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A Few Of The Boots, Oxfords, And Clogs I’ll Wear To Death This Fall…

As someone who likes to be on the more modest side of foot show and tells (few people want to see my bunion and short wide toes – ALL HEREDITARY, MY FRIENDS), I get very excited when it’s not so hot outside and I can don a cute (full coverage) shoe. So today I have a few of my favorites to show you – no tall boots yet, that’s coming later. But good day-to-day staples for most fall occasions.

The Janeen Platform Mule – Madewell

Blouse | Jeans (similar) | Mules

If you’ve followed closely you’ve seen me wear my Rachel Comey mules for almost five years (they are still available and just so good). Well, these are a wildly more affordable version that I love. AND good news, they are a lot easier to walk in (the Comey’s are still comfortable, but they are at least 2″ taller so less easy to walk in). These are way more “every day” and I could easily wear them all day. Also not shown here are my Nisolos that I had to reorder because my dog ate one of them – but they are EXCELLENT. They are light nude and therefore very flattering and elongating (and so comfortable – I opt for them every time I want the height of a heel but know I’m going to walk a lot).

Judgement Bootie – Bed Stu


Admittedly, I am NOT selling those in this shot/outfit. I wanted to just wear the same jeans and top. But I was so excited to order these boots. Now sadly I ordered my typical size (7) and they were definitely too small so I had to return them. Then I realized that I truly don’t need another pair of splurgey boots so I didn’t reorder. But point is – the style of this pair is so cute.

They remind me of Brian’s Redwing boots that he wears every chance he can. I love this mid-heel, how tight the boots get at the ankle, and of course, how you don’t really have to lace them and can use the zipper. Such a good patina on the leather, too. Anyway, I hope I don’t regret returning them but def size up. These would also be very cute with socks, longer shorts, and a fleece – more of the sporty/hipster/hiker vibe.

The Rain Boots – Everlane

Rain Boots

I have no idea what I’m doing with my legs in that first shot – I i guess trying to show you how they look from the side?? These are GREAT, especially if you want rain boots that aren’t big old wellies (which I love, but less around-town friendly). I wouldn’t say these are great office shoes, but great for errand running, super comfortable, and obviously very cute.

Women’s Caribou™ x Boot Chelsea – Sorel

Chunky Chelsea Boot

Y’all, THESE ARE IT FOR ME. I LOVE these and have worn them so much already. They have that lug-sole look, but it’s rubber and not very heavy. They are Sorels (a brand I love so much) with a rubber base and waterproof leather on top. they look so cute with socks/shorts and tucked up into jeans. They are so comfortable, cute, and waterproof (so I can wear them around in the rain and mud and can just hose off). You’ll see me wearing these a lot this fall/winter.

The Dimes Kitten-Heel Boot – Madewell

Kitten Heel Boot

These are my other favorites and I’ve already worn them three times (and that’s a lot considering it’s still summer and I rarely leave the house). They are just really flattering and look so classy, but so simple. That little kitten heel is so cute.

I like wearing these with slouchier pants (think cargo or joggers), you know to comply with the “wrong shoe theory” (which I actually really like).

Classic Chelsea Boot – Nisolo

Classic Chelsea Boot

I’ve had these forever and I appreciate that Buttercup has left them intact. They are just so good, comfortable, flattering, in such a pretty rich color, and classic. (They also make a water-resistant version that’s just as beautiful, FYI.)

The Modern Loafer – Everlane


These loafers are definitely on the less exciting side, but I’ve found myself wearing them a lot for shopping, errand running (or work if I had an office, obviously). They are really comfortable and slimming.

I, of course, found WAY more on the internet that I loved while I was shopping, but sincerely trying to not buy too many that I don’t need. So instead I just rounded up some other of my favorites. I do wish I had styled some of these for you with the right outfit because context changes the style so much but these are all just good, classic, timeless, comfortable, and guaranteed to look good with most outfits (IMHO). Happy fall to all our feet!!

*Photos by Kaitlin Green

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Michelle Taylor
10 months ago

Love all the shoes, but where are your jeans from??!!

10 months ago

I have the same question! They are the perfect wash and leg style!
I was actually going to comment that a round up focused on what style jeans to wear this fall would be so helpful. I need to buy some new jeans and have no idea what to get. I’m petite (5’2″) with a more athletic build, and straight leg jeans that are flattering are so difficult to find. The JCrew vintage slim straight leg jeans almost fit like skinny jeans. Any ideas? I love Madewell but every time I try to buy something online, it’s sold out.

10 months ago
Reply to  Kate

LOFT makes really nice jeans for petite women. I am 5’1, slim built and I love their girlfriend style which are straight-legged and looser in the hips. LOFT often has sales so you can easily get a $90 pair of jeans for around half. I also really like DL 1961 jeans but I only buy them on eBay because they are way too expensive to buy at full price.

10 months ago

I came here to ask the same question!

10 months ago


10 months ago

Hey friends, the Nisolo Chelsea boot link is sending to the kitten heel , just to let you know. And because on Saturday, we’re all lazy on searching ourselves. Plus, Caitlin wants accurate data, I just know it. Thanks for the daily content. And geez, what a backdrop that entry has become!

10 months ago
Reply to  Jen

you’ve got my number!!! ha. thank you for flagging. all fixed for my fellow chelsea boot lovers!

🥰 Rusty
10 months ago

Those Judgement Booties are SO CUTE! They look really well made, too (straight up reminded me of Brian’s boots before you said it!).
Kitten heels are way cute, but NOT comfortable if you’re like, actually walking or even standing.
Those loafers are making me drool!! Cute AND comfy.
Wrong link to the Chelsea boot!! I’ve been lusting after them for sooooooo long – simply beyond my range now I’m free from abuse, but effectively poor.😕 Rather be free thpugh!😋

10 months ago

The bench and pillow combo is the star of this post!

10 months ago

Thank you for this!! I’ve been waiting for this line up. I agree with the above commenter who asked for a follow up post…I have such a hard time figuring out which cuts of pants work best with each type of boot. I need a cheat sheet!

10 months ago
Reply to  Elysha

Add a third to that request! How does one match shoes and pants?! Feel like at this age I should have figured that out, but alas I need EHD help!

10 months ago

Just jumping in to say— love Sorel, my all time favorite— and to mention that my favorite California designer, Lesley Evers, just opened her first store outside of the Bay Area— in Portland, on Alberta Ave. Her clothes are so fun and colorful and comfortable; check out the shop or her website!

10 months ago

Not sure why my comment is not getting through so I will ask again. Did you get those Sorel boots stretched, Emily? I ordered them after seeing your post about them but couldn’t even get my [very slim[ foot through the shaft. The elastic didn’t budge at all. I wonder if I got a bad pair or if there’s a secret to getting them on?

10 months ago
Reply to  Emma

ahh sorry must be a prob on our backend – can’t see any other pending comments! this one got through, though 🙂