Should I buy a brown leather satchel? What should I pair it with?

It goes with anything! Shorts, skirts, dresses, even maxi apparels. Which is why, yes, do buy it if you can find a good one. It is SO versatile and it allows your clothes to stand out if that's what you are going for. Be more careful when it comes to colour clash. I wouldn't carry it if my top/dress is brown. White would match it perfectly, but any other colour is fine. Remember to look for a pair of closed-toe footwear to match your satchel! Loafers, pumps, oxford shoes would be great :D

http://store.americanapparel.net/amanda.html?cid=195
(In Tan Leather)

http://www.asos.com/Asos/Asos-Mexico-Leather-Interwoven-Shoe/Prod/pgeproduct.aspx?iid=971198&cid=4172&Rf-200=10,14,26,13&sh=0&pge=0&pgesize=20&sort=-1&clr=Tan

http://www.asos.com/Asos/Asos-Frenchie-Knotted-Low-Wedge/Prod/pgeproduct.aspx?iid=918889&cid=4172&Rf-200=10,14,26,13&sh=0&pge=0&pgesize=20&sort=-1&clr=Tan
(You probably can pull this off if you don't have big feet)

http://www.asos.com/Asos/Asos-Mikey-Leather-Woven-Lace-Up-Shoe/Prod/pgeproduct.aspx?iid=935355&cid=4172&Rf-200=10,14,26,13&sh=0&pge=0&pgesize=20&sort=-1&clr=Brown

http://www.asos.com/Asos/Asos-Hampson-Crossover-Lace-Wedge-Shoes/Prod/pgeproduct.aspx?iid=963761&cid=4172&Rf-200=10,14,26,13&sh=0&pge=1&pgesize=20&sort=-1&clr=Tan

http://www.asos.com/Asos/Asos-Priya-Leather-Gladiator-Slingback-Shoes/Prod/pgeproduct.aspx?iid=878252&cid=4172&Rf-200=10,14,26,13&sh=0&pge=1&pgesize=20&sort=-1&clr=Tan

http://www.asos.com/Asos/Asos-Morse-Leather-Fringe-Tassel-Loafers/Prod/pgeproduct.aspx?iid=1147808&cid=4172&Rf-200=10,14,26,13&sh=0&pge=2&pgesize=20&sort=-1&clr=Tan

Two-toned shoes like might not be so compatible so steer clear of them(:

Ask/Tell me anything (: