There aren’t many times I’ve blamed Austin Butler for anything, but the renaissance of the henley might just be his doing. I’ve always had a semi-contentious relationship with the shirt. Somehow, it slipped into my closet and refuses to leave. A bit too casual, a bit too slouchy, it adds a boyishness to my appearance (my narrow shoulders and round cheeks don’t help) just when I’m trying to look like a Very Serious Adult.
The henleys I do own usually end up at the back of my closet, only making an appearance as a quick layering option or a shirt for painting the living room. But now, with its resurgence in menswear, I’m starting to see how wrong I’ve been. And while I still can’t forgive Butler for his unusual Elvis accent, I’m man enough to admit I want to look as good as he does in one.
The Henley’s Unspoken Rules
Like any adversary, it’s best to know its strengths and weaknesses. Unfortunately for the henley, it’s the same thing. The boyishness of the henley’s design—its slouchy silhouette, its collarlessness–are why people enjoy throwing one on for all-day comfort. The problem is, of course, that you don’t want to veer too far into the informality of the garment or you run the risk of looking like you’re still in your pajamas.
To combat this effectively, get the basics down with a henley and the rest will flow naturally. You should always go for a long-sleeve over a short-, you should always keep the collar open and never buttoned, and you should never try to be ironic and pair a henley with a suit or sports coat. Instead, a henley needs to stand on its own and, in a way, be defiant of the inherent structure of traditional menswear while still hitting the key points of quality, fit, and fabric.
Because the henley has an almost sophomoric look, getting the fit down helps in elevating this particular garment to being a legitimate staple in your wardrobe versus something you just threw on. The difference comes down to fit. While many henleys have a slightly looser fit, look for ones that have a slight tapering at the trunk to help slim your midsection and elongate your overall frame. If this isn’t an option, tucking into your jeans is perfectly fine. Most henleys have a bit of length to them that is perfect for this without too much bunching or extra fabric to worry about.
The waffleknit henley is often the default, but I tend to find this one a bit too close to thermal long johns. Cotton still reigns supreme here, but explore cottons woven with another fabric that can elevate the feel and look, including silk, wool, or even viscose. By understanding the margin of error for a henley is slim, it’s best to try a few and find the one that keeps you looking more like Paul Mescale and less like Nick from New Girl.
Top Henley Picks
Photos via UNTUCKit
UNTUCKit Stretch Cotton Herringbone Henley
With such a simple construction, it’s always surprising—and delightful—to find ways in which brands can put their stamp on a henley. UNTUCKit’s herringbone-designed fabric does just this. Made from a cotton blend, it’s breathable with a slight bit of stretch that’s great for all-day wear while the herringbone pattern adds a bit of texture to the garment that helps to elevate it just slightly enough to keep it interesting.
Photos via Huckberry
Flint and Tinder The Vintage Slub Long Sleeve Henley
This henley might be as classic as they come, but that is never a bad thing. Flint and Tinder’s slub henley has a slightly boxy silhouette that would work well for those with a slightly fuller frame, or equally for those with a broad chest for a great drape. Made from garment-dyed cotton, it’s a soft and simple choice for anyone who isn’t looking to reinvent the wheel, but invest in a simply well-made option.
Photos via Mack Weldon
Mack Weldon SILVER Long Sleeve Henley
Transitional weather means cool mornings and the occasional unseasonably warm afternoon. If by midday you’re finding yourself a little overheated, then Mack Weldon’s henley offers the perfect solution. Made from supima cotton woven with Ionic+ silver, this henley has anti-odor properties which helps to neutralize body odor and keeps you feeling (and smelling) fresh.
Photo via Merz b. Schwanen
Merz b. Schwanen Classic Fit Midweight Long Sleeve Henley
Perhaps the granddaddy of them all (or should I say Großvater?), Merz b. Schwanen’s henley hits the right balance between heritage, fit, and style for you to hit “add to cart.” Made on century-old loopwheelers, the German brand’s henleys have an almost artisanal quality to them, while being incredibly well-constructed. The extra-long packet and slightly draped shoulder both add to the vintage feel of this henley, which, paradoxically, is what makes it feel so modern.
