Unless stated otherwise, all sizes in this article are listed in women's measurements.
1. A pair of Chelsea Boots because they're versatile enough to be worn year-round and go with almost anything in your closet. A must-have staple that will stand the test of time.

2. Thigh-high chunky heel boots to pair with a dress, skirt, or even leggings for an added dose of flair. You'll be showered with compliments, and there's no doubt you'll be wearing them for years to come.


3. Lucky Brand ankle boots for a style that's cute, straightforward, and enduring. You’ll definitely feel ~lucky~ to have these in your wardrobe.


4. Sorel Caribou boots are an absolute must-have if you're in a cold climate. Reviewers rave about these stylish boots for their exceptional warmth and insulation each winter (and yes, you’ll be wearing them every winter for years to come).

5. Over-the-knee heeled boots are a must-have, as reviewers rave about their comfort and ease of wear, making them a pair you'll actually want to wear season after season.


6. Doc Marten combat boots that will brave rain, sleet, or snow without compromising your pop-punk style. Docs are a timeless choice for a reason!

7. If you're into the classic Doc stitching but prefer a no-lace style, try a pair of Dr. Martens Chelsea boots. These boots slide on effortlessly, giving you all the style with zero fuss.


8. These chic brown boots are designed with a clever V-shaped elastic, ensuring they slide effortlessly onto your feet for a sleek and fashionable look. Reviewers rave about their comfort and versatility, making them easy to dress up or down.

Highly recommended review: "I've been wearing these boots for a few years, and they are the most comfortable pair I've owned." They are versatile enough for both casual and more formal occasions. I absolutely recommend them! I usually wear an 8 in running shoes but opted for a size 9 since I found it better when wearing wool socks." —Catherine
Available for purchase from Nisolo at $212+ (sizes 5–11, in seven different colors).
9. These chunky ankle boots come with over 10,000 glowing 5-star reviews, so they're definitely a trustworthy choice. What makes them so popular? They're said to be super comfy, supportive, easy to walk in, and simply gorgeous!


10. Over-the-knee boots designed intentionally with a wider fit and larger calves because everyone deserves to rock a pair of bold, fierce boots like these. They even come with an adjustable back tie to guarantee a *perfect* fit.

Promising review: "I had these boots years ago in a lighter sand color, and I was absolutely in love with them, then outgrew them… I was ecstatic when I saw them back!!! Got them today, and they’re perfect! Even for my extra extra wide calf. :)" —KMUR0789
Get them from Torrid for $72 (originally $89.90; available in sizes 6WW–13WW and in two colors).
11. Glove boots designed to wrap your feet in a cozy-chic embrace, exactly what those cool autumn mornings demand.


Promising review: "I’ve owned these in three different colors over the years, and I wear them all the time. They match with everything, are incredibly comfy, and easy to walk in. Totally obsessed!" —HJ889790
Grab them from Everlane for $150 (available in sizes 5–11 and in four colors).
12. Low wedge booties that give you just the right amount of ~lift~ while still allowing you to walk long distances comfortably. These little beauties are perfect for the job.


13. Knee-high boots featuring a hidden faux fur lining — just enough to add a bit of warmth when it's chilly but not so cold that you need to reach for the bulky winter boots.


14. Chunky over-the-knee lace-up boots because there's no reason laces should stop at the ankle. Now you can tie even more style into your fall (and winter) outfits.


15. A pair of lace-up combat boots that will stay with you... or rather, on your feet... year after year, no matter what life throws at you. Always a great idea to have a pair of sturdy, reliable, and versatile boots like these in your wardrobe.

16. Lace-up suede boots with a cozy fur lining, perfect for those days when it's just a bit too cold for combat boots and wool socks. No worries! These will come to the rescue.


17. This waterproof Sorel pair features a one-inch platform, slip-resistant soles with traction, faux-fur cuffs, and a warm microfleece lining. It’s no surprise that one reviewer has owned a pair for over five years.

18. These Hunter's short rain boots will keep your feet dry (and fashionable!) no matter the weather — even in the snow! Reviewers recommend wearing thick socks, but they’ll keep your toes warm and cozy.


Tommy Hilfiger equestrian boots are a timeless style staple, ensuring that you won't need to worry about them becoming outdated anytime soon. What's even better is their durability, built to last well beyond a single season.

If you're aiming for a 'hiker-chic' look, these Kodiak leather boots are perfect. They offer durability and ruggedness, much like any traditional hiking boot, but with a fashionable edge.


A pair of Minnetonka fringe boots that exude a boho-chic vibe. Crafted from soft, premium suede, they offer the comfort of slippers while ensuring durability for years.


A highly rated Columbia hiking boot designed to support your adventures with excellent traction and style. Reviewers are amazed at how comfortable, waterproof, and long-lasting they are, especially considering their lower price compared to other hiking boots.

Blundstone Chelsea boots, perfect for any activity you have planned: A morning coffee stop? Done. An afternoon hike? You bet. After-work drinks with colleagues? Of course. These boots will quickly become your new favorite footwear (and for good reason)!

Platform knee-highs designed to help you stomp around with full attitude. Will people mistake you for an underground alt-rock star? Oh, absolutely they might.

Sperry duck boots designed with a seam-sealed construction to keep moisture out, ensuring your feet stay dry and warm. I don’t know about you, but I prefer to keep my feet dry all year round.


26. A insulated memory foam snow boot to keep your feet warm and comfortable during all your upcoming cold-weather activities, from sledding to snowy walks! Reviewers love these for wintertime (and I hate to break it to you, but winter is coming).


A pair of quilted knee-high boots featuring buckle and zipper details. They're more exciting than your average boot while still being casual enough for everyday wear. They strike the perfect balance between a statement piece and a wardrobe essential... and I absolutely love them.

