I've always been a small bag gal. I'm pretty averaged sized. 5'6", 130 lbs. Here's the style of Coach purses I have and use: Legacy Leather Flap (10324) (my current fave, it's in whiskey) Soho Small Flap (in sig and black leather) A few swing packs Hamptons weekend spring 2006 patchwork tote (small) Dot Demi I also have the Legacy Leather Shoulder Bag in pond (10328) but it's just sitting in my closet in it's dust bag. I've NEVER used it. I feel it's too big for me but I know it's because I'm not used to it. I don't carry a ton of things but I will say, my Legacy Leather Flap is FULL and things have to be put in just so or they won't fit. I really want to carry a bigger bag! LOL, you're probably thinking the Shoulder Bag is small. Also, I LOVE LOVE LOVE the look of the Carly and would love a medium but again, I think it's too big for me. How do you get used to carrying bigger bags?? Do you just do it and get used to it?? Talk me into it so I can ask DH for a medium Carly for Christmas.