18 Pairs of Fall Boots: A Review of the Good, the GREAT (and the So-So)

In an attempt to find the perfect fall boot, both in comfort and style, I tried on 18 different pairs. Today is a review based on comfort, style and versatility (for all budgets). All of these I liked visually for different reasons (some were a stretch stylistically for me) and while some proved uncomfortable or simply not worth it, there were definitely five stand out winners. I wore the same basic white top and jeans that I love for each of them (and a skirt for the tall ones) for the sake of keeping this experiment as controlled as possible (as this is VERY serious business). Here we go…

#1 Cloudy Waterproof Chelsea Rain Boots, $60

Verdict: Cute but kind of uncomfortable. I liked that these boots had a chunky sole and I generally love a Chelsea boot due to its easy slip-on abilities. Two weekends ago, when I had just got these, it rained and Birdie, the perpetual optimist, squealed and asked me to go jump in rain puddles with her. All the rest of my rain boots were up at the mountain house so I put these on and spent the morning in them. I can sadly report that they are cute, but a bit uncomfortable. It could be because I have wide feet, but I couldn’t wait to take them off and now sadly I have them forever (but might sell them on Poshmark).

#2 Forest Chelsea Boot, $175

Verdict: LOVE LOVE LOVE. These boots are cool, comfortable, modern/edgy and just generally so easy to wear. They are really skinny at the ankles thus they tuck into your jeans really well.

#3 Shanta Bootie in Black, $130

Verdict: LOVE. SO EASY TO WEAR.  These are comfortable, they elongate the leg if you are into that (it zips in the back and the ankle is really tight and slimming) the heel is the right size, and the shape is the perfect reference to the cowboy without being too theme-y.

#4 The Cowboy Boot, $475

Verdict: SPECIAL, AWESOME, THEY MAKE AN OUTFIT (but a splurge). My best friend works at The Great and she is WILDLY convincing of their clothes (which we’ve both loved since way before she worked there), so I get to borrow her stuff and test it out. These shoes do make a basic outfit cool instantly. They just do. They are expensive, but if you are going to splurge I highly recommend these over the next pair.

#5 Mallory Chelsea Flat Booties, $415

Verdict: Cool, but not worth it if you aren’t going to wear them all the time unless you have an unlimited shoe budget. I did like these, and in the photos, I like them even more but for $415, they need to be way more interesting to me (like the cowboy boot above) to splurge on. A great boot, would likely last a long time, but too expensive.

#6 Suede Wooden Platform, $229

Verdict: LOVE SO MUCH, QUITE POSSIBLY MY FAVORITE. A DEFINITE KEEP. I guess these sell out really fast, and I can see why. I had no idea how into the “shootie” I would be but that platform is so cool and warms up the faux black suede. It’s very fitted so it feels comfortable for how high it is (and the platform adds good support). We all LOVED these.

#7 Shanta Bootie in Snakeskin, $130

Verdict: LOVE and so easy to wear. I’ve worn these far more than you’d think. They dress up a basic outfit instantly (kinda like the cowboy boot does, but far more affordable). They are a good everyday heel height and the neutral tones of the faux snakeskin make it easy to mix into my wardrobe.

#8 Isa Boot, $198

Verdict: GREAT, but I love their Chelsea boots the best. I love Nisolo as you know, but left my Chelsea boots up at the mountain house and didn’t have time to order them for this shoot. I really like these, too. They have that cute grandpa thing going on, I just prefer the Chelseas because they are strangely elongating and listen, I don’t have time for laces these days.

#9 Kensington Chelsea Rain Boot, $70

Verdict: These are fine, but I would worry about the white sole. We thought these were cute rain boots and they are on the more affordable side at $70, but I feared that the sole would get dirty so fast, which was my favorite part about them. Although one of you has given me the hack of using Mr. Clean Magic Eraser to clean off the souls of my Vince sneakers, so maybe if you don’t mind cleaning your shoes all the time, these are for you.

#10 Zoe Chelsea Boot, $89

Verdict: THE FASHION CREW ALL WANTED (and some bought). These are awesome for the price and some of the team bought them right after. I’m still trying to dabble in the chunky heel trend (I lived through the first round of it in the ’90s) so the idea of making my feet look huge isn’t really my thing. But my team can attest that they loved them and they are very comfortable.

#11 Leona Heeled Boot, $160

Verdict: Not for me. I really tried, I did. I know that these Doc Martens are cool (call them Doctor Martens if you want to make anyone laugh) but they are like 3 lbs each and A LOT OF SHOE. We all know people who love a really heavy shoe and I do think that these can be cool, although I think we can safely say that I’m not pulling them off nor do I have the time to lace them up.

#12 Raakel Knee High Boot, $225

Verdict: Rad, but too specific, intense and loud to be versatile. This just isn’t for my life which usually includes running around, shopping or sitting and writing. I rarely take meetings that would require this vibe. However, I think pairing these with a midi dress or a basic shift would look great.

#13 Nestel Knee High Boot, $240

Verdict: Versatile, but pretty simple. I’ve had these boots since June but have only worn them a couple of times due to it being summer. I think the over-the-knee boots below are more “me” but these are really good. If I lived in a climate where I’d wear tall boots more consistently, I’d highly recommend these.

#14 Dorien Over the Knee Boot, $252

Verdict: GREAT. LOVE. I’ve worn so many times. SO MANY. They are comfortable, they stay up but are a tiny bit slouchy so they look casual (I hate super slouchy boots).

#15 Siren-3 Pointy Toe Boot, $125

Verdict: GREAT for dressier boots. Admittedly these do not look great with these jeans (but seriously, how great are those jeans???) but I really need some boots like these because I notoriously don’t have any dressy shoes and these are still on the quieter side. They come up the leg a few inches higher than you see there, so I’m not totally sure how to wear them which means I actually might not keep them.

#16 Indie Faux Leather Heeled Boot, $35

Verdict: SO great for the price. So simple and classic, and look very similar to Madewell boots, but for a third of the price. They are easy to slip on and have a great heel height.

#17 Hudson Waterproof Boot, $215

Verdict: Great, if you live in a cold/snowy climate. I thought these would be good for the mountain house and they are, but they are more of an investment so I’m going to try these from Target instead because it doesn’t get THAT cold up there and it doesn’t snow THAT much.

And lastly, a boot that I really love (and wear all the time) that I just couldn’t NOT share. I am wearing a different outfit (from last weeks post), but the pants are the same so I think it’s allowed:

18. The Regan Boot, $178

Verdict: Simple, versatile and classic. At first, I thought that these were boring and almost too perfectly brown, but once I styled them out in this outfit, I was like, oh no these are good and yes I’ve worn them a ton (they are especially cute with a dress and socks how I styled them last week).

Whew, that was a lot of boots, but SO FUN. Here are all the ones I tried in one place:

1. Cloudy Waterproof Chelsea Rain Boots | 2. Forest Chelsea Boot | 3. Shanta Bootie | 4. The Cowboy Boot | 5. Mallory Chelsea Flat Booties | 6. Suede Wooden Platform Boots  7. Shanta Bootie in Snakeskin | 8. Isa Boot | 9. Kensington Chelsea Rain Boot | 10. Zoe Chelsea Boot | 11. Leona Heeled Boot | 12. Raakel Knee High Boot | 13. Nestel Knee High Boot | 14. Dorien Over the Knee Boot | 15. Siren-3 Pointy Toe Boot | 16. Indie Faux Leather Heeled Boot | 17. Hudson Waterproof Boot | 18. The Regan Boot

Do you have any boots you love love love? Do you guys like these types of review posts? Let us know below. xx

*photography by Veronica Crawford