The other day I excitedly tried on a pair of boots that I had ordered online and was horrified by how uncomfortable they were. Stiff leather. Strange arch. Tight and painful. Does this company hate feet? Is this a sort of foot sadism fetish? Those boots shall remain nameless (I reviewed them very badly), but it made me want to find – and help others find – very comfortable walkin’ boots (cue the song). So I went shopping in person like I did for the sandals review (as much as I could), then ordered what I couldn’t find in person online to try. I tried on over 40 pairs of shoes. My wide troll feet were so excited and confused by the level of attention they got. I found so many comfortable walking boots that are winners (in all of the categories). Drumroll please…

A few caveats (per usual):

1. All of these are comfortable, and I put my stamp of approval on every single one. I’m not going to waste my team’s time (or yours) shooting things I don’t recommend. So while not all are a 10 in comfort, all of these are 7+ in comfort, and those that are a 7 make up for it in style.
2. I didn’t try on a lot of super cheap shoes. Unlike a blouse, boots need to hold up, and in my experience, quickly made synthetic boots last a season at best, but if I’m just being a snob and you’ve worn cheap boots that have held up, LMK. I tried a few $300+, but honestly they just weren’t worth the splurge when the below winners were better and more affordable.
3. I stayed away from hiking, snow, ski, or rain boots. These are just cool leather boots for fall, winter, and spring.
4. I bought all of these (and will return some). While I have some partnerships with many fashion brands (some seen here), nothing here was sent in exchange for coverage.

Best Western Inspired Bootie

Blazer | Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

Score – 7/10/8. I love that these have the western vibes, without going full cowgirl. The pointy toe and that heel edge up most outfits (even just a T-shirt and jeans).

Boots

Comfort: 7/10. Comfortable enough that if you have an urban job and commute on foot, you’d be fine for a mile. I would wear them for line dancing, but by nature of the shape of the toe and heel, they aren’t a 10.

Quality: 10/10. Continuing to be so impressed with Quince’s leather quality. It feels really thick without being too stiff (also, their site has so many reviews, which are helpful, so don’t just trust me).

Style: 8/10. Classic without a lot of extra bells and whistles, making them really versatile. Work, shopping, dinner – they just feel like the boots you can throw on when you are wearing something simple to show that you care about style.

Winner: Most Elegant And Flattering Suede Kitten Booties

Top | Jeans | Belt | Boots | Beaded Necklace | Gold Charm Necklace

Score: 8/9/9. These are really pretty suede booties, and I trust Sezane to bring the French vibes in a totally easy-to-wear way. More on the streamlined and elegant side (and probably less practical for some of us in the PNW or really wet areas).

Boots

Comfort: 8/10. The heel is short enough that you can cruise around all day. The leather is soft and pliable, warm and not stiff. Since the kitten is so kitten-y (small), you don’t feel 100% supported, so if you are a rushing-around-town walking commuter you might want something with more heel real estate to avoid an ankle twist. But for day-to-day, pretty dang comfortable (while fitted, it’s not compressiony at all).

Quality: 9/10. The only reason it’s not a 10 is because suede is more fragile than leather. But I really trust Sezane to make high-quality leather goods, so without wearing and testing for a long time, I’d feel really good about recommending these.

Style: 9/10. They fit under jeans (or any trousers) perfectly and could easily work with tights. They are fitted around the ankle (with some stretch and room) and are really slimming (if you are into that). Not going to lie, I loved looking down and seeing my famously wide feet look elegantly slender and long.

***I love this shirt, by the way, but it’s oversized so I’m returning it to get a size 2 (so size down).

Winner: Most Comfortable Block Heeled Booties

Sweater | Jeans | Belt | Boots

For my office ladies and walking commuters. These come in three colors and are the “wear all day and night” type of shoes. They are sock booties (sooties?) and are stretchy and tight and feel fantastic on. If you had to wear a heeled boot all day while you cleaned the house, this would be it.

Boots

Comfort: 10/10. The arch is perfect. The footbed is soft. The block heel is wide and short. And it really just feels like a glove on my foot. I felt lifted, supported, and extremely comfortable.

Quality: 8/10. The leather is so soft and amply thick for something that is meant to be inherently thinner and stretchy. But since it’s not a thick leather and they are fitted, I wonder if the toe will wear a bit with heavy wear. They are very well constructed, with the leather wrapping around the foot into a seam up the middle. They feel extremely high quality; I just think the thinner/softer leather might wear a bit (literally no evidence of this).

Style: 7/10. These are workhorse shoes (see comfort rating) and are really streamlined and simple, but they aren’t going to make the outfit. They are the comfortable supporting role. I bought these in the burgundy and returned them (because of the other burgundy boots below that are a 10/10 on all three), but I’m tempted to buy them in black as just go-to boots for all winter nights when I want a lift but don’t want to be extremely comfortable (great for dancing). They don’t read as “heels,” which is a good thing if you want to still give casual vibes. I think in black or brown they would be an excellent staple for any capsule wardrobe.

Best Tall Western Inspired Boots (That Aren’t $400)

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

Hot Take: Cowboy/girl boots are a cool vibe, sure, but they are specific, and every time I put mine on and try to wear them out in the city, I feel like a fool (just me, not judging, and this might be an age thing). Now THESE have that western shape and heel, but are way more polished and appropriate for more occasions IMHO.

Boots

Comfort: 6.5-7/10. They are comfortable considering they are a lot of boot and are more constricting due to thicker leather. The toe is narrower, obviously. But they are still really comfortable and easy to wear. Walking for a commute, for sure, if less than 10 blocks, but the dogs might bark if you wore them 8+ hours. More “going-out boots,” for sure. Leather is on the stiffer side.

Quality: 7/10. Steve Madden is a mid-price brand, and my experience with them the quality matches that. I returned these (I don’t need them), so I can’t attest to what I’m about to say, but my fear was that they would bend and crease where the ankle is. Now that might be fine for you, and maybe building a patina is what you want. But I loved how polished and high-end they look, and I feared that the crease would take away from that. The leather is really nice though, a bit on the stiff side with nice lining, and the heel feels solid without being too heavy.

Style: 9.5/10. I think these are really cool and would absolutely make a simple outfit look much more stylish. They would look great over jeans, with a skirt, or with denim shorts (i.e., festival vibes). If money or closet space is no object (lol), I think they are a great addition. The price is pretty great for how simple and cool the style is.

Winner: Best Tall Boot For All Occasions

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

These are my favorite, y’all – my top boot this year (ever?). I’ve worn them 15 times, and I just got them in August. I’ve worn them with jeans, with dresses, with leather shorts on our anniversary date to the Ritz-Carlton. Let me gush:

Boots

Comfort: 10/10. The shape of the arch is so soft, making them so easy to walk around in. The kitten heel is small enough that you don’t clock you are wearing “heels,” but I don’t feel wobbly at all. You can just slip them on easily, and I could walk for hours in them. That toe shape is slimmer, and yet it’s not constricting! Just feels like it fits.

Quality: 10/10. The leather is soft but thick. And I always worry about these types of boots slouching too much (which is fine, but not my thing), but these stay up with enough structure. It’s Italian leather (and they aren’t cheap for a reason), and it just feels supple.

Style: 10/10. They are so simple and cool, and that color feels perfect for this year (they come in black and brown, of course). They are flattering even with jeans and just pop out of the pant in a nice shape. And I love that they aren’t a high heel because sometimes that screams “I’M SUPER DRESSED UP FOR YOU,” especially in a short skirt, when sometimes you want to be more low-key about it.

Winner: Best Heeled Bootie For The Low-Key Crowd

Sweater | Jeans | Boots | Gold Charm Necklace | Purse

It’s embarrassing that after living here for 5 years, this is the first pair of Blundstones that I’ve tried on. And if I weren’t obsessed with the Pikolinos below, these would be my go-to heeled bootie. Blundstones last forever (10+ years), and these are the heeled version for those who want that little lift.

Boots

Comfort: 10/10. The footbed is SO soft. They are lightweight, and the ankle just curves around you in the best of ways. The heel barely feels like a heel. The elastic in the ankle provides extreme flexibility, and the bend of the toe was instant – no breaking in needed. I also love the double tabs – so easy to get on and off without bending down (your finger easily fits in both).

Quality: 10/10. Don’t try arguing with Oregon girls about the durability of this brand. Marlee and Gretch both have had their Blundstones for over 10 years (Marlee since high school). And these are boots that do look better with patina, so it’s a long-term purchase you can feel fantastic about.

Style: 6.5/10. They are not necessarily additive to an outfit, but you throw these on when you are in the mountains at a bar with a flannel and jeans, and you can dance all night long because they are so dang comfortable. (I think I just talked myself into keeping these – I want to do that!!!).

Winner: Best Block-Heeled Camper Boots (The New Frye?)

Sweater | Skirt | Boots | Beaded Necklace | Gold Charm Necklace | Purse

These are fantastic and definitely a new staple for me. They balance the trend in a more elevated way and are so easy to dress down (I can already envision our family pumpkin patch picture in these, denim shorts and that Sezane plaid top from above).

Boots

Comfort: 7/10. These are on the heavier side – not as heavy as Frye boots or even close, but the leather is stiff, and the block has to support the leather. So they are a lot of shoe. They are easy to slip into, and you can cruise around all day in them with a roomier foot. But you are very aware that you are wearing boots, if that makes any sense. The footbed could be slightly cushier if I’m being picky.

Quality: 10/10. The last pair that I bought of this style from Madewell creased really badly in the first year, which is fine for that more rugged, worn-in look, but these feel so thick and solid that I think they’ll patina in tone, and I feel confident they’ll keep their shape and not be slouchy.

Style: 9/10. I love how elevated they look in this more monochrome look (the almost matching heel and leather). These are super classic; they aren’t reinventing the style or adding to it (which I think is what Quince does so well – they don’t try to be really trendy, which is a good thing). It’s just super high quality and timeless and at a more affordable price point without being boring. Yes, I partner with them at times, but no, this is not one of them, and I paid for all of these shoes.

Best Waterproof Chelseas

Jacket | Pants | Hat (unavailable) | Boots

I love this brand and how everyday but cool they are, and that they are waterproof without being rubber.

Boots

Comfort: 9/10. Roomy. Soft footbed. Low/no heel. Stretchy, flexible ankle. The only reason I’m giving them a 9 instead of 10 is that the leather near the ankle is stiffer than, say, the Bludstones, but I honestly think it’s going to break in. I think that’s because this leather is waterproof and inherently stiffer.

Quality: 10/10. I have no doubt these will last for years, if not decades. They are thick, well-made, with a hefty, rugged sole and just feel like they are never going anywhere.

Style: 10/10. For the style. I think they nailed the proportions and the patina. And I think this style could also look really cute with chunky knit socks and shorts (think The Great). They won’t make the outfit on their own, but they lend a vibe that says you are outdoorsy but cool and ready for anything.

Winner: Most Comfortable Dressy Bootie (And My Go-To Booties)

Sweatshirt | Jeans | Boots | Beaded Necklace | Gold Charm Necklace

This brand is special. I bought my first pair of Pikolinos 10 years ago and wore them almost every day in Arrowhead during lockdown, cruising around the woods behind our house, loving that they felt like sneakers but hugged my ankle enough to not let leaves down into the shoe (not these). Like those, these are shockingly lightweight and comfortable. Once on, you don’t feel like you are wearing shoes and definitely not heels.

Boots

Comfort: 10/10. Undeniably extremely comfortable. So lightweight and flexible. Soft footbed. I’m not saying you would run a mile in them, but you definitely could. Rubber sole for grip, non-slip. It’s a joy to wear these shoes inside or out.

Quality: 10/10. Pikolinos are Spanish leather, I believe, and the construction is seriously good. My other pair lasted for so long (they are still in Arrowhead, and I’m going to try to find them this weekend!). I don’t know how this leather will patina, but they feel richly dyed, meaning they won’t scratch and leave a big light mark. The heel is wide and soft, and the stitching makes them look as expensive as they are.

Style: 10/10. They aren’t doing anything new or trendy, but the proportions are great, and the contrast in tones is perfect. They walk that line between utility and dressy, but I’ll most likely wear them daily out and about when I want to look a little elevated with a lift, but I mostly want to be just extremely comfortable (think all-day shopping shoes, all-day working, just the shoes you don’t have to THINK about). The toe is flattering and slimming, which would look great with skinny, flare, or wide-leg jeans. Yes, they are splurgy. Yes, they are worth it if it’s in your budget.

While I tried on a ton, if you guys have any that you love love love love love, please leave them in the comments.

*Photos by Kaitlin Green