Cold Weather

Riding Boots

It’s seriously getting close to riding boot season!!! Oh, I’m excited. Even though we’ve had some chilly days (mostly just chilly mornings) here in Manhattan, I really can’t wear boots until it’s “officially” fall– I think it’s more of a mental thing more than anything. And that day is just a few days away! (September 22 to be precise.)
Growing up in Florida, boots were really never necessary. Obviously I loved the way they looked in those back-to-school catalogs, but they were completely unnecessary. I wore Jack Rogers nearly year round throughout high school… maybe the occasional ballet flat. (Wait, actually… I only wore closed toed shoes when we had to for Chemistry. HA.)
Anyway, moving to DC for school was so amazing wardrobe-wise. Corduroys? YAY! Coats? YAY! Sweaters? YAY!
Riding Boots? YAY x 1000!
The one thing about riding boots is that they tend to be more expensive than most shoes, but if you buy the right pair and take (decent) care of them they should last a while. I got a pair of brown Tory Burch riding boots the fall of my freshman year, and they are still going strong. I’ve had them resoled a couple of times (Georgetown cobblestones are shoe killers), but that was totally worth it.
From Top to Bottom:
I love that you can really go for all kinds of shades. From light tan all the way across the spectrum to black.
This was a picture I took for College Fashionista and I’m still in love with it. Both girls (they’re sisters!) are wearing Madewell boots!
When are you officially pulling out your riding boots? What do you wear them with? What’s your favorite brand?

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That is such a flattering picture o you, Carly! I've had a pair of riding boots from dELiA*s for 3 years and they're still in almost perfect condition! One o the best (and cheapest) buys I've made!


I just brought mine back to school with me after my trip home this weekend, but have yet to wear them – I tend to wait until it's at least in the 50s before I break them out. The pairs I have right now are Cole Haan and Frye!

Erin Kerr

I just bought the Aldo pair you have featured this Sunday! I have skinny ankles and muscular calves, and even when I wear jeans they fit me! I had purchased the Melissa Button by Frye a few weeks ago, but returned them as they just weren't going to work. Luckily the Aldo 'Lavierdene' is so pretty and so much cheaper compared to Frye's. Of all the boots I've seen in the past few years, they are by far the prettiest I've seen–such a rich colour. I can't wait to wear them next week!

The Modern Prepster

Carly you look so pretty in that picture!! I have Arturo Chang brown ones that are in good shape but they are a tenny bit pointy in the toe so I'm begging for new ones! I'me going to wait until maybe October or late September, when it REALLY gets chilly! xxx

Ginelle Calotes

I have the Tory Burch Nadine in Black as well. They fit perfectly on my skinny calves and look so chic with just black leggings or jeans! Confession: I have the Merona Riding Boots in Cognac from Target (it was one of those Target trips where you go in for a gallon of milk and end up with a complete new wardrobe!). I ABSOLUTELY love them. I have very skinny calves (usually a 12'' boot shaft circumference is the ideal for me) but because the very top of the boot shaft angles down (like in your picture) it creates the illusion that these boots were made for me.

First time commenting! I love your blog!!! I am living vicariously through you and your life in the Big Apple 🙂


Are you sure the girl in the photo on the right is wearing Madewell boots? They look exactly like my Frye Melissa Button boots! Love your TB boots.


I love the look of riding boots but I haven't bought any yet. They're definitely expensive. I'm considering buying the Target ones but $75 is still expensive!


Maia Price

I have huge calves from dancing my whole life and I need to find some riding boots that are shorter (for my petite frame) and wider (for my monster calves) These are so cute, though!



I've been looking for a great pair for a while! I don't like the mustard brown color and in the style that I want that's the only color I find! I also need them for fairly inexpensive, because I can't make myself buy $160+ pair of shoes! Even though I know they'll last a while… sigh…

carelessly graceful


It usually takes me a while to pull out the boots at school because I go to school in South Carolina. 🙁 But when I'm home in New England, I love wearing my boots in the fall! I have a pair of dark brown boots with a small heel and I love wearing them with my skinny jeans and a cozy sweater. Enjoy the fall weather up north! I miss it!


I'm excited to invest in a pair of riding boots since I'm finally moving to a cold place! I'm also from Florida and just as guilty of only wearing close toed shoes for chemistry when it was absolutely required haha!

Hannah Ethridge

I'm definitely excited to be wearing my cowboy boots all throughout this fall and winter…and I'm definitely excited about fall being really close because it's my favorite time of year and it's three days before my birthday (Sept. 25). I really hope to get a pair of riding boots too this year 🙂 And Carly, I love that picture of you!


Carly! I noticed a spelling error in your E-I-C bio in the mag on page 3. "Always" is spelled incorrectly. Wanted to point out the typo in case you want to have it fixed. Cheers.


I'm the same way about boots- I absolutely cannot break them out until fall officially starts. Luckily, my cross country team decided that our spirit for our meet tomorrow would be "cowgirl". Its just the PERFECT excuse to wear my brand new riding boots a bit early!!

Leah Budke

I live in Belgium so I can wear boots almost year-round. It rains so often in the summer and rarely exceeds 75 degrees. Fall is definitely my favorite season, though. I've been out shopping around looking for a new pair of boots for this fall, but haven't quite decided on the perfect pair. 🙂 Also looking for a new coat and yours is really adorable!


Well, the fall weather in Michigan might be staying so I might be pulling them out when it stays steady in the 50's. I love to pair my boots with leggings and a long cardigan or thick sweater with either a cami or a shirt with a scarf. I always pair them with my skinnies and a blazer. i don't really have a favorite brand when it comes to getting riding boots but I've always loved the Vince Camuto riding boots and Steve Madden. Those Gabriella Rocha look so similar to my Steve Madden boots. Also It's great to shop for riding boots in the summer because they are on sale!!! my sister got some leather boots from Sears for 30 bucks! Her boots always get compliments ( a bit jealous of her for that!)



Beautiful! Riding boots are one of the classiest trends in ages…I hope it lasts for a while longer. Last night I went out to eat at a Greek place in Harrisonburg, VA where the JMU students often hang out, and saw several pairs. The season has officially arrived! Love how you pair yours with the pink peacoat and jeans too. 🙂

Rachel Bristow

I am thrilled I get more use out of my REAL riding boots now! I used to get made fun of for wearing riding clothes and now I walk into a store and people ask me where I got my clothes… it's so weird for me! I spent a good chunk of change on my boots a few years back and they've been perfect for everything because they're actually made to be haha.


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Alice Hicky

It’s good to see these type of boots are available for women who can’t wear real boots (knee high with heel). So much better than the now out-of-fashion ankle booties. They look great on you!