I love the boy bag!! I have 3 sizes (new medium, old medium, & small- all in caviar).
I love this style as an everyday bag because I mainly wear my bags crossbody & the boy has a good crossbody length for me. I’m only 5’ so strap length can be a dealbreaker. Plus I like the fact that I can wear the boy bag doubled up as well.
The new medium fits a lot & the strap length feels shorter. It’s roughly comparable to a 226 for storage capacity. It is a bit bulky on a shortie like me, but I love it for days when I need to carry more.
The old medium is the classic size that everyone else loves- except me! I bought it because it’s the most popular size but I wish that I bought the small. Storage capacity is relatively good. But I still end up using a card case because it’s hard to fit a mini pochette, wallet, & phone & car fob. And I find this size as still a little bulky when worn crossbody.
The small is my favorite size. It looks sooo flattering!! It’s perfect for crossbody. I find the strap length the longest, but it still works because the bag itself is very compact. Storage is minimal. I use a card case & the back flap pocket for extra cash/cards. I can fit in my essentials, but I cannot use a pouch/pochette. (Card case, key fob, perfume, tiny compact, lipstick, tiny floss, mask, 1 folded tissue, & regular iPhone all fit directly in bag).
I don’t like the classic minis (as my favorite bags) because they only have 2 grommets and lambskin leather options. I find that I miss the shoulder carry option too much. I also don’t like the 19 (as a favorite) because of the strap length, lambskin, & lack of structure. I think that I would like the mini reissue slightly more than the small boy if the reissue came in non-distressed leather options. (The mini reissue fits more than the small boy).
Go to the boutique and try on a lot of different styles & sizes. You may be surprised with your ideal bag.