The other day I was wearing a pink Lacoste polo shooting a SIIG at the range.
I assume you mean Sig. I've carried a Sig in a fanny pack for years, but I understand that is considered either somewhat fey or at least out of fashion. Regardless, it holds a full-size 9mm and spare mag nicely.
Back on topic, I used a Brenthaven messenger bag when I was transitioning from a 17" PB in a backpack to a 15" MBP, and sometimes had to carry both. It wasn't bad at all, but I prefer a backpack from an ergonomic standpoint. I never worried about how the bag looked, but then again it was black cordura, not really very showy.
I kid. It's a bag! Humans have used bags for I don't know . . . probably a long time. They're to carry stuff. Not gender-related.
you don't have to wear the matching pumps if it makes you uncomfortable.
I rock a Louis Vuitton Petit Messager in the Terre color as a daily out bag (not for work) and love it, and so do all the ladies...look it up under E-shopping in the men's section, Men's Bags-->Messengers and Totes-->Damier Geant Canvas:
http://www.louisvuitton.com/us/flash/index.jsp?direct1=home_entry_us
Backpacks spread the weight over both shoulders if you have a lot to carry and you can slip them onto one shoulder if you haven't.
Manbags just make you look like a tryhard fashion victim and I don't see the practicality of having all that weight banging against your hip off a long strap as you walk. Some people believe in suffering for their art, however.
In short, just get whatever bag you want. I do what I want, so should you.
Sure why not. I have two messengers. Don't waste your time thinking what everyone else would think about you...