The Chicago bike commuter’s list

I bike to work every day I can.  Rain, snow, blistering heat, I try to let nothing stop me. At 3.1 miles each way, the ride is not long. But after riding almost 250 times a year for many years in Chicago’s four seasons (including two Polar Vorticies), those miles can feel pretty long.

I’ve acquired a lot of equipment over the years.  Here is a list of what works for me.


  • A bike helmet (or ski helmet), always
  • On temperate, dry days I wear my business casual clothes with reflective leg straps I bought at my local bike shop
  • I have multiple series of outerwear for cooler weather:
    • For 50-60 degree days, a lightweight, shockingly orange Reebok jacket with a built-in hood that I found on clearance for $11.
    • For 35-50 degree days, a fleece-lined running coat, light gloves, and either a light running hat or Smartwool liner hat
    • For 30-35 degree days, the same fleece-lined running coat with a thick fleece zip-up underneath, winter gloves, and thick hat
    • For 20-30 degree days, I migrate to true winter clothes. I wear a Marmot ski shell, thick fleece zip-up, winter gloves, and thick hat.
    • For 10-20 degree days, same as above but with a Smartwool liner hat, liner gloves, long underwear, and waterproof/windproof galoshes
    • For 0-10 degree days, same as above but with waterproof liner pants and possibly ski goggles
    • For -10-0 degree days, same as above, but with another layer of gloves, hat, sweater, and thick ski socks
    • For -20–10 degree days, same as above, but ride faster and pray…


I try to never carry a backpack. Instead, I use an Ortlieb Office Bag QL2 Pannier. It is waterproof, sleek, and has an amazing attachment system. I love it.


This is mainly for dry weather. I have slight adjustments for wet/windy weather, which I’ll post at a later time.