Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.
To me, there isn’t a style of shirt (without a collar, that is), that’s more versatile or rugged than a great short-sleeve henley. Although expressions of style and masculinity are changing all the time, there’s no doubt that a stylish henley is a still a reliable go-to if you want to upgrade your game and look a little tougher and stronger — or simply better in general — and that’s certainly true for the below tips on how to style a henley for summer. That goes for long-sleeve henleys with a vintage look, and it goes for fashionable short-sleeve henleys fit for fighting the warm weather. The button placket on well-made henleys adds some nice visual interest to looks both casual and a bit crisper, and in the right fit and color (like the slim-fitting indigo henley) below, you can wear the piece on its own with slim chino shorts or layered up under an unconstructed blazer for unique high-low style that can go to the office on a casual day and out on a date thereafter (I bet you’ll look better than the fella in the ill-fitting suit — trust me). It can be a bit of a process to switch from a plain white tee to a knit with more texture, color and visual details (even if it is just a simple button placket). But those added small details make it a worthy style upgrade — especially when you ditch the long sleeves in favor of a piece that’s just as trim-fitting, yet a heck of a lot more ready for the warm weather. Invest in one that’s well-crafted and you can rock it under a spring jacket, beneath a fall blazer or as a complement to a warm shawl cardigan in winter. For now though, focus on great chinos, solid suede boots and other accessories just begging to be worn on a warm summer’s day. Chime in on the #OOTD discussion at our very own Style Guide Facebook page, and we’ll see you out shopping.
Pair a short-sleeve henley with staples you might already have in your closet, like stone chinos and suede chukka boots.
The Henley: Jason Scott Banks Short-Sleeve Henley in Indigo — $96: Nearly $100 is a certainly a steep price to pay, but that price gets you exceptional quality, terrific Peruvian fabric and finishing touches like antique metal buttons on the placket.
The Chinos: Taylor Stitch Slim Chinos in Light Stone — $98: Taylor Stitch chinos have been a Style Guide favorite for some time now, and the reliably ideal fit and excellent fabric quality and color make these a fine match for that indigo henley.
The Boots: Thursday Boots Honey Suede Scout Boot — $149: Just as with those Taylor Stitch chinos, the Scout Boot from Team Thursday has received positive reviews in this neck of the woods, for comfort and quality as much as looks. This rich Honey Suede pair really does have it all.
The Socks: American Trench Edo Collection Socks — $19.50: Nearly $20 for a pair of socks? You’re darn right, and they’re some of the best (if not the best) ones you can rock that are made in America at family mills. Plus, the color pops just the right amount against the faded indigo henley.
The Belt: J. Crew Factory Double-Striped Webbing Belt — $14.50: Again, it’s a little counterintuitive that a belt would cost less than socks, but this piece is a bargain number that can be styled into several looks (see my Instagram for more examples, will ya?)
The Sunglasses: J. Crew Jack Sunglasses in Silver Navy — $98: As first seen on this site’s roundup of the best men’s sunglasses for summer, this pair of aviators is simple yet sleek and stylish (not to mention pretty cost-effective).
The Trunks: Tommy John Second Skin Titanium Trunk — $32: More than $30 sure is a heck of a lot to pay for underwear, but with what Tommy John can deliver in terms of quality, it’s worth it. The Dark Titanium color shown here has sold fast, but check out their other colorways here.
The Watch: Timex x Red Wing Waterbury Chronograph — $158: Timex and Red Wing really have thrown everything they’ve got at this standout watch, with a strap crafted from rugged Red Wing boot leather and a sturdy, classic-looking dial that’s super-functional and ready for just about anything (including NYC style adventures).
Sure, chinos and a henley might seem like a simple outfit combination at first glance, but it’s the upgraded, slimmer fits, richer colors and better quality that make this look acceptable for everything from grabbing beers at the bar to leaving early on a casual Friday (perhaps with a light grey blazer, if I do say so myself). And the other pieces in this ensemble, from a warm-weather friendly cotton belt to suede chukkas, can work in multiple seasons. Finally, there’s truly no bad time for a durable leather watch or a subtle-yet-stylish socks or crisp sunglasses. Making these pieces work in your favor by adding a lightweight sweater or swapping in a stainless steel dive watch is definitely going to pay style dvidends. Do we read each other loud and clear? Yes? Excellent.
‘Til next time!