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BMC's Alpenchallenge AC01 comes with a SRAM X1 drivetrian, and that's a big deal. You only get one front chainring, but you get a gearing ratio similar to bikes with multiple front chainrings with fewer moving parts to maintain. A short chainstay makes it super-nimble, and you can fit it with fenders to keep the spray off your back. $3,700 Jakob Schiller
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I won't ride in cool or cold weather without one of these base layers. Period. A base layer is crucial for wicking moisture and keeping you dry. That way, if you work up a sweat while pedaling, you don't shiver at the next stoplight. There are a million base layers to choose from, but Bontrager nails it with a nice blend of synthetic materials and wool. $70 Jakob Schiller
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The Boreas Echo pack is waterproof. And by waterproof, I mean you can haul it through a drenching rain and not worry about your laptop, because it'll be fine. No fussy rain fly here—the Echo is just an ultra-light dry bag made for bike commuters. Other nice features include a draining pocket to hold your wet jacket after the ride and a reflective print to keep cars off your ass. $140 Jakob Schiller
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Candence's jeans are made from raw 12-ounce denim with a reinforced seat section, making them just the thing for riding in all kinds of conditions. Beat 'em up as much as you want; they'll take it. They also look great, and with the tapered fit, you can wear them over a pa base layer. Be warned: they take some time to break in, but once they do, they feel custom made. $110 Jakob Schiller
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The days are still short enough that I wind up riding in the dark all too often. I've been using Light & Motion's Taz 1500, which puts out a blinding 1500 lumens at full power (that rivals some car headlights). Thanks to a sealed design, it works in snow and heavy rain, and the battery doesn't crap out when the mercury drops. $300 Jakob Schiller
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Unlike most all-weather cycling jackets, which use nylon or other synthetic materials, the Geraldine City Jacket is made from cotton waterproofed with a polyurethane treatment. The cotton has an understated look that doesn't scream "bike geek," and the piece is stylish enough to wear in business settings. A cyclist-friendly longer cut in the back and well-placed pockets make it perfectly suited for pedaling. About $270 Jakob Schiller
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Cruise a few miles in cold weather and your feet are goners without the right shoes. These Giro Alpineduros will keep your tootsies happy. There's a healthy helping of PrimaLoft insulation built in, and a waterproof liner keeps you dry while you bomb through puddles. Ride them with SPD pedals, or on flats with the cleat cover. $200 Jakob Schiller
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You'd never guess these Italian-made, high-quality leather boots were made for cycling. But things like a toe cap designed for caged pedals and small reflective details make the Pedaled Mido perfect for piloting your whip. Choose one of four colors, including a bold green with red shoe laces, for a fashion-forward look. $280 Jakob Schiller
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If you don't have insulated boots, you need shoe covers. Yes, they look dorky as hell, but they work. Castelli's Diluvio shoe covers fit several types of shoes, plus they're cut high to protect your ankles and shins under your rolled up pant leg. Reflective sections glow at night. $65 Jakob Schiller
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Get yourself a Indisce Blazer by Arc'teryx and it'll almost certainly be the fanciest bike jacket you'll ever own—and the most expensive too, at a whopping $650. But the Indisce is as finely tailored—and sharp---as other high-end blazers. Also, it's made with Windstopper 3-layer fabric, so while it won't keep you dry in a downpour, it'll block the chill on blustery days. Jakob Schiller
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Mission Workshop's Sansom isn't as waterproof as a traditional rain jacket, but with NanoSphere coating on its Turkish stretch cotton, it'll keep you dry in a March drizzle or an April shower. The coating also keeps other liquids like, say, an IPA from ruining the shirt, and your day. Plus, it looks great under a blazer with a pair of jeans. $195
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The Salsa Warbird is made for gravel grinding, a niche in which people race hundreds of miles on gravel roads. With a lower bottom bracket, clearance for fatter tires, and a carbon fork, it eats chop and makes for an ultra-stable ride. For these reasons, I've come to love it as a bad-weather commuter. The disc brakes are great addition. Choose between titanium, a full carbon frame, and two aluminum versions. $2,000-$3,500 Jakob Schiller
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The Frazier glasses from Spy are not made specifically for cycling, but they're suited to it. The frame and lens design keeps wind out of your eyes even at high speeds. They're also built from Grilamid, the same material you'll find in the shell of many ski boots, so they won't shatter if they fly off your face. $155 Jakob Schiller
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Need to keep your dome warm? There are bike beanies and buffs, but nothing matches style with function as well as the Urban Sprinter cap from This is Cambridge. These things are hand made with British wool and imported from across the pond, so it can take a couple weeks before one lands on your door. But it'll be worth the wait. About $41 Jakob Schiller
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