WIW - keep the loafers?

Today was chillier than it has been -- hooray! Another chance to wear a sweater. I put together a FFBO: Allsaints Drina cardigan, a black tee, and my slouchy Zara jeans. Plus bonus photo of my cat, who follows me wherever I got.

My actual outfit had flat boots. But in the photos, I'm wearing a pair of gorgeous Rag & Bone classic penny loafers I found at Nordstrom Rack yesterday. They would be an expensive impulse buy, so I am not at all sure I'm keeping them.

-They fit! I have never before found a loafer that fit the big bony bump on top of my feet (where the tongue is). 
-They are masculine in a way that I like. More feminine loafers don't fit my style (or my feet).
-They stay on my feet and are comfortable.
-They have brown leather soles. I've wanted shoes with a bit of brown to look more vintage-hipster-Madewell and less urban than my all-black shoes.

-They're preppier than my usual look. I grew up in Connecticut and boy do I know preppy. It's not my usual style, but I don't dislike it.
-They are somewhat similar to the men's oxfords I've been wearing a lot.
-Despite what I said about masculine being good, they do look rather clunky on me.
-I have a lot of shoes. (https://www.pinterest.com/monochro/on-my-feet/)

I have three pairs of flats, but I never wear them because they just don't stay on my feet comfortably. This might be better for my work shoe needs. They'd look fine with relaxed skinny or straight jeans. What about wool slacks?


Go to the full post to see all of the pictures →