Now, thanks in part to the style cues set forth by people like Pharrell, Future and others, hats of all shapes and (sometimes absurd) sizes have resurfaced to reclaim their rightful place atop your head. Here, we examine a few of the most common styles, and give you tips on how to adorn your dome with hats that look good and are season appropriate.
Find The Right Type
Finding the right type of hat to wear really depends on two things: face type and climate. That’s it. Much like picking out sunglasses, knowing how your face is shaped helps determine the best headwear to rock. It’s also important to consider the hat both functional and stylish, but use some good judgement when wearing with dressier attire.
Panama - The Cadillac of straw hats, some variations of the Panama can contain up to 2500 weaves per square inch. Some places in the country don’t experience a true change in seasons until as late as October, so there’s still time to wear this with your favorite linen jacket and lightweight polo. But, unless the sun is out, this one stays in the closet.
Pork Pie - Made famous most recently by Breaking Bad’s character, Walter White, and his alter ego, Heisenberg, the pork pie hat is perfect for anyone trying to channel their favorite Guy Ritchie movie. Stout, with a circular indent, pork pies compliment those with oval-shaped faces and pronounced chins.
Boater - Think Andre 3000 when choosing to wear a boater. Unapologetically old school, boater hats are traditionally a summer formal hat, but can be worn in the fall with lighter, yet formal, attire like at a late-summer white tie event or your next barbershop quartet performance.
Newsboy - Considered the working man’s hat, the newsboy has been a staple atop the heads of American and European men since the turn of the 20th century. Sean Connery wore one in The Untouchables, so they have the bad-ass seal of approval. Newsboy caps tend to sit puffy on the head, so it helps to have a square, rugged face to offset the softness. Rugged tweed and wool versions are a nice alternative during colder months to keep that dome warm.
Driving Cap - The newsboy’s slimmer, sleeker cousin, driving caps are designed to fit tighter on the head, so make sure you get the fit right, or you’ll experience your fair share of headaches. Driving caps also sit lower on the forehead, so it works for guys with rounder faces and chins.
Beanie- A practice in no-frills practicality, beanies are the headwear workhorses. Get one in wool or cashmere to keep your melon super warm during the colder months. There’s no particular face type for this, because they conform to your head but it’s best to keep it to one simple, neutral color. You can try a pop of color as well but this isn’t the place for lots of patterns.
Baseball Cap - No explanation needed here, but it is time to consider losing all those fitteds you’ve collected over the years and graduate to something more subdued and mature. So like the beanie, keep it simple or go with low-key retro sports vibes. Definitely say no to leather though. 5-panels are definitely enjoying a moment too, and if you're going for more of a streetwear vibe, it's a move that's best pulled off with simple designs and colors.
Color Is Crucial
Regardless of which hat(s) you choose, make sure to stick with neutral colors and subdued patterns. Hats, for the most part, are considered statement pieces on their own. So there’s no need to jazz up an accessory that’s already going to stand out, regardless of what clothes you’re wearing. That means it’s probably a good idea to leave that Ed Hardy trucker hat at home.
Caring for a hat, regardless of how fancy it is, requires just a bit of forethought and a few cleaning products. For more formal hats, like Panama and boater hats, store them away in the box they came in after each use. Use a soft-bristle hat brush to dust away any loose dirt or dust that may accumulate and you should be good to go. Casual hats, like baseball, driving and newsboy caps, require much less fuss and, like your favorite pair of jeans, tend to look better with a little wear and tear. Treat beanies the same way you would a sweater, based on whatever fabric the hat’s made from.
A brief word on the do’s and don’ts of proper hat ownership: Don’t wear your hat indoors. Ever. We understand you’re excited to find a cap or formal hat that fits you perfectly, and refuse to spare any opportunity to show it off, but this is the perfect time to practice a little discretion. Men take their hats off indoors. Period. It’s one of the few acts of gentlemanly respect we have left in an arguably over-casual world. Do your part to preserve it.