The Cyclist
The Outfit: Eschew loud and logo'd cycling gear and find a simple design like this Rapha jacket. Bib shorts (held up with suspenders) stay put for serious mileage, while cleated shoes by Pearl Izumi are sturdy but still breathable.

The Extras: Mount an iPhone-powered bike computer (called the Wahoo RFLKT) onto your handlebars to collect and display data.

Rapha rain jacket ($295) and lightweight bib shorts ($210). Pearl Izumi Elite RD III shoes ($200). Wahoo RFLKT iPhone-powered bike computer ($130).