My Ride To Work Essentials
I rode in to work today. Here are my essentials: Having a good tailbag makes riding around with stuff very easy. Mine is an old Cortech 24-litre expandable tailbag which is excellent. It fits my computer, purse, shoes and it's expandable so big enough for a weekend trip. You can find it for about $70 - $99 in-store or online here
Ride to Work Gear
I have a pair of Falco boots I picked up at @TownMoto http://eatsleepride.com/rider/1402 which are strangely comfortable, have a nice heel and are waterproof.
I added my day shoes, because as comfortable as motorcycle boots can be on the bike, you can't spend the day walking around in them.
Gloves are your ordinary leather work gloves from Marks I picked up for $10. They're great. I have about 3 pairs of 'women's motorcycle gloves' I purchased that fit like crap and feel horrible compared to these cheap and comfortable babies.
My Triumph Street Triple
Ride to Work shoes
Tail Pack
 Enjoy the ride!
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@jampy00 This tailbag actually comes with a rain cover. Which of course I don't need because it never rains when I ride. Only sunshine baby!
Funny you mention the glove issue, my wife has the same problem. Tried two pair both fit fine in store, use them for a few hours and she hates them. Only other thing I would say is pack your gear in a water proof bag first then into the tailbag, heck even a garbage bags will work in a pitch. Always be "over" prepared.