Comfy footwear is very important to me and for me. I have arthritic feet, and a re-torn meniscus. Re-torn in September (I'm toughing it out this time) after surgery to repair it just last February (that's why I'm toughing it out this time), because that's how I roll. Or fall, rather. I also apparently have very high, delicate arches, so I can't wear anything for too long without some good arch support. The orthopedic surgeon who repaired my knee last February actually recommended I wear at least a slight heel at all times if I don't buy specifically arch-friendly shoes, because apparently, they're more likely to provide support. Have I verified this? Nope. But there's that unsubstantiated tidbit anyway. You're welcome.
Anyway, many kinds of shoes, I am willing to spend more money on because of my special snowflake, entitlement-happy, high maintenance diva feet. Most shoes and boots, it doesn't matter how much I weigh, I can still wear them, so it's more worth the investment to me.
If it's wide-calf boots, I just get a as comfy as I can still saying in a reasonable price point. Some wide-calf boots can be around $200, and I just don't want to go there.
I like boots, though. When it's freezing cold and I really want to wear a skirt but I don't want to tromp through snow in heels, I have knee-high heeled boots.
When it's casual Friday and I don't feel like wearing trouser jeans - because sometimes oxfords, heels, and flats (my typical trouser-jean go-to's) just aren't doing it for me some days - I do skinny jeans and knee-high boots.
Sometimes, despite my "looks" preference for oxfords or heels with trouser jeans or dress pants, I want just the comfort of a pair of ankle boots. (Although this, I don't do as often, because it's kinda dancing a line, particularly with the dress pants. But I cop to having done it one day when I knew I was going to spend the entire day in the building's basement doing a page-turn and I couldn't be bothered to be anything but comfortable. And don't ask me why I think that's a line to dance, it's just a gut feeling.)
But where am I getting these things?
The knee high boots in particular are fun (please read that word sarcastically) to find, because I'm a size 10.5 or 11 regular (not wide, amazingly, although I can pull off wide) with 17" calves at the widest point. There are a variety of places you can get wide-calf knee-highs, but I tend to like Avenue's. The calves are about right, the heels are solid and not too high, and the styles are fun without being completely out of reach price-wise. The width and length are slightly on the big side. A 10.5 would probably work better, but very few places actually carry a 10.5 so I don't hold that against them. Still, the 11s are quite comfy.
And now LOOKIT THE PRETTIES! (And warning, I have a weird buckle fixation, so that will be a recurring theme in my shoe selections.).

The first two pair work particularly well with skinny jeans and a tunic.
The the pair on the left have an flex panel (you can see it best on the second on in) on the inside that has just a bit more give, which is really nice in case the pants are bulkier than you anticipate. You can find them here, in a choice of three colors.
The ones in the center just look awesome with any top because of the coloring. And I like that the two-toned is flipped from the typical two-tone (most I've seen are black on the bottom with the cognac color on the band), and I don't typically like to be ... well ... typical. They don't have this exact boot anymore, but they have one very similar here. And, well, honestly I like the re-design better, but I'm cheap, so I guess I'll just deal with the heartbreak.
The ones on the end are usually my go-to's with skirts. I also have them in brown. I don't do it often at work, but if you wear a skirt suit or good skirt/blouse/sweater/jacket/whathaveya combo to work with boots, it should really have a bit more of a heel to kick the look up a notch. This is a heel, but not a teetering heel by any means. This particular style doesn't appear to be available anymore, but Avenue carries this one, which is very similar.
Now, on to ankle boots. Ankle boots (flat ones, anyway, but heeled ankle boots will end up in a different post or this one will be nine miles long) are a rarity at work. But like I said, they were great on "stuck in the basement" day. And dang, they're just so comfy. They're good for casual Friday's and weekends, right? Right, so I'm including them.

The ones on the left are from Bare Traps. At size 11 medium, these are so perfect they fit my foot like a glove. Seriously comfortable. The black appears to be gone, but you can still get them in brown and dark gray.
The ones on the right are Earth. And if the Bare Traps I just mentioned fit like a glove, these fit like a glove that was custom-made for me. I wish they were slightly dressier, but dang, they're still beautiful on the inside. Plus, they've got character. If I were wearing these out to the museum on a Saturday and ran into one of my company's VPs while wearing these, skinny jeans, and an Igigi tunic, I'd still be cool and credible. In my own head, anyway.
Now, I have snuck in other things at work before that may have been borderline, but depending on the audience...

Okay, cowboy boots. While only on casual Friday's, and while wearing boot cut jeans and a nice, tailored blazer and crisp blouse, I have worn cowboy boots to work before. They're comfortable, all right? Completely wonderfully comfortable. Plus think about it, I live in the Midwest. I love 'em, and any company executive who's ever noticed I'm wearing them has loved them. So what the heck? I wouldn't advise this, however, any further east than Indiana, heh. These boots are several years old and you can't find them anymore, but this pair is very similar in theme and versatility. . Comfortable enough, I get the slight heel, and they last for freakin' ever. I had one pair that, I kid you not, lasted 15 full, heavy-use years.
Finally, on other comfy, snow days, I will occasionally break out my pair of Borns. These are unobtrusive enough I've worn them with jeans and with dress pants, and comfortably kept my grip in icy parking lots. Again, comfort. I mean it's Born, right? Borns are so danged comfortable I could walk for miles. My exact pair doesn't seem to be available anymore, but these are darned close and ... dang, I like the new ones better here, too. Bah. I ought to stop looking for links, I'm bumming myself out.
................
All right. I seriously debated whether to post this last pic (and admission). For years, I was morally opposed to Uggs. Especially the whole "I'm gonna wear Uggs with shorts and yoga pants!" thing. I think over-rich, obnoxious middle schoolers at a school in our old neighborhood burned me out a few years ago.
Still, everyone said, "But they're so comfortable, you'll love them!" And I screamed back at them in my heart, "I DON'T CARE!!!!!!" while I debated exactly how much I liked these people. (Yes, I can be judge-y, you've been warned.)
Well, after much cajoling, I finally broke. And I begrudgingly admit, they're amazing. They're so beyond comfortable, they make me cry tears of "diva feet" joy. Am I ever going to wear them to work? No. Ah hell no. Am I likely to wear them out and about? On weekends, yes. In the evenings, yes. Lord help me, yes. And the great thing about the knit ones is, even with my abundant calves, I can pull them up to knee height.
/sigh
So yes, I broke. I bought two pair on sale last February, about the time I had knee surgery, and they were actually amazing and I could walk/hobble on crutches with them quite comfortably.

On the upside, older brands, like these, tend to go on sale more often. The pair on the left doesn't seem to be around anymore. However, you can find something similar to them here. The knit ones are actually still available in various colors here.
So yeah. There it is. My secret (almost unapologetic) shame.
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