I'm pretty sure you can as well. Are you going down to Saks tomorrow? Whitney was telling me about you getting the red expandable. I'll be down there after work tomorrow to pick up a bag and wallet.
Definitely, though I don't have a medium flap myself, but my DS 225 works perfect. I'm 5'4. I believe medium & 225 are more or less the same size.
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Thanks for your pics, you look really good with the reissue . But is the strap for the classic the same length as the reissue?