I’m A NYC Bike Messenger, And This Is What I Wear To Work

One of the quickest ways to get around New York City is by bicycle, and no one knows that better than the city’s bike messengers. The job of zipping around city streets requires an ability to weather torrential downpours, snowstorms and vehicle traffic ― and bike messengers are pros at gearing up for the job.

We talked to two New York City bike messengers to find out how they keep warm, dry and safe. We can all take cues from their tips!

Kevin Bolger

Bolger wears colorful BMX pants from Fly Racing and a cycling jersey made by Primal Wear.

Kevin Bolger started as a bike messenger in New York City in September 1992 for Champion Courier. Over the years, he’s developed a colorful, high visibility style that’s both comfortable for him and practical for long days on the bike.

“I have colorful clothes,” Bolger said, laughing. “It makes me feel good. High visibility is a good thing in heavy weather.”

Today, he runs his own company, Cyclehawk, managing employees and orders via smartphone, and works part time with Manhattan Portage, maker of authentic NYC bags, messenger and otherwise. Bolger spends about six to eight hours a day on his bike, six days a week.

In cold weather, Bolger wears Continental Black Chilli wool socks. If the temperatures aren’t too cold, he uses cycling shoes with clips because of the power-transfer benefits that come from attaching foot to pedal. In cycling, shoes with clips that attach to a special pedal are called “clipless” (even though they do, in fact, have clips). His shoe of choice right now is the Fly Talon 2. If temperatures are freezing, or if it’s an especially wet day, he dons snow boots instead.

Bolger carries extra gloves and socks, as well as another top layer during the winter. “If I lose a glove or they get wet, it’s nice to have a backup. If my socks get wet, having an extra pair gives me something to look forward to,” he said.

For pants, Bolger likes the BMX version from Fly Racing because of the four-way stretch and durability of the fabric. They come with pre-shaped knees for added flexibility, suitable for long days on the bike.

He sports a cycling jersey with his company name Cyclehawk on it, designed by his buddy Chombo and produced by Primal Wear. Cycling jerseys have two or three pockets on the lower back for stowing snacks, phones, extra battery packs or whatever else will fit. Winter versions of cycling jerseys are often made with a fleece lining.

Left: Bolger's cycling jersey has several pockets on the lower back for stowing snacks, phones, extra battery packs or whatever else will fit. Right: Bolger locks into his bike with clipless shoes on dry days.

Left: Bolger’s cycling jersey has several pockets on the lower back for stowing snacks, phones, extra battery packs or whatever else will fit. Right: Bolger locks into his bike with clipless shoes on dry days.

“When it’s subzero I wear a Patagonia rain jacket and Arcteryx rain pants on top of my other layers,” Bolger said. “They stop the wind.” Garments that provide wind protection are essential when working outside. As most everyone knows, wind chill can lower the real feel of outdoor temperatures significantly. Bolger’s most valued piece in the winter is a good hooded windproof shell.

Some of this cold weather gear can add up to some big dollars, but Bolger said a resourceful person can put together good gear from a thrift shop or even the hardware store. His favorite gloves are insulated work gloves because they’re easy to take on and off. “And, if you lose one, the next pair is only a hardware store away,” he added. Plus, they only cost around $10 to $15.

“Everyone has their personal needs ― some have to have warm feet and some can ride with no gloves. Make sure to keep your core warm and eat healthy,” he said.

Bolger keeps his cellphone in a sandwich bag because it helps keep the charge longer on cold days. The thing to remember about the cold, he said, is that the next indoor stop is probably only 20 or so minutes away and will provide a chance to warm up. “Will and mindset are the best tools any bike messenger can have,” he added.

Bolger never tires of being a messenger. “I love riding my bike and I love New York City,” he said. “It’s a job that makes me feel alive.”

Even when he’s outside in wind and snow.


Some of Caro's favorite brands for cycling gear are Uniqlo and Supreme.

Some of Caro’s favorite brands for cycling gear are Uniqlo and Supreme.

Caro (who only goes by one name) has worked as a messenger for four years. She’s been in New York City for longer, but took a break from the messenger life for a while because of a guy, she said. “That was a mistake,” she added. “I started cycling because of freedom. I didn’t want to have to rely on any man to take me home.”

Caro moved to the Big Apple from near San Antonio specifically to be a bike messenger. “I’m from a place where the only light outside at night was the one from your front door,” she said.

Currently, she works for a private medical supply company delivering prescriptions and other supplies. She also manages an Instagram account, @malabrujanyc, created to help empower female, trans and gender-nonconforming individuals.

Caro buys a lot of her gear at Uniqlo. “It works well and is affordable,” she said. The stuff only lasts one season, but the price point ― a Heattech Turtleneck and a pair of Heattech Leggings go for around $20 each ― makes up for it.

Most days, Caro “rocks Nike Cortezes” – unless the weather is especially cold and snowy, when she switches to calf-high Hunter rain boots with Uniqlo wool socks.

Left: Caro's pants are made from a four-way stretch, water-resistant fabric. Right: Caro's neck gaiter/face mask is from All City Cycles.

Left: Caro’s pants are made from a four-way stretch, water-resistant fabric. Right: Caro’s neck gaiter/face mask is from All City Cycles.

Caro’s go-to pants are Chrome Industries Sylan 5-Pocket pants, because they’re made from a four-way stretch, water-resistant fabric. During the winter, she wears a pair of Heattech Leggings underneath for added warmth. If she’s out in steady rain, she breaks out her Showers Pass rain pants. Showers Pass makes cycling-specific clothing, so much of the company’s gear, including the rain pants, come with reflective trim for heightened visibility when biking in dark, rainy conditions. Jacket-wise, Caro loves her Showers Pass Atlas, made from fabric printed with reflective maps of cycling-friendly international cities, including New York, Barcelona and Paris.

“No gear keeps you completely dry forever,” Caro said. “If you’re out all day in a steady rain, you’ll eventually get wet. Uniqlo keeps you dry for about two hours, REI brand for a bit longer, and Showers Pass for about three and a half hours.” She carries an extra rain jacket with her on stormy days.

On her head, Caro wears the Giro Aether helmet. “I’ve heard lots of stories about people surviving crashes with this helmet,” she said. Her other favorite pieces of headgear include a Supreme 3M 5-panel hat and a neck gaiter/face mask from All-City.

Supreme, a well-known streetwear brand among skateboarders and bike messengers, underproduces most of its gear, which creates a thriving resale market and exclusivity. In other words, Supreme stuff is high on the street-cred scale.

Perhaps Caro’s favorite piece of gear, though, is the jewelry chain her friend made for her keys and wallet. She wears it, skater style, with the chain draped across her right hip, a pair of Sugoi fall gloves shoved into her back pocket, an extra-large messenger bag made by Mer Bags slung across her back.

Like a lot of her special gear, Caro measures high on the street-cred barometer.