Hats & Headwear: Our Favorites

Hats & Headwear: Our Favorites

The hat is one of the oldest piece of clothing on the human body.

Before the shirt, before the shoe, before any of it, there was a person standing in direct sun and deciding to put something between their head and the sky. Practical problem, practical solution, and then something happened along the way: the hat acquired meaning. Status, identity, trade, allegiance, era, personality. An entire civilization's worth of signaling compressed onto the six inches above your face.

We are still doing this. The dad hat pulled low on a boat says something different from the wide-brim straw on a Riviera terrace, which says something different from the worn felt cowboy in a Nashville bar, which says something different from the snapback at a summer barbecue. Hats tell people who you are before you open your mouth, which is either the most efficient form of communication available or a terrifying amount of responsibility for a piece of fabric and some stitching.

Here is the history, the summer guide, and the ten we think deserve a place in your summer hat collection.

A Brief History of the Hat

The earliest hat on record is worn by a man in a Bronze Age cave painting in the Lascaux caves, roughly 15,000 years old, who appears to be wearing a brimmed hat that would not look entirely out of place in a Western film. The ancient Egyptians wore the khepresh, the blue crown, and various styles of linen headdress. The Romans wore the pileus, a simple brimless felt cap, and the hat began its long career as a social signal: slaves were given the pileus upon being freed, which is why the pileus is still on the French seal as the liberty cap and where "throwing your hat in the ring" comes from, a signal of freedom and democratic participation.

The medieval period introduced the hat as profession marker: the merchant's flat cap, the nobleman's plumed affair, the peasant's simple coif. The sumptuary laws of Tudor England regulated what hats each class could wear, because the government correctly understood that hats were one of the fastest ways for the wrong sort of person to pretend to be the right sort. The wide-brimmed cavalier hat of the seventeenth century, with its extravagant plumes and theatrical tilt, is one of the great fashion statements of any era.

The nineteenth century industrialized hat production and democratized the result. The top hat, which emerged around 1800, became the definitive marker of the Victorian gentleman and was gradually replaced by the bowler, which John and William Bowler designed in 1849 for a gamekeeper named William Coke who needed something lower and sturdier than a top hat for riding under branches. The bowler eventually conquered every class from city banker to American West outlaw. Butch Cassidy wore one. Winston Churchill wore one. Charlie Chaplin made one his entire persona.

The twentieth century gave us the baseball cap, the trucker hat, the fedora, and the cowboy hat as cultural archetypes, each one carrying so much accumulated meaning that they function as shorthand for whole categories of American identity. The baseball cap originated in the 1860s Brooklyn Excelsiors and became the American everyman's hat by the 1950s. The trucker hat was created as a promotional item for agricultural supply companies in the 1960s and reinvented by Von Dutch and Paris Hilton in the early 2000s before arriving at its current position as the relaxed, ironic, infinitely wearable summer staple it has been ever since.

The cowboy hat has its own chapter.

The Cowboy Hat: An American Mythology

John Batterson Stetson designed the Boss of the Plains in 1865 during a camping trip in Colorado. He needed a hat that would keep rain off, keep sun off, and survive the conditions of the American frontier. He made one hat from animal fur he gathered in camp, wore it, found it worked, and mailed it to a manufacturer in Philadelphia as a prototype. The Boss of the Plains had a flat brim, a tall undented crown, and waterproofing from the felting process. It sold immediately and has not stopped selling since.

What Stetson designed, and what the Western has immortalized in every film from Stagecoach to True Grit to No Country for Old Men, is not really a hat. It is a proposition. The cowboy hat says something about the person wearing it: self-reliance, a relationship with the outdoors, a particular American romance with space and sky and the idea that the frontier, whatever form it takes now, is still worth riding toward.

Summer Hats Style

Summer is the season that makes hat-wearing mandatory. The sun is not subtle in July. Whether you are on a boat, at a beach club, at a summer wedding in the garden, or just walking between the car and the lunch reservation, the hat does work that sunscreen alone cannot do. And it does it while also being the single accessory with the most personality-to-dollar ratio in any wardrobe.

The dad hat is the versatile summer cap. Unstructured, soft, with a curved brim and an adjustable back, it works with everything from a summer dress to a linen shirt to a swimsuit cover-up. The key is the patch or the embroidery: it tells a small story. A good dad hat tells the right story about what kind of day you are having or what kind of person you are, and the best ones do it with a sense of humor.

The trucker hat is the dad hat's slightly more casual cousin: foam-fronted mesh-backed, slightly structured, built for the boat and the beach and the outdoor afternoon. The mesh breathes better than cotton in actual heat, which makes the trucker hat the most practical summer cap despite its casual connotations. It peaked aesthetically in the early 2000s, was declared over, and then came back because it was never actually over.

The cowboy hat is the summer statement piece. In felt for cooler evenings and mountain settings, in straw for beach and resort. The brim provides actual shade that a baseball cap cannot match. It requires a certain commitment to wear, and that commitment is what makes it interesting. Nobody is neutral about a cowboy hat.

The wide-brim sun hat is the European resort classic: the broad straw brim that covers shoulders as well as face, that collapses into a bag without losing its shape (ideally), and that photographs beautifully from approximately every angle. The French Riviera and the Italian coast have been producing great sun hat moments for a century, and the aesthetic is completely intact.

Top 10 Hats: Our San Martini Favorites

The full collection lives at San Martini's Hat Selection. Here are ten we would reach for first.

1. It's Martini Time Corduroy Dad Hat | $38 The corduroy texture sets this one apart from the standard cotton dad hat, giving it a slightly more tactile, considered feel. The message is the San Martini philosophy in three words. It works with a linen shirt on the boat and a cashmere crewneck in October. A hat that travels seasons and time.

2. Lane Cowboy Hat by GIGI PIP | $154 GIGI PIP is the American hatmaker that has become the gold standard for women's felt cowboy hats, made in Utah with a quality that justifies the price immediately when you put it on. The Lane is a clean, wide-brim felt with a cattleman crease that works everywhere from a summer festival to a dinner in Nashville. Buy it once, wear it for years.

3. No Crying On The Boat Foam Trucker Hat | $32 The best name in the collection and the most accurate hat for summer. The foam-front mesh-back construction is the correct choice for actual boat use, actual beach use, actual sun. The philosophy and rule is in the name. No crying. You are on a boat, have fun!

4. Shane Cowboy Hat by GIGI PIP | $162 The Shane is the most architectural of the GIGI PIP cowboy hats: a higher crown with a more dramatic brim curve that reads genuinely Western rather than fashion-Western. It comes in a range of colors from whiskey to merlot to chocolate, and the right color choice is the one that matches the leather in your life.

5. Oysters & Champagne Foam Trucker Hat | $32 The companion piece to the No Crying On The Boat. If the first hat is the rule of the day, this one is the reward for following it. Oysters and Champagne is the summer meal at the right hour, and this hat knows it.

6. Le Weekend Dad Hat | $38 "Le Weekend" is the entire vacation philosophy compressed into two words on a hat brim. It is also, practically speaking, an extremely wearable neutral dad hat with enough personality to be interesting and enough restraint to work with anything. The French phrasing is doing intentional work here.

7. Sun Hat Collection by KIN THE LABEL | $240 KIN THE LABEL's Sun Hat Collection is the premium wide-brim option for the Riviera and resort crowd: genuine sun protection, beautiful construction, and the kind of hat that photographs from a terrace above the Mediterranean and looks exactly right. The price reflects quality of materials and construction that will outlast a dozen fast-fashion alternatives.

8. June Rancher Cowboy Hat by GIGI PIP | $146 The rancher brim is slightly flatter and wider than the classic cowboy, which gives the June a more relaxed, contemporary silhouette. It reads festival, it reads resort, it reads a summer evening anywhere the dress code is suggested rather than enforced. The most wearable of the GIGI PIP lineup for women.

9. Cars & Cocktails Dad Hat | $38 Two of the best things that exist. This is the San Martini lifestyle in two words, and it is also an extremely good dad hat that will make you think of the very cars and cocktails you desire and admire.

10. Gigi Rodeo Trucker Hat by GIGI PIP | $48 GIGI PIP's trucker hat brings the brand's Western sensibility to the more casual format: a structured trucker with the quality feel and design detail that separates it from the generic foam front. The rodeo graphic makes it a statement piece rather than a background piece, and the price makes it the easiest entry point into the GIGI PIP world.

The One Rule

Every hat works better when you stop thinking about whether it works.

Buy the one that makes you laugh a little, or that has a brim wide enough to actually do something, or that is made well enough to carry the dents and the salt and the sunscreen of a whole season without falling apart. Wear it often enough that it knows your head.

That is the entire philosophy of hats. The rest is just history.

References

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