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The Best Fall Boots We Have And Love + Some Fresh New Picks We Want To Try

I feel like we keep declaring “fall is here” and yet it has only just started to feel like it here in LA (case in point it’s currently 66 degrees as I am writing this AKA freezing by our standards). While Emily has been donning boots for a while over in Portland, us LA gals are only now dusting off our tried and true fall boots. So when we were brainstorming fall fashion posts, we came to the realization that each of us has at least two boots we wear year after year. So without further ado, here are our favorites plus some fresh new picks that we are eyeing.

Let’s start with the fall boot queen, Emily Henderson herself:


photo by veronica crawford | from: my ultimate list of tried and true fall shoes

Boots | Shirt (similar) | Pants | Bandana

At first, I thought these Dr. Martens were too ‘young’ for me – it was two years ago when the clunk was just coming back (or maybe it had been around for a while) and I was like ‘THIS IS A LOT OF SHOE’. But over the last two years, I have worn the hell out of them. I normally roll my pant legs like this, OR wear with shorter pants because I find that if I don’t they look kinda dumb under baggy pants (I know that’s a thing but it’s not a thing for me). They feel totally classic, a throwback to my teens and at the same time fresh and young. I’m a fan. 

photo by veronica crawford | from: shopping my closet for fall & wearing some (ethically made) shoes that I love

Boots | Jeans | Sweater

The Nisolo Chelsea boots are SO GOOD. Buttercup chewed up one of them so I need to order new ones and with Oregon’s rain issue I don’t know if real leather is in my future for more practical shoes like these But when I lived in LA I wore these 2-3 years in a row during fall/winter (not gonna lie, we are going to miss LA in January/February SO MUCH). 

photo by veronica crawford | from: 18 pairs of fall boots a review of the good, the great, and the so-so

Boots | Jeans | Button Up

I wore these in the boot roundup post from a couple of years ago and they were a three-season boot at the mountain house. They are tall and fitted, but not tight so great for chomping through leaves. Then since they are waterproof I wore them like much warmer rain boots and often in the snow (not if I was playing in the snow, but definitely walking in the snow). I just bought another pair for up here because I loved then so much and left my first pair in the mountains (almost the only pair I left there because I wore them that much). I know they aren’t that cute, but they are so comfortable, versatile, durable, and high quality that I found myself opting for them over almost any boot. 

Here are some new options I’ve very temped by…

1. Blundstone Original 500 Series Chelsea Boot | 2. Brex Chelsea Boots | 3. We The Free Montage Tall Boots | 4. Montage Tall Boots | 5. All-Weather Amalia Boot |6. III Hiker Duck Boot


Boots | Jeans

Up until last year, I forgot how powerful I feel when I wear a really badass, almost punk-like boot. Living in New York was probably the last time I felt that feeling so it’s been a minute. There’s just a “don’t mess with me” vibe that feels antithetical to my general sunny disposition that I love. I think it fills the same part of me that wanted to play villains in my theatre days. Let’s call it balance? So when “the lug sole” boot was popping up hard in the mainstream last year, I decided to give it a go even though I was unsure. The phrase, “Jess, I don’t think you can pull these” kept repeating in my head. Alas, they arrived, I slipped them on and I immediately felt powerful. So if you are in need of a “power boot” but are worried they might be “too much” or “you can’t pull them off” YOU CAN AND GO FOR IT. Worst comes to worst and you return them… but I bet you won’t;)

Here are some others I really like!

1. Paloma Barcelo Ebba Platform Ankle Boots | 2. Madisha Chelsea Boot |3. Empire Platform Boot

Boots | Jeans

When I bought these month two into the pandemic, I didn’t really know why because where was I going?! But they were on a GREAT sale (Thanks, Mal) so I did. Now that I’ve been able to go out with friends and on dates, they have been one of my best/favorite purchases in a while. I truly wear them all of the time. They make any outfit look cooler and are pretty comfortable. I wear them like in this photo (jeans and a simple top) or pair them with a fun patterned dress to really get crazy. Moral of the story is to say yes to the “fun boot”! It’s such an easy way to make you feel cool and dare I say fashionable. O and I could only find these specific ones used on Poshmark so if you are looking for them they are called 1.STATE – Kelte Pointed Toe Leather Bootie. Good luck!

Should I get another pair??? I’m pretty into these:

1. Lima Mustard Python | 2. Jojo Pointed Toe Bootie | 3. Caty Chain Bootie


Cowboy Boots (similar) | Jeans (vintage) | Shirt

I may live in a city but I am a country girl at heart. I think black cowboy boots are the perfect fall/winter boot. They honestly can be worn with anything and they don’t ever go out of style. Yes, they have become more trendy thanks to Instagram influencers over the past couple years, but you’ll see me rocking cowboy boots until I am an old lady with gray hair and missing teeth. They are a timeless staple and therefore a great investment.

Boots (similar) | Pants | Shirt (vintage)

On to another simple (but essential) boot, the Chelsea boot. These are last year’s from Madewell and they are just a good boot all around. They have a good shape that tucks into pants and about a 1 1/2 inch heel so they are comfortable to walk/stand in for at least a few hours. They are almost identical to these but with a shorter heel. I’d say in general, Madewell makes quality affordable boots for everyday wear so if you are looking for a solid Chelsea boot, these are a great option.

I have yet to buy new boots for this year, so these are the three that I am drooling over right now.

1. Ezra Bootie | 2. Sofia Leather Ankle Boots | 3. Afelia Knee High Boot


Sweater | Dress | Boots

I’ve written about these boots a lot (and you may have spotted their platform clog counterparts in some previous fashion posts!) but MAN, they just don’t get old! These were my first pair of Charlotte Stone shoes and they kicked off a crippling addiction – I’m wearing shoes from this tiny female-founded brand almost every day at this point. These boots have a memory foam insole, super study construction, and they’re so comfortable (cause like, clogs are good for you, or so I’ve heard) pluuuuus they make me 6′ tall, which makes me feel super powerful and intimidating and cool. They’re fun and kind of funky and 70s-inspired and I just love them so much – saving up to add a new color to my collection this winter:)

T-Shirt | Jeans | Boots

Oh my gosh, MY NISOLOS. I wrote about these in the link up a week or two ago, but let me refresh your memory: if you’re in the market for a timeless, sustainable, last-forever leather boot, THIS IS IT. These are a few years old at this point and they’ve seen airports and international travel and all kinds of nightmarish winter weather conditions but they still look and feel brand new. Sometimes I also get kind of weird and self-conscious about boots and the way that they’re cut because they make my legs look kinda beefy or weird (to me, at least). So I am just JAZZED about the way these hit my ankles – there’s a little bit of space and they’re the perfect height (not too high, not too low). They’re the best for when you want to look kind of cool and put together (“who me? I just threw these on!”) while actually being super comfy and cozy. 100000/10!!

1. Loading Bootie | 2. Cromwell Cutout Western Boot | 3. Nordic Boots


Jeans | Shirt | Boots (similar)

I bought these black boots last year (they’re the same as Jess’s but in black!) because they were on an AWESOME sale (I’m crying they’re not made anymore but THESE are adorable and are soooo similar for $50 or these are also similar too and I’ve been eyeing them since Em wore them in this fashion post). I had been worried the boots were TOO pointy – and they were very tight when I first bought them because they didn’t have my size so I sized down but thank god they stretched (most leather boots do at least a little). These are 10/10 and everyone needs a pair of black boots.

Jeans | Shirt | Boots

Okay I know I just said everyone needs a pair of black boots and I personally believe everyone also needs a pair of snakeskin boots (THEY’RE A NEUTRAL!) I’ve had these for YEARS and they’ve yet to disappoint. I wear them pretty much every time I walk out of my house and they’re my go-to ‘going-out/dinner’ boot because they’re wildly comfortable and I can (and have) walked miles in them. Animal print boots are still big so get em while they’re hot!!!

1. Janna Over the Knee Boot | 2. Laguna Chelsea Boot | 3. Aslen Boot

That’s all from us, but because we are a curious and nosy, what are your favorite fall boots you can’t get rid of?? Drop em below and have a great Saturday. xx

Opener Image Credit: Photo by Veronica Crawford | From: Shopping My Closet For Fall & wearing Some (Ethically Made) Shoes That I Love

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Blundstones are really in but I can’t figure out how to style them. I’d love a EHD post about making Blundstones and other chunky Chelsea boots feline, polished, and winter style ready.

2 years ago

Second this suggestion. Please help us know how to wear blundstones and feel cool!

2 years ago

Good work, thanks for posting such nice work.

2 years ago

Keep getting served a Kochs brothers/Americans for Prosperity ad. Seems a bit off brand…

2 years ago

My lust for boots begins and ends with Nisolo Chelsea boots.
I can’t afford them. 😭 Boo hoo.

Allison C
2 years ago
Reply to  Rusty

I bought Madewell Chelsea boots a couple of years ago. They look exactly like Nisolo, and I love them. Perhaps you could find them on Ebay or other used sites? They were def less expensive (on sale).

2 years ago

Thanks for all the great fall boot suggestions and for your amazing blog in general – I always look forward to seeing what’s new on your site! I actually have a random paint question related to one of the photos above. In the lovely photo of Emily with the striped sweater leaning against a blue-gray window frame, I would LOVE to know that blue-gray paint color for an upcoming house painting job if anyone knows what that is. Thank you!!