Ends of the spectrum

I don’t think that I have a defined sense of style. One day I might wear a crazy caftan, and the next a plaid pleated skirt with a black turtleneck. It’s usually more about what strikes my mood. Some days I’m daring and some days, not even close.

I recently ordered two pairs of shoes that are a great depiction of the opposite ends of the spectrum in my closet:

Classic penny loafers that reek of conservative.

Moccasin boots that are far from conservative.

Both pairs arrived the other day and I have to tell you, the moccasins are so comfortable it’s like you’re wearing slippers. I wore them to work with leggings and a sweater and felt like I was in my Pjs and slippers all day. I almost felt indecent! The penny loafers needs some breaking in, however.

Overall, I have a good handle on what I’ll wear the boots with. But aside from rolled boyfriend jeans, I have no idea what to wear the penny loafers with. Help?

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