The Hunt: Knee-High Boots for Work and Weekend
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Today, let's go on a hunt for the best black knee-high boots! If you're unfamiliar with our Hunts…
Sure, we all know what wardrobe essentials for work professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.
We haven't gone on a hunt for boots for a zillion years (or so it feels) so let's go on one today. The problem with boots, of course, is that there are SO MANY really distinct styles. In the past we've gone on hunts for flat knee-high boots, heeled knee-high boots, weatherproof boots, flat ankle boots, shooties, heeled ankle boots, and block-heel boots. There's a lot to update and we're going to start with one we haven't done in a while: the tall knee-high boot.
Tall knee-high boots were supposed to have gone out of style several years ago. Yet: every store still sells them, and I still see women wearing them. I think tall boots work great for commutes (particularly in bad weather or cold weather), they look great with tights, leggings, and skinny jeans.
While tall boots aren't my first choice to wear with bootcut, straight, and cropped pants, I often find myself grabbing my skinnier pant styles anyway in bad weather, to better avoid slush and wet hems. I have a feeling (and I think a lot of retailers do as well) that a lot of women will be grabbing tall boots to wear with skinny pant styles this winter. (Funnily enough readers just had a discussion on this topic a week or two ago…)
As I've noted in the past, if you're trying to get a versatile boot to wear for both the weekend and work (when we eventually return to the office), I'd look for black suede or black leather without Western details like harnesses, with a toe shape that doesn't feel too trendy, and without too many buttons. I will also note that a leather boot is going to breathe a lot more naturally than a synthetic material, which means they'll be wearable for longer and more comfortable.
So, let's go on a hunt for the best black knee-high boots for work and weekend…
Our Latest Favorite Knee-High Boots For Your Commute
Hunting for black knee-high boots? Some of our long-standing favorites (as of 2025) include La Canadienne, Sam Edelman, and Sofft; also check this J.Crew bestseller, this Cole Haan option, and Vivaia for comfort.
Our Latest Favorite Tall Boots Under 2.5″
Stay tuned for a roundup of our latest favorite knee-high boots under 2.5″! As of 2025, Staud, Stuart Weitzman, and J.Crew both have nice options — and you can drool over these gorgeous ones from Totême.
Our Latest Favorite Heeled Knee-High Boots for Work
As of 2025, knee-high boots with a heel are back! Some of the best-looking options include these from J.Crew, Schutz, Veronica Beard, Staud, and Stuart Weitzman. If you're looking for an affordable alternative to try the style, check out these boots at Loft, or these boots at Amazon, both under $100.
Our Latest Favorite Weatherproof Knee-High Boots
Only interested in WATERPROOF options? These are some of our latest favorite weatherproof knee-high boots for work…
A Closer Look at The Best Knee-High Boots for Work
Sofft
These Sofft boots are waterproof and come in a zillion different colors and fabrics. I like that the laces make them adjustable, but there's also an inside zip — and this boot has been around for years.
We're picturing the flat option above, but there are some available with a slightly higher heel.
Another nice option from Sofft if you're not a fan of the laces: the Samantha boot.
Cole Haan
I love the textured leather backs to these Cole Haan boots, as well as the interior zip and padded footbed.
They've got a lot of nice reviews, and (woot!) are on sale — they're normally $300, but are down to $182 today. Nice.
La Canadienne Boots
La Canadienne boots are always splurgeworthy because they're experts in waterproofing — and these tall, sophisticated flat boots have 465 glowing reviews at Zappos.
I like that they come in three width options, are waterproof, and are available in black leather, black suede, and espresso suede. Nice! They're $525.
Prada
I like the lightly crinkled texture and almond toe to these boots from Prada — as well as the fact that the heel height is just under 2″, making it walkable but still giving you a bit of height. They're $1,350 at Nordstrom.
Ladies, please weigh in — what boots are you wearing this season? Which do you think are the best black knee-high boots for work and weekend?
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Updated stock photo (woman pulling suitcase) via Pexels / Gustavo Fring. Previous stock photo via Deposit Photos / tinx.
Late to comment but I bought the La Canadienne boots in black suede 6 years ago. The boots are still in impeccable conditions. I have wore them at the office and on the weekend for the past 6 years (I usually alternate with 1-2 other pairs of boots ) during fall and winter season. I live in Montreal, Quebec and there are perfect for cold and rainy weather. I am thinking that I should buy the black leather ones.
Not that being on trend is a priority for everyone but the look of knee high boots with skinny jeans looks incredibly dated and stale to me.