost anything, and it’s reasonably affordable at just $45. Granted, the construction could be better – the collar interlining isn’t the greatest and the interior is finished with overlock stitches, rather than something cleaner – but it hits on three good points. The construction is done in Hawaii, giving the shirt some authenticity; the fit is loose, but flattering; and the price doesn’t break the bank. Stay Ray also has a pineapple print shirt this season, and I think their design is slightly nicer, but it’s about double the price.

If you really don’t mind splurging, sometimes Valentino has good patterns. You have to sift through a lot of ugly junk (camo patterns and sleazy looking motifs). And the shirts are absurdly priced, often reaching upwards of $1,000. But sometimes you can dig them up for about a few hundred bucks on Yoox and eBay. This one, for example, would look great with grey wool trousers. A bit like this shirt on John Legend.

Lastly, this sailboat print from Gitman Vintage may just be the best one of the season. Wear it with contemporary outfits; layer it under workwear; pair it with jeans or chinos for a campout or BBQ. It’ll look better frayed and with ketchup stains. It’s modern, but slightly vintage-y. And it’s guaranteed to cost you an hour of your day, every day you wear it, because people will constantly stop you to say how much they love your shirt.