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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

Boot Review Lores 3

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

Emilyhendersonboots Flatforms

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

Boot Review Lores 11

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

Boot Review Lores 16

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

Boot Review Lores 21

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

Boot Review Lores 28

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

Boot Review Lores 36

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

Boot Review Lores 45

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

Nord Fall Lores 27

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:

Emily Henderson Boots

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

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4 years ago

I’ve been obsessed with finding the best fall booties lately so this post was perfect. But honestly, my number one take-away is that I need to buy those jeans! So good!

4 years ago

Not a boot but an inexpensive vintage (if from the 90s vintage) white prairie dress a I’m selling for a family member on eBay! It has had surprisingly little eBay traffic, but it really looks like something for an EHD reader! And would look cute with some snake skin or brown suede boots! (To small for me, or I’d buy it!).

Ehd team – delete if this is not ok…I’m not trying to self-promote, just trying to share a good deal!

4 years ago

Yes, please! Would love to see more posts like this.?

4 years ago

I love Saturday fashion posts. Cup of coffee and a bit of shopping and/or dreaming.

The best boots I bought this year were from Nordstrom called the Blondo Elvina (who names these things?) waterproof bootie. I bought them in a black croc pattern but they also come in a snakeskin pattern and other styles. They are really comfortable. And did I mention they’re WATERPROOF boots that actually look stylish and not like I’m about to go harvest apples. I have a pair of rain boots but on rainy days its nice to know I have a pair of dressy boots I can wear to work that won’t get ruined by the water. They were about $150, and I sized up a half size for my wide feet.

4 years ago
Reply to  LouAnn

Thank you for telling us about blondo. I need a cute boot that won’t be ruined by snow

4 years ago
Reply to  Nat

Second vote for Blondo. I have the Glenda (?) sneaker boots in Black and Tan and wear them almost every day!

4 years ago
Reply to  Nat

Blondos are great and you can often find them at DSW and Nordstrom Rack for a bit cheaper.

4 years ago

Love, love, love your fashion posts. But everything is always so spendy. Would love if you could incorporate more affordable picks!

4 years ago

#9’s look amazing! How do they feel when you sit down? Can you cross your legs? Do you have to keep your legs stretched out?
Can a reader answer this, because I know the staff generally don’t comment on the weekends?

4 years ago

I’m loving the Saturday fashion posts. I am not on either coast so these clue me in to what’s going to eventually be in here.

J. Renaud
4 years ago

What is the brand of the jeans you are wearing?

4 years ago
Reply to  J. Renaud

She linked to them on #15–

4 years ago

I *needed* this post in my life

Paula Carr
4 years ago

Oh, I think those wooden sole ones are so ugly. And not cute ugly either. Sad face.

Not crazy about the tractor treads on a lot of these others, but I can see how they would be really practical.

The Siren pointy boots are kinda cheap looking??

4 years ago

please please tell me about your necklace?
you had it on in the grandpa sweater outfit last week too!

4 years ago

I was on the fence about ordering the first waterproof Jeffrey Campbell pair but now I’m confident I won’t bite the bullet. LOVE the jeans though and surprised they weren’t more $$$!

4 years ago

I have the inverse opinion about statement shoes. I am far more willing to spend big money on a ‘boring’, versatile, incredibly well made shoe that I can wear all the time in a basic color (black, tan, brown, nude), than I am on a statement shoe (even though they may also be well made and wonderful).

4 years ago
Reply to  JC

I was thinking the EXACT same thing! I save my investment for classic, simple, long-lasting pieces. For anything more specific or trendy, I’ll buy the cheap version.

4 years ago

Love love love these posts. I bought snake skin pair after your post two weeks ago. And am wearing the jeans based on last Saturday.

I can’t justify buying more for my home so this is a great.

I could probably get some me more target Halloween goodies tho. Is there a post coming?

Susie Q.
4 years ago

I like that you include a variety of heel heights. I’m pretty tall, so if I wear high heels I tower over everyone. The high heels in your round-up would be a “no” for me.

4 years ago

Love these review posts as I am a designer and fashion hound. My go-to boots have been the Frye Veronica. I have the taller slouch boot in two colors as well as the shortie and have been rocking them for 8+ years. There’s nothing hot or trendy about them but they’re good, classic boots that never look outdated and somehow manage to get better with age.

4 years ago

I. Just. Love. You. ❤️

4 years ago

The Patti boot from madewell is a definite must have! You should check it out!

4 years ago

Thanks for the helpful boot review! I need those striped socks! Can you please send information on where I can buy them?

4 years ago

I’ll buy those cloudy waterproof rainboots from you! I have a narrow foot and live in Idaho so I need a good tread for snow. What size?

Kelsi jones
4 years ago

I can’t get the link to work for the wood platform boots? $229.00 Can you tell me we’re they are from? Love them all!!!

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4 years ago

I have read through your article and i was satisfied of the good information that you have contributed in your article! Thanks a lot for that beneficial article!

4 years ago

Can you do another post of the ones you loved styled different ways??!? maybe with the staff?!?

Mariya Zafirova
4 years ago

Omg, 12 are my favourite!

Mariya |

4 years ago

Did you guys sneak in little mini boots on the bottom left of the very first image with all of the boots lined up? Very sneaky but very cute

4 years ago

I just received my Shanta Boots that I ordered. You are soooo right….They fit skinny ankles. I have never had boots that look good on my feet and have shied away from ankle boots before. These fit great. I usually wear a 9 1/2 but got the ten. I do have a narrow foot too
Thank you Emily !! The hunt is over

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4 years ago

I have read through your article and i was satisfied of the good information that you have contributed in your article! Thanks a lot for that beneficial article!

4 years ago

As a recent convert to the Birkenstock brand (due to back and hip issues) I’m currently drooling over these selections. I miss a point toe so much.

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4 years ago

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