Carter, it's so interesting to see your shoe choices! The mink loafers are adorable, but what got my attention are the pewter loafers! It has a very streamlined look and seem to work well with straight legs!

Thanks, MKK. The mink loafers fit right in with my style. The pewter ones don't, but boy are they comfy. I agree they work well with the straight legs. So, I'm thinking low vamp or super high vamp is the way to go. The two Born booties came today. I'll do a K/R on those whe the Pettys and the other loafers arrive. Shoes didn't use to be this challenging;-)

Carter, I've become a straight leg jeans wearer recently, and I can tell you that super high vamp is the way to go! For some reason it's just very leg-elongating and streamlined. The mink loafers also have that effect too, though and there's nothing stumpy about it!

Would sooo love to see the Born booties!

It looks like you've been having fairly good luck with shoes! I wish I could say the same for me!

LOVE the pewter shoes, with the mink loafers a close second.

My Steeve Madden Chelsea boots are workhorses, and going on their 4th year. They are low heeled, leather with elastic gores, and super comfortable to wear. Great with lean pants, but the almond toe isn't as good with loose and flowy trousers...pointy toes, even flats work better.

The zipper on my Russel &Brommley Chelsea boots broke, so I am kind of off zippers on footwear.

Carter, how to you feel about a lace-up Oxford?

Carla, glad you like the pewter and mink shoes!

I wish I could wear Chelsea boots, but honestly, even most zippered boots still require my toe to bend to a tear-inducing degree.

I just don't know about oxfords. I wore them for years with a plaid jumper, peter pan collared top and navy knee socks. That's a hard association to overcome;-)

Love #1 loafers. I hope 1/2 size up works for you because they are gorgeous - and I am sure the color is even better in person.
The Pikolinos boots are fun. I don't think there is a flower pot effect here and they are slouchy style and not close fitting. However is wearing them with skinnies only is good enough for you?
The pewter loafers are fab too!

I love the mink and pewter loafers. The pewter ones have the benefit of being high vamped enough that you can easily wear socks with them when needed. I may be in the minority, but I also like the brown ones, and think the sliver of exposed skin is flattering, but the vamp is high enough that you could also get away with socks here. And I really like the silver, but not if they don't fit...

I'm in Atlanta, too. And because I walk to work, I wear a lot of flats. I also struggle in fall/winter because I much prefer either the leg lengthening of a heel or the slimming structure of showing off my calves and ankles. So I share your sartorial pain if not your physical foot pain.

Glad to see you're trying out the Pettys (if they don't work with your feet, a search for them on Amazon will show you other brands with basically the same style). I find that I can wear my Pettys with low invisible socks and exposed ankles in the same temp ranges (or cooler) as covered ankles and sockless feet. I've also been known to wear them with cute striped socks and rolled jeans or straight leg trousers, but not sure how that will go over in your field.

For January and February I move into skinnies with flat boots, leggings and tunics with flat boots, and skirts with tights and flat boots too keep warm and dry. It gets tedious, but then suddenly we get that 70F day in February and I get to put on some pointy toed flats joyously.

ATLynn, you totally get it! Hoping the Pettys will work. Will do a K/R on all the booties when they arrive.

I haven't read all of the responses yet, but I love the shoes shown in pictures 1-4. The rest I don't feel as positive about. The clogs due to the pant leg grabbing issue, the non-leather shoes due to non-leather. I've tried synthetic shoes a few times and they always end up in the donation bag, quickly. The Pikolinos could go either way, they might be fab if you had the right pants to wear with them. The Kelsi Daggers I would avoid. I have a pair of KD sandals and after only a few wears, the leather separated and the heels and toes became unacceptably scuffed. So I'm a bit down on this brand at the moment but mine could be an isolated experience.

CocoLion, great input on the Kelsey Daggers! I've never even heard of this brand.