I wear my messenger bag high and tight and empty just like the cool kids I see in the videos, but the other cyclists in my city just laugh at my sense of style. What am I doing wrong?
Confused in Cleveland
Just like politics and good organic produce, cyclist style is local. Chrome is king in San Francisco, but Lycra still leads in much of the Midwest.
Ditch the steel SE Lager fixed gear bike, those ridiculously tight Swrve pants, hemp belt and your home sewn bag and replace it all with roadie gear. A good starter ensemble might include the Look 595, ridiculously tight Assos "kit", and Rudy Project eyeglasses. You can still wear your Sidi shoes, though you need to learn how to use clipless pedals. The roadies will still mock your piercings, PBR and smoking, but they'll let you ride with them -- probably in the "C" group -- if you can hang with the peloton.
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My one recommendation, seeing that you're in Cleveland and all, is to get the largest messenger bag you can find and carry it very low. That huge bag will make your, um, posterior look smaller by comparison, and if you're anywhere in the Midwest, that's probably a good idea.
Did I mention that I'm a Steelers fan? No? And that I almost got arrested in Cleveland once? Dunno how that slipped my mind.