I noticed that a big wardrobe hole is a dressy-ish black boot that I can wear to work. I was initially thinking to go for a Report Marks alternative, but the Clark's I ordered with that in mind didn't work for my feet. I also would have loved a black version of my Frye Julias, but those aren't around anymore. These are Timberland, and super duper comfortable, just like my other Timberlands.
Do you think the slight ankle bagging makes them too casual or stompy? Or just unflattering? I want something really simple and sorta sleek to go with outfits like this, which can't handle a lot more personality.
You'd think I'd be able to tell for myself, but I have notorious boot blinders.