Bike: Expect a good beginner's model to start under $1,000, have 27 gears, and be crafted from light aluminum alloys; comfort-focused bikes have an upright pedaling position, flat handlebars, and broader saddles. For more performance (and more cash), expect lighter frames and drop handlebars. The Cannondale Sport Road 1000 (shown) runs about $1,900.
Shorts: You'll want Lycra, with a chunk of strategically stitched-in padding called a chamois (designed to be worn without underwear).
Jersey: Loud prints are de rigueur on club rides. True roadies only carry what fits inside the three small pockets―patch kit, pump, and energy bar. Descente Classic Half Zip Jersey, $65.
Helmet: Crash protection and, with good vents, natural air-conditioning for your head. Bell Ghisallo, $100.
Shades: Plastic (for safety) polarized lenses combat glare and protect eyes; photochromatic lenses lighten and darken. Specialized San Remo, $140.
Saddle: You want all-mesh, ultracush―worth a splurge. Saddleco Flow saddle, $130 (not shown).
Gloves: Gel padding lessens pinched blood flow in hands and softens road shocks. Pearl Izumi Gel Lite Glove, $36.
Pedals and shoes: Click-in style increases pedaling efficiency. Shimano PD-A515, $80. Compatible shoes from about $90.