I've reached the end of my annual wardrobe budget, but I may make an exception to replace a fall/winter wardrobe essential. I have two pairs of old Clarks shooties that I think it's time to retire... the shape and heel of one pair makes the balls and arches of my feet ache as soon as I put them on (which is a shame, because they're cute and barely worn), and the other is slightly less uncomfortable but still not great.

I'm on the lookout for replacements that are more comfortable and won't look silly with bare legs/tights for skirts and dresses as well as pants, and I'm trying to figure out if this pair works on my scrawny ankles. There's a bit of a gap, but I *think* the slit helps mitigate the flowerpot effect... am I right, or is that just wishful thinking?

I sort of wish that they were slightly dressier, but they'll work for less-dressed-up business casual days, and smart casual. I'm also eyeing some sock boots for a dressier option that may hug closer to narrow calves/ankles, possibly the Free People find, in either the snake print ( love snake prints and would happily use this kind as a sorta-nude neutral) or black... if anyone has an opinion or experiences or alternative suggestions, I'm open to hear them!

UPDATE:

Thanks for encouraging me not to settle, all. I ventured into an actual physical shopping store for the first time in forever and tried on a bunch of options, and I think I have a winner: Naturalizer Daley (pictures 5 and on). There's still a tiny gap, but it's very slight. They're also very comfortable, the shaft material is super soft, and they have a heel that's just under 2 inches, so very walkable. I tried them with a bunch of skirts and I think they worked with all of them (only one photographed). And I think they work with cropped pants, too (shown). What do you think?

And as a bonus, I've also been on the lookout for about 6 months for a black-tie appropriate dress, so I don't have to scramble if an event comes up... this isn't factored into my budget, since it's a special occasion item that I intend to hold onto for a long time, and when I need it, I'll really need it. I happened to walk past a mannequin with this lovely silver cowl-neck dress (in the Finds), and it fits like a dream, so it followed me home. I need to get it hemmed a tiny bit, but otherwise it's perfect and checks all the boxes I love: elegant interesting neckline, it's simple but not boring, it can accommodate a regular bra (with some attention to strap placement), and the fabric is beautifully slinky and drapey.