Unless otherwise specified, all sizes in this post are listed in women's.
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I walk everywhere, used to go dancing as much as possible, and am overall really hard on my shoes — these boots, sneakers, runners, and clogs have stood the test of time.
Unless otherwise specified, all sizes in this post are listed in women's.
I grew up in Florida but went to Boston for college, where I experienced my first winter ever with these as my first real pair of boots. While having combat boots as your only winter shoes could be considered misguided, they honestly did me very well, especially considering it was the year of the "Polar Vortex." Paired with thick socks (like the Extra Heavy Crew from Smartwool), they are a formidable enemy to the cold and in my experience really keep out moisture. But of course, Docs are much more well-known for being the go-to boot for cool people everywhere, and they indeed make me feel VERY cool while wearing them. Sturdy as an ox, they will likely outlive me, especially if I get new insoles for them every now and again. I've had this pair for eight years and though they look worn — that's part of the fun! — they are in amazing condition. The sole is still 100% intact, no seams have ripped, and the leather is only getting more supple and comfortable with age. Everyone needs one pair of Docs. These are technically the Pascal boot, but you should check out their original 1490 boot and look at all of their styles.
Get them from Dr. Martens for $150 (available in sizes 5–11 and two colors).
The level of comfort in every Dansko shoe is nearly incomprehensible. The insole is somewhat hard, but in a remarkably good way that almost massages the arches of my feet when I walk. It's a unique feeling that requires a little getting used to, but once I did, holy moly, it was an eye-opening experience of what shoes can be. I know that sounds dramatic, but I'm not alone — the cult-status of Danskos is real and well-deserved. If you've been struggling to find a shoe that fully supports your feet all day, give these a try. They definitely don't look like they'd be the most stable, but I never feel more sure-footed than when I'm in my Danskos. These are my newest Danskos at a year and a half old, but looking at the sole, leather, and sturdy buckle, you know they're just at the beginning of their long life. I've yet to try Dansko's original clogs, but am running out of excuses not to!
Get them from Amazon for $94.99+ (available in sizes 5.5–12 and eight colors), Dansko for $135 (available in sizes 5.5–12 and three colors), or Nordstrom for $134.95 (available in sizes 5.5–12 and three colors).
I'm bad with high heels but always want to be a little ~elevated~ when wearing nicer outfits, and these were the answer. They give me the elongated line I'm looking for with their heel, but they're truly just as comfortable as my sneakers. Yup, these have the same incredible insole as all Danskos, but in a modern style that truly goes with everything. Back when we could go dancing, these were always the obvious choice for me. And I don't mean stand-around-and-try-to-look-cool dancing — my friends and I go DANCE. These have held up to about two years of stomping, nonsense, and crowded dance floors — even the beautiful wood grain detail on the heel is still in perfect shape!
Get them from Amazon for $94.89+ (available in sizes 5.5–12 and four colors), Dansko for $140 (available in sizes 5.5–12 and two colors), or Zappos for $96.01+ (available in sizes 5.5–12 and two colors).
These are great everyday boots that look amazing with basically everything and really ~elevate~ whatever you pair them with. They took a little time to break in around the toe box for me, but it really paid off, as they now fit like a glove...or...like a shoe that just fits really well, I guess. I've had these for probably close to two years, have walked in them *so* much, and they're still in incredible shape. I anticipate getting at least two more years out of them as-is — they don't even seem close to needing to be resoled yet, but I definitely will do so when the time comes. They are definitely an investment, but considering I used to pay about half as much for boots that would poop out after one year, I consider them well worth it. I recommend going up a half size from what you usually wear for the perfect fit.
Get them from Nisolo for $200 (available in sizes 5–11 and four colors).
I really wondered if these would live up to the hype, but the answer is a resounding "yes." I've had them going on three years, have put a TON of miles on them, and they're somehow showing no signs of aging. They stay shockingly clean, are super light, and are of course mega comfortable, which is what skyrocketed them to fame in the first place. They're even machine washable, a quality I thought was going to have to use all the time because of their wool exterior, but they've never seemed dirty enough to warrant a wash! I used to love them especially for days when I was traveling, but I also love them for bopping around the neighborhood and even wearing around the house when my feet want some support. When I got them I thought they'd be a little niche, but I throw them on for more occasions than I would have ever imagined, from grocery runs to grand adventures. I got a whole size up from what I normally wear and they fit perfectly.
Get them from Allbirds for $95 for women's sizes (available in sizes 5–11 and eight colors) and $95 for men's sizes (available in sizes 8–14 and nine colors).
Vionic puts a lot of work into their insole technology and it really shows — case in point, they made a heeled cowboy boot I could walk literally all day in. That's pretty miraculous. The white really pops with a ton of outfits and did I mention IT'S A COMFORTABLE HEELED BOOT?! Similar to Danskos, Vionic shoes have a very arched insole but these also have a fair amount of cushioning, which is especially necessary for the metatarsals when wearing a heel. These boots are only available in white, so if you're *super* sensitive to shoes getting dirty, these may not be for you, but mine still look pretty crisp after a year and a half, as many smudges just rub off. I recommend looking through all of Vionic's shoes since they really do it all, but especially their heels and boots if comfort has ever held you back from getting *just* the style you want.
Get them from Vionic for $84.99 (originally $169.95, available in sizes 5–12).
I was never really a tennis shoe person, but then I moved to New York and needed to become one because of the whole "walking everywhere" thing. These are really comfy, go with everything, and are all-around a great shoe. I'll be buying a new pair when mine finally give out (from no fault of their own, I've just put an INTENSE amount of miles on them in the two years and change I've had them).
Get them from Amazon for $59.95+ (originally $80, available in sizes 5–10), Zappos for $79.95 (available in sizes 5–11 and four colors), or Nordstrom for $80+ (available in sizes 5–11 and four colors).
Three years ago I decided I was going to "become a running person" and headed confidently into a specialty running shoe store to be fitted. I was highly recommended the Brooks Ghost series and took the bait. I'm so glad I did, because these shoes have done right by me ever since. I haven't become a "running person" but when I DO run my footfall feels soft and the shoe feels springy — like it's actually helping me run. Luckily, this is also a helpful feature for other physical activities I enjoy way more! I'm pretty sure my pair is technically the Ghost 11 and Brooks updates the model pretty frequently, so the shoes available for purchase are the Ghost 13, but according to reviews, they are also phenomenal. I think I'm gonna upgrade mine next spring and perhaps *sigh* try to become a runner once more.
Get them from Amazon for $105.85+ (available in sizes 5–13, including wide sizes, and 18 colors) Brooks for $130 (available in sizes 5–13, including wide sizes, and 11 colors), or Nordstrom for $130 (available in sizes 5–13, including wide and narrow sizes, and eight colors).