Hi all...hope everyone's been keeping well.

Every year Toronto's major media outlets hold a fun event to raise money for local charity and further the sense of friendly rivalry that characterizes our field. The different outlets assemble a rock or ska-esque group from among the staff, and a battle of the bands ensues. Like last year, I'll be on hand to cheer on the boys from our newsroom, and I'm now trying to figure out what to wear.

Actually, I think I have it mostly figured out. Since this event takes place in a casual bar setting, I figured this was a good time to break out my red jeans and handkerchief hem tunic that won such approval awhile back. I recently acquired a waxed denim moto jacket at insane discount with which I'm more than a little in love, and I do believe it'll be perfect with this outfit. What I'm struggling with is bags and footwear. Can I wear black booties with this outfit? I was hoping I could as a form of continuity with the jacket and pattern in the top, but I know it may be too jarring with the jeans. If I can wear my booties, is it better to tuck the jeans into them or leave them untucked? And secondly, should I carry the red bag that is similar in shade to my jeans and that can be worn across my body for the whole night, or should I take the snakeskin bag that's less matchy but slightly higher maintenance?

Pic 1 shows the jeans tucked in with the red bag, pic 2 shows them untucked, jacket open with snakeskin bag in tow. Please let me know what works. And if the black booties just aren't working for you on any level, say the word and I'll wear my pewter Cole Haan wedges. They're not as good in colder temps, but they'll do in a pinch.

Also, just for fun, pic 3 shows the outfit I wore to last year's battle of the bands. Similar idea, but I'm feeling better about my figure this time around.