Urban biking is good for you, fun, and in a lot of cities way more efficient than driving or taking public transportation. It doesn't really have any downsides—except for the bike gear that commuters typically use and wear. But it doesn't have to be like that. You can do better than neon vests and tight-rolled pants. Here are some places to start.
Looking good starts with your bike, and with a Big Shot, you can make that bike look exactly the way you want. The company has two frame options, a fixie/single-speed track frame, or an old-school cruiser, and you can customize to your heart's content. You can pick colors, details, and add-ons like racks. The bikes are simple, efficient, and ride really smoothly.
A lock doesn't just have to be a plain chain. Australian-made Knog locks, including the Bouncer U Lock, are as nicely designed as they are functional. The Bouncer, an 800-gram, hardened-steel U lock, is silicone-coated so it won't scratch your frame. Knog also makes small, bright lights (because you're going to need those, too).
Helmets are non-negotiable. There's no good reason not to wear one, even if you’re just riding down the block. Giro's Surface is sleek and simple, but still vented, so your head won't get sweaty, you'll look cool, and your dome will be protected if you get doored by a driver on his cell phone.
On a bike, backpacks are the way to go because they evenly spread out the weight that you're carrying. Ignore the guys on fixies with messenger bags, or you back will start hurting. Kletterwerks' 10-liter Market Bag rides close to your back, is quick and easy to get in to, and sits low, so you can look back over your shoulder when you're switching lanes.
Forget spandex, you dork. If you're biking around town you can just wear jeans, especially because Levi's makes bike-specific jeans. They're stretchy, water resistant, and have reflective tape on the inside seam, so you can roll your cuffs and be visible at night. They make other bike gear, including shirts and jackets that have similar properties, as well.
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