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My Ultimate List of Tried And True Fall Shoes (That I Wear Season After Season)


I’m on a big ‘only buy what I need’ personal campaign over here, with some exceptions here and there of course (I MIGHT be shooting our first original photography fashion post next week – I miss them). So instead of me buying new fall shoes, I realized that I have a ton that I LOVE from seasons past that are still available. Welcome to my “review and recommendation” post with a big linkup of all the ones that I love and would buy if I needed new fall shoes at the end. Today we are talking boots, clogs, and mules – the fall shoe collective trio that is basically my favorite.

My Favorite Boots:

Leonore Faux Fur Lined Chelsea Boot

photo by veronica crawford | from: my new insanely comfortable “mom-friendly” weekend wardrobe

These were the first Dr. Martens in my entire life. And if you want to sound like a total tool you can also call them Doctor Martens like me. The sheer pronunciation shift from Doc to Doctor ignites a giggle that says ‘you are old and weird’ but in a really endearing way. I LOVE THEM. They have the classic chunk and clunk of the brand but in a warm leather and simple profile. And the ankles tuck so well into pants. I just started wearing them again this season and want to recommend them hard.

Cloudy Waterproof Chelsea Rain Boot

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

I still have these and have worn them repeatedly during damper days. They are kinda stiff which bothered me at first, but they are affordable and keep their shape (and yes, loosen up). I’m a fan.

Hudson Waterproof Boot

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

Admittedly when we shot this last year this is NOT the outfit that sells these boots. But these boots are WONDERFUL winter boots. They are waterproof, warm, can be trudged through the snow and there is no chance of anything getting into them because they are so high. I know they might not be for everyone’s lifestyle but for us in the snow with the hiking in our back yard, these boots are awesome.

Classic Chelsea Boot

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

These are still my go-to’s for daytime comfort that are still strangely flattering. Because of how they are designed, they slim my wider feet and tuck up nicely into all my jeans. They are so comfortable (and sustainable).

The Cowboy Boot

photo by veronica crawford | from: why i am suddenly dressing like a toddler

Admittedly I’m not really selling these boots in this shot, but those cowboy boots are still my favorite when I want to add a huge dose of “I care”. They are splurge-y, but I have worn them a ton over the last two years and the pony doesn’t get dirty. I like them more with socks and pants.

The Regan Boot

photo by veronica crawford | from: six fall sweaters i’m loving (+ how to wear them)

These are my classic Chelsea boots with a heel. They are so comfortable, tuck into pants easily, and work with anything.

Pikolinos® Vicar Boots

photo by veronica crawford | from: a fashion review: new clothing on my body and how I like them (or not)

That photo on the left isn’t my favorite pose ever but these boots remain #1 in rotation. It’s hard to explain why. They look like normal boots but they are so lightweight and comfortable that I can’t help but opt for them almost every day. Two of my friends have bought them after wearing them. They are just strangely cute and comfortable with no cumbersome heel or constricting toe.

My Favorite Clogs:

Amber Orchard Clog

photo by veronica crawford | from: my favorite current clogs – a review

UGH. I can’t wait to have an occasion to wear these again, but I still LOVE these clogs. They are so comfortable and cute and you know I love a nude shoe with a heel.

Belems Clog

photo by veronica crawford | from: my favorite current clogs – a review

I didn’t end up keeping the blue ones in this photo, but I did keep the snakeskin ones that I can’t wait to wear more consistently (with socks and tights). But looking at that photo I’m wishing I kept both pairs.

The Ayanna Clog

photo by veronica crawford | from: my casual, cool spring weekend wardrobe

These Madewell clogs are so cute, classic, and affordable. Oh wait, and very comfortable as all clogs should be. They are the chunkier version of the Rachel Comey’s that I’ve been obsessed with forever.

My Favorite Mules:

Mariella Mule

photo by veronica crawford | from: why i am suddenly dressing like a toddler

I used to wear these mules all day every day. They have the perfect short heel and are so comfortable. Up in the mountains, I get too much dirt and leaves in them in the woods, but as soon as we start going to public places these are my go-to’s.

Paloma Mule

photo by veronica crawford | from: 5 fun and unexpected summer office outfits

The taller version of this mule is a classic that is convincing me right now that I need to make occasions to wear real shoes. My Vans and sneakers are getting all the use these days, but maybe soon Brian and I will book a safe outdoor dinner date and maybe I can wear real shoes. If my feet can handle it …

Now if I WERE in the market, here are the 2020 fall shoes I am loving right now:

1. Sam Edelman Laguna Chelsea Boots | 2. Super Platform Loafers | 3. The Carlotta Tall Boot | 4. Frye Campus 14L Boots | 5. Alma Clogs| 6. The Modern Utility Chelsea Boot | 7. Lauryn Mule in Dandelion | 8. The Frances Loafer | 9. Dolce Vita Sammey Ankle Boots | 10. The Alex Heeled Loafer in Leather and Suede | 11. The Glove Boot in ReKnit | 12. The Chelsea Rain Boot | 13. Cecelia New York Theo Hiker Boots | 14. Frye Harness 12R Boots | 15. Lauryn Boot in Midnight | 16. Culver City Clogs | 17. The Harper Mule | 18. Suede Platform Chelsea Boots

Alright, that is all for today. Happy Saturday and happy shopping! xx

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

Fin Mark


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Deborah N Flanagan

I’ve got the Hudson boots and they are fabulous. So warm. Truly waterproof.

I just bought your Styled book and quickly ordered one for my daughter. Great inspiration.

ah, thank you!! we are working hard on book #2. Coming in October (of next year). xx


I would love to wear clogs. Unfortunately I have a size 9.5 foot and every pair of clogs I put on looks like I’m auditioning for the circus. Anyone out there (with similarly large feet) found a brand of clogs that doesn’t make you look like you’re wearing clown shoes?


I have size 10 feet find that clogs look cute but are incredibly uncomfortable for me- maybe it’s because I have low arches but the inflexible sole is killer.


Same size 9.5 here — I have these Lotta from Stockholm clogs which are not as cute as what Emily has here, but are comfortable, v affordable, and not clown-ish (IMO) :


9.5 and I have a peeptoe like swedish hasbeen and I actually feel, it makes my feet look smaller .. (not sur about the name of my model .. )


9.5 here and I agree that the peeptoe helps clogs not look so big.

Colleen Kyle

Pikolinos are great shoes; thanks for the reminder to check out their line! And since you are heading back to Oregon I want to plug Sorel–a great brand with stylish weather-proof boots, booties and shoes.

I love Sorel, too 🙂 I have a pair that I forgot to include up there. xx


You’ve inspired me to actually wear my cute boots for my outdoor, socially-distant dinner tonight!

This is the kind of recommendation post I really like, where you tell us the stuff you still love after you’ve had it a while


I’ve had to discard several pairs of shoes and booties that no longer work for my feet (combo of bone spurs and bunion… fun times!). So I’ve been looking for replacements. I’ve ordered and rejected a bunch of booties and finally found one that works. I wore it in my building walking several miles before I decided it was really for me. So I bought it in leopard print and now ordered it in black.
I’m done for the year. I’ll waterproof them before wearing outside as I do with all my shoes.


you are a footwear queen!

ha! thank you. my bunion gets worse every year so open toe model I am not. xx

I’d love to see you try on a pair of Timberlands. They are the most comfortable boots I have ever owned in my whole life and I swear that they are cute with cropped wide-legged jeans and a cropped top.

OOh i’ve never tried …. i’ll check out. xx


Is it still in style to wear knee high boots with jeans? Genuine question, would love everyone’s thoughts…


Is anything in style any more? If you like it and it looks nice why not?

I still wear jeans tucked into higher boots but it only seems to work for me with really tight jeans, otherwise the knees of my jeans go weird and bunchy. I also like to wear my mid calf boots with jeans tucked in but with thicker chunky socks.

Lora Kelberg

Yes of course.Plus wear what makes you happy snd feel good.You always look best when you feel happy in what you are wearing.It shows on your face and attitude.I am not suggesting that you don’t change things up but if you wear clothes that don’t feel good to you it will take away from everything else.Enjoy what feels comfortable to you and own it.


Ohhh I’ve been listing after the nisolo’s for a while now!!!!! Trying to decide between the black on black, brown, end black in brown! Oh, decisions. So glad to hear they’re comfortable.


Consider me Em-fluenced, I just ordered the Dr. Martens and hope they are as cute in person as you make them look! Since I don’t have anywhere to get dressed up for these days, I’m investing in stylish casual-friendly pieces to take the place of my abandoned high heels.


I’m confused: are you implying that saying “Doctor” instead of “Doc” makes you old? I’d say it makes you young. We were wearing these in the 1980s. They are a super comfortable, timeless shoe.

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