Good topic. Looking forward to seeing what people post. Sorry I have no good advice! My main worry would be getting oil on my pant leg. I guess you have to roll it up or tie it with one of those tie things.
Chain guard! (says the guy who has been meaning to install one for 5+ years.)
I always roll up the pant leg. As for shoes, I leave a pair of shoes at the office. I normally ride with clipless shoes/pedals.
Heat of summer? I shower before I leave (only three mile commute from South Loop to Water Tower area), and wear different clothes. I change at work and give myself a pat down with Clorox wipes - after work, if I am going to ride 20 miles, I put on real biking clothes. If I am going straight home, I just change shoes, put helmet on, and roll up the pants. Then when I get home, I take the shoes off so I can moonwalk all over the condo.
My commute is between 13 and 15 miles depending on the route. I shower before I leave and have some clothing - suits, shoes belt, ties- at the office. I bring "software"- underclothing and a shirt in my pannier. I ride easy on the way in and clean up before suiting up. This works on most days. I generally wear bike clothing for the ride and then changed but on some days have worn a shirt such as a Club Ride jersey that will pass for office casual.
I'm similar to David. When I didn't have an office to store clothing and change, I'd bring khakis and a polo shirt, and change in a bathroom stall. It takes 10 seconds, and you can clean up a bit while you're in there.
If you need to ride in your work clothes, I really like these pants from Eddie Bauer; very comfortable, breathable, and they dry fast: http://www.eddiebauer.com/product/mens-horizon-guide-chino-pants/10...
Look for shirts with the same kind of fabrics (nylon, polyester, spandex) on their site. Search for the Travex series: http://www.eddiebauer.com/browse/travex/shirts/men/_/N-1z141d9Z277c...
No hot shower after a long, cold, maybe wet, bike ride in to work? No place to hang wet, stinkin' clothes? Not necessarily true!
There are lots of 'represented' union jobs down in the Loop...and most require locker rooms, showers and civilized amenities. Board room execs aren't the only ones with a private shower! Make friends with your building engineer and maintenance staff. If they don't have a locker room and shower they could show you, chances are they'll know of one nearby.
I used to roll out of bed and be on my way to work on my bike five minutes later. Try riding an hour early; avoid traffic, allow time to enjoy your ablutions, and get to your desk before your boss. You'll make points for that, and smell good for the office staff all day!
And usually a nicer group of guys you'll never meet upstairs...and very appreciative if you show up after work once or twice a month and buy rounds!
Im going to have to look into this.