Bag color

In a perfect world, I would have a bag color for each shoe color I own.

That being said, black and dark brown are always safe options. Chose whatever you like more.

Neutrals are never a bad way to go: black, brown, tan, dark gray, even oxblood or British racing green.

I have a dark green/forest green bag that goes well with any outfit. Love it

Depends on what color sleds / oxfords you normally wear. I wear alot of british tan so I got a british tan messenger bag

The most versatile and official color is black. But if you have lighter shoes prevailing - it may be worth choosing the lighter color of your bag

I have an oxblood bag, it looks nice and is unique compared to brown and black ones you'll see everywhere. Fairly versatile, goes with lots of colors

Black/Dark Brown, that way all your shoes match (unless you're the new person that I just hired who owns dark blue dress shoes).

Nobody will care either way but dark brown.

Surprised no one has mentioned navy. I think the silhouette and build of the bag is more important. I have both of these Filson bags in navy:

http://fil.sn/0wXxT

http://fil.sn/8qg24

I have a pigskin (heavy grain medium/light brown) bag that was a gift from Wilson to an AFL team. It sticks out like a sore thumb, but makes an awesome conversation starter. When not visiting clients, I use a basic black laptop case.