chipcom.....
really good idea here, use the proper tools and only make it as complicated as need be.
There are a lot of variables (NYC in Aug is way different than san Jose in Aug

so what works for me may not work for every one but:
I have a five mile each way commute right now, and my special cycling gear is: gloves, clipless shoes, a helmet, and strap to wrap around my right pant leg.
I wear my work clothes, typically Polo shirt, Khaki pants (fridays jeans and the loudest hawaiian shirt I can sneak by the fashion police at home).
I carry my laptop, work shoes and often my sons backpack
I am out of shape and am only avergingn 12 - 14 mph...but with this short of a commute it really doesn't mak a big difference
For me 5 to 7 miles is about the max I would use this set up for, beyond that I would go cycle shorts and use my road bike.
My bikes is my utility commuter...... English 3 speed inspired. It is upgright and as simple as you can go without going igh (thumshifter 1/9 gearing) (When I use it for quick errands I don't bother with spd shoes or gloves )