Fall Booties

Rainy Days

fall booties

one, two, three, four, five(out of stock), six, seven

As a follow up to my fall flats post from a few weeks ago, I thought I would share some of the booties I’m loving this fall! I wear the Dolce Vita Keiton booties all the dang time!

Thank goodness for stylish friends to show me the proper denim rolling height, and also the rule of wearing socks with booties. Apparently it’s either full sock or no sock, but you never want partial sock to show. I don’t know, I just follow the rules rather blindly.

I love a good knee high boot too, don’t get me wrong, but ankle booties are turning out to be pretty perfect for this time of year when it’s not really cold enough for full on boots but you still want to wear something more than just a flat.

Have you gotten any booties for this fall? I’m pretty set on my neutral/light taupe pair, and my black pair, but I wouldn’t put it past myself to pick up one more pair since I wear them so much!


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Melissa G says · 11.06.15

Well, bummer. Some of these are super cute. But, like the jeans, so expensive!!

Kate says · 11.06.15

I can usually find relatively inexpensive flats that last, but not comfortable boots or booties. Unfortunately the cheapest pair, from Old Navy, are out of stock!

Sydni says · 11.08.15

Target has some that look just like the last pair (seven) but are black! So cute. They have lots of other cute boots too!!

Jackie says · 11.08.15

I thought the same thing at first, but Kate is right. The only pair of comfortable booties I have found are always $100+. I found a pair of Lucky Brand booties at Dillard’s last week for $129, but decided to check out their online site before buying. I’m so glad I did because they had the exact ones I wanted for half off and no shipping costs!! Plus they offered an extra 20% off your first purchase. I was so thrilled to get a high quality pair for under $50. I know they still have that sale going on – I just ordered them last week. I wore them to work the other day and my feet didn’t hurt at all. I’m a teacher so I was on my feet all day and didn’t take them off until 5pm.

Jess E says · 11.06.15

I have a beautiful pair of black booties from Nine West that I want to wear with my skinny jeans. But, I need a cuffing tutorial! haha. My skinny jeans are perfect with flats, but when I put on the booties, they definitely need cuffed. help!

Chelsey says · 11.06.15

Please share the proper jean rolling height. I too, am late to the bootie party and I think I’m doing it wrong (I for sure am).

And while we’re at it, what height should your “full sock showing” be? Mid-ankle? Mid-calf?

Jamie says · 11.06.15

YES!! PLEASE share a cuffing/bootie tutorial. I just got some Old Navy booties because i’m still on the fence about the whole thing (HATED the trend at first). I tried to put together some outfits this week and felt like a hot mess.

Leigh Ann says · 11.06.15

Oh my gosh yes. I’m a bit lost on cuffing, socks, no socks, etc.

Kacie M says · 11.06.15

I bought a pair of taupe booties last spring from Crown Vintage, and finally wore them last week… love! So comfy and adorable. I’m off to DSW on my lunch break today to buy some black booties to wear with shorter pants for the coming winter, but then to also have for when the weather is warmer again (ya know, in 5 months!). I have found that good boots are not cheap, but I’d rather have quality over quantity, and most last a long time with average wear.

Lauren Ford says · 11.06.15

Run, don’t walk, to your local Steinmart or Marshalls for great booties under $100! I was there ( Baton Rouge) last Saturday and they had miles of fabulous good brand boots and booties at ridiculously great prices.

Laura jones says · 11.06.15

I’ve been searching for an affordable pair of black booties! I have a tan/brown combo like #7 (but in suede) and want a pair of black ones….can’t decide between leather or suede again (leaning suede)

phoebe ray says · 11.06.15

do you have a problem with the suede on your dolce vitas getting dirty?

Adrienne says · 11.06.15

Well….now I have to go shopping!

Sasha says · 11.06.15

How do you find the quality of Dolce Vita? I had some booties from them that I loved, but the heels wore down really quickly. 🙁

Teresa says · 11.06.15

Ok my 2 cents. I agree that booties are good for that transitional weather but I think knee boots make everything seem more,,,um polished, refined. Plus as a girl with a apple-y hourglass-ish shape with thinner thighs but mire muscular calves I find that a knee boot balances better. I starting to prefer my skinny boyfriends with the angle booties ( hidden socks/sloppy cuff).
In the shopping side I have a pair of Sam Edelmans from nordys that I have been wearing for 2 years and feel great. I have to highly recommend Clarks just because the comfort level and quality is just incomparable to anything I’ve worn. And I ain’t no grandma, but when you are running after kids and dogs you don’t want to curse your shoes. Clarks have upped their style game by miles.

Missy Robinson says · 11.06.15

When target had their Cartwheel 40% off last week, I purchased two pair of booties! I am so excited … navy blue and neutral leather. They are fabulous (Sam & Libby) and only $45 full price.

Melissa G says · 11.07.15

Now that’s my kind of price!!

Jessica says · 11.06.15

I’ve been intimidated by booties because the jean cuffing protocol seemed complicated. Now you tell me there are sock rules too? Arghh! I think I’m going to try nonetheless.

(The full sock showing vs. no sock, made me think of how people used to say “it’s snowing” to alert you that your slip was showing. Does anyone even wear slips anymore? Does anyone still say that?)

Nikki says · 11.06.15

I still wear slips!! And if you ask me, more women need to! Lol. I don’t know how some women wear dresses with no panty lines showing. Even if I wear a thong you can see the lines at my hips if my dress gets pulled up tight (like walking or in the wind…). I do NOT do panty lines, so a slip it is! I’ve even been known to wear Spanx with a slip over that to hide the seam lines…lol

Sara w says · 11.06.15

I bought the greige side zip toms wedge booties last fall and wear them much more than I thought I would. They’re a great in-between dress and casual

Alyssa says · 11.06.15

I love the blush ones! I have to admit, I have a couple pairs of booties, but I’m much more of a regular just blow the knee boot kind of girl. I just haven’t figured out how to wear them correctly yet!

Alyssa | Glitter and Grey

Jill says · 11.06.15

Yes I DEFINITELY need the cuffing and socks/jean height tutorial as well!!! I just bought 2 cute pairs of booties but I cannot figure out what to do with my pants!

Jennifer says · 11.06.15

I have the hardest time with booties! I LOVE them but I have small ankles so they all look like they are 5 sizes too big! How do you find the perfect fit? i’m also a size 5 1/2 so I’m thinking I should just ship in kids because they are impossible to find.

Kirsten says · 11.06.15

Ooh, I’m loving the bootie look. I recently bought a Nine West suede grey pair from DSW, with discount and coupons (score!). I want to get a tan pair with a higher heel for more of a dress up look. I’m not sure on the cuffing thing either.
I love my knee boots, but I’m getting tired of that look, so I don’t wear them as often.

Melissa says · 11.06.15

I’m coveting #7 in taupe. Unfortunately I don’t have a hundred bucks to drop on shoes right now. Oh well. Goodwill, here I come! LOL

Dominique says · 11.06.15

All these booties are awesome! I love Fall specifically because I can bust out my boots! I got a new pair from my sister, 2 weeks ago, Frye makes them and they are super comfy!


Nicole says · 11.06.15

I just ordered these TOMS wedge booties and am anxiously awaiting their Tuesday arrival. Nothing but good reviews on comfort!


Melissa Klotz says · 11.11.15

What do you think of them? i bought them last year and I wish the sole was more curved upwards on the bottom instead of totally flat. Wedges that are flat on the bottom make me feel like I’m *clomp*ing around, they don’t have that natural bend like a flat shoe does to support how your foot moves. I too heard they were “so comfy,” so i was kind of disappointed. Another thing I look for in wedges is that they’re not too heavy. These aren’t light, but they’re luckily not in the too heavy range!

Andrea O says · 11.06.15

I have a few pairs but not sure how to do the cuff on jeans either. And I have seen pictures of them with a skirt and tights but not to sure about that look.

Could you please tell us what your friends said about rolling the jeans correctly?

You have the best blog!! You do an amazing job with it.

Jasmine says · 11.06.15

I second the Marshall’s/TJ Maxx suggestion… lots of options currently. I have these and have received lots of compliments:

A Little Dose of Makeup says · 11.06.15

I want all the booties!!! I will have to check out all of these!

Stephanie says · 11.06.15

Totally off subject and hopefully not weird, but I had to tell you about a dream I had last night! You asked me to babysit for you and you were gone for like an hour and when you returned, the house was already a complete mess! And you didn’t have 2 boys, but a boy and a girl! Crazy and weird!

Michelle says · 11.06.15

My new find for the fall is a grey pair of Issac Mizrahi Live! Leather & Suede ankle boots…:)

Dusti says · 11.06.15

I found some cute ones at Old Navy for $39! Unforunately, they’re not online. BUT, make sure to go up a size because I’m a usual 6.5 and bought a six, and now I want to cry every time i wear them!

Love that sock rule…never heard of it before but definitely good to know!

Fashion Over Matter says · 11.06.15

Great post! Loved the urban outfitters one!! I love nude shoes, just can’t get enough of them.

Lexie Robinson says · 11.06.15

I love booties! They are one of my favorite parts of the season. Thanks for sharing.

Breanna says · 11.06.15

I just bought a pair of Franco Sarto booties at TJMaxx…and I am obsessed.They are a gorgeous dark gray coloring. I LOVE them! I still haven’t ventured to wearing them with high socks…not sure if that’s my thing. But I am definitely an ankle boot convert!

McCall says · 11.06.15

Please share the knowledge of proper denim rolling height!!

Veronica says · 11.06.15

I’m late to the bootie party, too. I really didn’t like it at first, but I’m starting to see the light. I’m trying to figure out all the sock and cuffing rules. I came across these helpful links: http://advicefromatwentysomething.com/3-ways-wear-socks-booties/ http://advicefromatwentysomething.com/how-to-wear-booties-with-skinny-jeans/

Heidi K says · 11.06.15

Love those booties! I just got a pair of Toms charcoal wedge booties at nordys last week and they are comfy and can dress up or down! So far I’ve dressed them down b/c I’m running after my 2 littles! Love your blog!

Cathy B. says · 11.06.15

Thanks to all of you who requested the cuffing tutorial and information about socks or no socks! Yes….I definitely still wear slips, especially if my dress is very sheer. I try to avoid them as much as I can in the summer, as they add some extra heat.

Jennifer Peer says · 11.06.15

Booties are my favorite fall shoe! Good quality ones tend to be expensive, but I just got my first pair of real leather booties from Lucky Brand and I can honestly say they were completely worth it. Number 7 up there is calling my name…
I started my own blog a few months ago and it would mean so much if anyone has a few minutes to check it out and give feedback! http://www.jenniferpeer.com

Sandy says · 11.06.15

I got my first pr of booties last year in black and didn’t wear them a ton but I fell in LOVE with the number one pair you shared here and had a GREAT DSW coupon to use, so. I got the beige/taupe color and love them. I didn’t realize there was a cuffing trick though so I guess I’d better do some research or wait for you to share your tips/tricks?

Kristi says · 11.06.15

I bought some booties for the first time this fall, and I am loving them! I think I need another pair that has a lower heel though, so I am definitely going to keep my eye out for something like the Crown Vintage pair.

Kristi | Be Loverly

Evelina says · 11.06.15

The perfect denim roll is a skill with booties like this! I love your #7

Mary Kate says · 11.07.15

I’m all about booties now that it’s cooled off some! I love the number 7 ones!

Mary Kate

Lizzy says · 11.07.15

I just bought my first ankle boot from Clarks. They are amazing! So comfortable and look like they are worth more than I paid. They are having a 20% off sale right now. I could live and work in these all day. I had to ask the stylish saleswoman about the cuffing guidelines on pants haha. With the 20% off sale I ended up paying $120…worth every penny for comfort and quality.

Lauren says · 11.07.15

I grabbed these new pair of Toms Leather Booties and they have been perfect so far. I wear them a lot and they are super comfortable and the leather is such a beautiful color for fall.


Greer says · 11.08.15

I love these –> https://www.dansko.com/Womens/Footwear/Collections/Tivoli/Maria/Taupe%20Milled%20Nubuck/

I have them in taupe and absolutely love them. They are comfy and seem to go with nearly everything! They’re sold out, but will be replaced in the spring with these –>https://www.dansko.com/Womens/Footwear/Styles/Clogs/Markie/Markie%20Taupe%20Milled%20Nubuck

Allysia says · 11.09.15

I did not know the full sock/no sock thing, ha ha. Do your socks have to be a certain height for this to work? Apparently I need to do a bit of internet research!

sabin says · 11.09.15

I really love #6 – but your link doesn’t seem to work – i searched the nordstrom site and no luck on “cider bootie”. 🙁

Elizabeth says · 11.09.15

I’m a real hot mess when it comes to everything stylish…Kate, I think you should show us all of your bootie wearing techniques that you learned from your friends. I don’t even know what types of pants to wear or how to roll!

Mary says · 11.09.15

I just ordered a pair from Nordstrom (Jeffrey Campbell) and while they were cute, they hurt my feet and I twisted my ankle trying to wear them. So after sending them back, I stumbled upon the Dansko Maria style and ordered them. Boy, I just love them. They are about $169 like the previous pair. Very comfortable though and I know they’ll last forever!

Kristin S says · 11.09.15

I’m just scared. I’ve seen them on others for a few years and looked away knowing they would look silly on me. The ONLY small part of my body is my ankles (are my ankles?) and wrists. The thought of cutting off my leg at that point scares me.

I tried on a few pair at TJ Maxx last week and looked like the biggest wanna be poser. I think my body is just not made for them but they are so cute on others!

Kelli says · 11.09.15

Do you have to wear booties with skinny jeans? Skinny jeans don’t look good on me. I look better in slightly boot cut jeans. Obviously, I won’t be cuffing them. Does that mean I can’t wear booties? Please advise!!

Shannon says · 11.10.15

LOVE IT!!! Booties are pretty much a closet staple of mine! These are some great options!!!

Kayleigh Mydosh says · 11.12.15

Hi Kate and fans!

I love this blog and follow it regularly. Something about Kate is just so peaceful and her posts are so beautiful. I just started my own blog https://theminimalistjourneyblog.wordpress.com/ and would love if you could check it out or comment. It’s brand spanking new so I would love any and all advice!

XO Kayleigh

Tiffany says · 11.16.15

Any chance you can show us how you wear your jeans w/booties? I never know about socks/no socks, how high and wide to roll the jeans, etc. Maybe your sister can show us some photos of bootie dos and don’ts.

Stephanie @ ChalkSouthernToMe says · 11.17.15

I find myself wanting booties in every single color right now, the addiction is real! Loving your picks! Xo, Stephanie

Michelle says · 12.07.15

Ok FIRST – I am way out of my league here because I have never nor could I ever pay more than about $40 for any shoes or boots. SECOND – I love shorter boots …. but the kind you can still tuck your leggings into …. or booties that look kind of like work boots (only way I can describe them) so jeans go OVER them. I just can’t catch up. Not sure if I like this particular bootie trend …. maybe if I, too, knew the rule for cuffing/ socks/ no socks/ snowing?