The Street Photographer's Guide to Hats

Baseball Cap — From its meager beginnings as an item of sporting equipment, the baseball cap has blossomed into the default headgear for dorky white dudes in cargo shorts everywhere, a category which includes most street photographers. This is an excellent hat for shooters seeking the sun protection of a front bill but who don't require the full shelter of a floppy sun hat, or who think they might look goofy in something with a full brim. The narrow aerodynamic design allows for quick acceleration when tailing pedestrian subjects on foot, and unidirectional brim allows the head and neck to rest easily against the furniture of public transit. The wide availability of baseball caps hats on the market —many with custom designs above the front bill— allow for expressive possibilities for photographers seeking to brand, promote, and advertise products or personal habits Leica.

Worn by: Yours Truly (shown), Matt Stuart, Matt Weber, Troy Holden, Ricky Powell

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Narrow-brim Fedora — The dapper fedora isn't just for hipsters anymore. Street photographers too have noticed its potential. The narrow cantilever provides sun/rain shelter while minimizing potentially negative wind effects. On the street fedoras can have a calming effect on subjects —especially in gentrifying or wealthy zones— lulling pedestrians into a shootable mood of complacency or wistful admiration. This is a good hat for film shooters or others with a nostalgic connection to the era of Hollywood film noir or Prohibition speakeasy, or for digital shooters using a camera with retro-styling. Memory cards can be tucked into the hat band for storage. This hat will look as good at the end of shooting season as it does at the start.

Worn by: Alex Coghe (shown), Rinzi Ruiz, Richard Bram, Jack Simon

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Floppy Sun Hat — A balanced blend of timeless traditionalism and cutting edge functionality, the floppy sun hat has been a favorite of street photographers for years. This is the hat that evenly lit the face of Vivian Maier in her many self portraits. The nanny savant pioneered the combination of floppy brim and waist-level viewfinder to create a sort of working-man's dark cloth to block stray sunlight from her ground glass. But that's not all; this hat's spacious underbelly shelters eye-level finders as well. The sun hat blends well on city streets as well as beaches, promenades, and other arid locales. The Hollywood styling and dramatically cantilevered brim imbue the wearer with a pioneering sense of adventure which expresses itself photographically in surprising ways. 

Worn by: Vivian Maier (shown), Helen Levitt

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Cowboy Hat — Street photographers do not wear cowboy hats. A proscription against such hats is written into the bylaws of street photography. This doesn't mean you can't wear one occasionally while practicing other sorts of shooting. A cowboy hat may actually be a benefit when shooting sunsets, waterfalls, and rodeos. But when hunting for decisive moments in shifting urban scenes, cowboy hats are strictly prohibited. Why? Just because. That's why. 

Worn by: Ansel Adams (shown)

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Space Shell — A protective shell is essential when shooting in hazardous environments like war zones, developing countries, outer space, or just a junket to the other side of the tracks. Although a construction hardhat might substitute in a pinch, for full 360 vision nothing beats the clear space shell. Weegee often used the space shell —with cutout mouth to release his cigar's exhaust— to photograph in lurid and combative situations. It's no accident that he escaped facial trauma for his entire career. The disadvantage of the space shell is that it may attract unwanted attention in certain "normal" environments, making fly-on-the-wall candid photography difficult. In most cases this is easily overcome by sheer force of personality. And even if the shell becomes an unwanted focus, it's a small price to pay for the security of head and eye protection. Because if you can't see, you can't shoot. Duh.

Worn by: Weegee (shown)

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Tweed Driver Cap — Picture yourself on a busy urban sidewalk surrounded by a mix of unwitting pedestrians, posters, buskers, and bums, all engaged in the daily dance. It's visual grist for your mill, just waiting for you to come along and deliver the clever juxta! Yes, you're about to climb into the shutterbug driver's seat and subjugate the masses to your aperture, and won't you look dandy doing so in your tweed driver cap. Crafted from world famous Harris Tweed cloth and handwoven by Scottish islanders, this cap puts a hop into any street photographer's step. With diamond quilted lining for comfort, leather trim, and trim anterior styling, the tweed driver cap fits easily into your camera bag when not in use, ready for action when you are. After the shoot is over and you're ready to relax, no worries. This hat blends equally well on the links! Just leave it on the head while you hit a few balls and recount the day's outing.

Worn by: Bill Cunningham (backward), Thomas Leuthard (shown), Yanidel

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Black Watchman's Cap — Ever since Randall McMurphy broke the wool ceiling in the mid-seventies, this cap has been climbing the headgear social ladder. At this point it's a well accepted accoutrement in gentrifying neighborhoods the world over. In rain or shine, hot or cold weather, indoors or out, a black wool cap allows the photographer to blend in while shooting hipsters, musicians, and proto-yuppies, or while ordering a latte machiatto. But that's not all. Want to shoot the homeless and destitute? Leave the hat on and blend in seamlessly. Either way, this hat's permanent stealth mode allows a level of candidness and discretion that photographers in other hats can only dream about. Truly a hat for all seasons and uses, with fully fashioned crown for custom shaping, and constructed of naturally hydrophobic material to minimize water effects.

Worn by: Daniel Arnold (shown), The Edge, Joe Aguirre, Jack Nicholson

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Leica Fur Pillbox Hat — Made of fur from sustainably harvested mink and stitched with biodegradable linen twine in Leica's Wetzlar factory, the classic black background with red trim accessorizes with a variety of Leica camera equipment. The large logo is clearly visible at wide distances, and puts your world on notice that you care enough to invest in the best. But as good as this hat looks, its design is backed up by world class functionality. The sleek circumference stays above the fray of camera knobs and dials while keeping your head comfortable at subzero temperatures. When used in warmer climates, just remove the hat to let cool air circulate. Of course luxury comes at a cost. At a list price of $1,800, this hat isn't for everyone. Most street photographers will probably be happy in an inferior headgear, and that's fine. Let them. But for street photographers with the means and discrimination to use only the best hat possible, Leica's fur pillbox hat is in a class of its own. 

Worn by: Top models (shown), celebrities, and the idle wealthy.

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Bucket Hat — The bucket hat has had an uneasy place in the fashion world since gaining prominence —and a certain degree of ridicule— in the 1960s TV series Gilligan's Island. Bob Denver's buffoonish character cratered the market for bucket hats almost singlehandedly, driving its wearers underground for decades, into comedy clubs, poetry slams, convenience stores, and other obscure locales. Photographers were no exception. But, in a bit of headgear jujitsu, the hat's meager stature has gradually enabled it to gain a foothold in recent years in the overlooked, under appreciated observer role. Worn in public, the bucket hat attracts little if any attention, allowing street photographers to pass through the world invisibly. In terms of functionality the canvas material performs adequately, sheaving rain away from the face and affording a base level of warmth. 

Worn by: Bruce Gilden (shown)

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Pink Pussy Hat — A latecomer on the street shooting scene, the pink pussy hat came out of nowhere to sweep the world by storm in January. When worn at rallies and protest, this hat allows street photographers to blend into crowds, and to express solidarity with surrounding rational (non-Trumpian) belief systems. The pussy hat comes in a bewildering variety of forms, colors, designs, and sources, stretching the platonic ideal of "pussy hat" into a globe spanning phenomenon. Most are hand-knit from wool for warmth and durability. If damaged, a home repair is often possible. The pink pussy hat may prove useful while shooting protestors, posters, and even the occasional feline candid, but if worn while shooting pussies, the photographer is likely to be belted in the schnoz. Destined to be a classic.

Worn proudly by: Millions around the world (sample shown)