lol..i usually match my outfit TO my bag. I would sit in front of my bag closet and say, "Which bag do I wear tonight"...then once I have it picked..I look at my closet to see what would look good with it! Then if I can't make up my mind,I'll call my bf and ask him which bag I should use...and go from there..crazy yup!
Well, I pretty much just go with the basics. If I have black in my outfit, I can go with my black Segur or a mono bag. If I have pink in my outfit, I can use my pink Trapeze or pink CB pochette. If I have light colours in my outfit, I'd go with vanilla Jasmin. Anything else, I just grab a mono or damier bag...I don't spend that much time matching or thinking about matching my bag to my outfit.