So here is my two cents 
. I’m 5’3.5” tall and 102-110 lbs (ok, I’ve been snacking all summer) and have owned a few retourne Kelly 35s, mostly because I needed the larger capacity to carry legal documents with me. It was really work necessity that drove me to the larger sized Kelly, but I did feel like I was wearing a messenger bag when I would wear my K35 crossbody and the width of the crossbody strap didn’t make a difference aesthetically. I didn’t want to look like I was wearing a messenger bag when going to the office so I preferred to hand carry my K35s which made me feel more lady like and feminine, albeit still a casual look given the retourne style and 35cm size.
I would save wearing K35 crossbody for occasions when I wanted to look casual and sporty, always with jeans or pants, never with dresses, skirts or even shorts.
I noticed that even a K32 worn crossbody can look like a messenger bag and give off a sportier vibe whereas a smaller K28 still looks like a handbag whether it’s hand-carried or worn crossbody.
My advice would be to pick the size that you need to function, and then you can figure out ways to wear that particular size to create a more feminine look, sporty look, etc. At one point, I needed a Kelly 40 retourne for the capacity. After admitting to myself that I needed this size for work documents, then I figured out different ways to wear the 40 to look more or less casual, sporty, lady-like. So for me, rather than trying to pick a Kelly based on what size looks best on my body size and type, my recommendation is function first, aesthetics second.
Truth be told, there are ways to successfully pull off carrying a Kelly in any and every size regardless of stature.
Here I am with my K40....
. I’m 5’3.5” tall and 102-110 lbs (ok, I’ve been snacking all summer) and have owned a few retourne Kelly 35s, mostly because I needed the larger capacity to carry legal documents with me. It was really work necessity that drove me to the larger sized Kelly, but I did feel like I was wearing a messenger bag when I would wear my K35 crossbody and the width of the crossbody strap didn’t make a difference aesthetically. I didn’t want to look like I was wearing a messenger bag when going to the office so I preferred to hand carry my K35s which made me feel more lady like and feminine, albeit still a casual look given the retourne style and 35cm size. I would save wearing K35 crossbody for occasions when I wanted to look casual and sporty, always with jeans or pants, never with dresses, skirts or even shorts.
I noticed that even a K32 worn crossbody can look like a messenger bag and give off a sportier vibe whereas a smaller K28 still looks like a handbag whether it’s hand-carried or worn crossbody.
My advice would be to pick the size that you need to function, and then you can figure out ways to wear that particular size to create a more feminine look, sporty look, etc. At one point, I needed a Kelly 40 retourne for the capacity. After admitting to myself that I needed this size for work documents, then I figured out different ways to wear the 40 to look more or less casual, sporty, lady-like. So for me, rather than trying to pick a Kelly based on what size looks best on my body size and type, my recommendation is function first, aesthetics second.
Truth be told, there are ways to successfully pull off carrying a Kelly in any and every size regardless of stature.
Here I am with my K40....
