Fashion Advice: Riding Boots? Yea or Nay

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Dear Budget Fashionista,

I’m thinking about investing in a pair of knee-high brown boots, hopefully for less than $200. I’m in love with the current riding boot style, but I’m worried about their fashion staying power. How long do you think the low-heeled riding boots will be in? Are they a safe investment?

Answer: The low heeled riding boots might not be “in” style, but these classic boot style never really go “out” of style.  The key is to look for boots that are rather “trendless”- choose leather rather than suede (which isn’t as durable), keep the embellishments to a minimum (i.e. no metal horse bits), and waterproof them at least once a month.

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  • giselle

    ….and 5 years later, they are, deservedly, just as sought after!

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  • Samantha

    Go for it. I just bought some from Forever 21 for just $40!!! For $40 who cares if they go out of style in a few weeks!

  • Carmen Bush

    I’m not sure it’s important or not, but the circumference on the riding boots (size 10) seem too wide for my calf after I have skinny jeans tucked in. They are a little spacious. Fashion faux pas?

  • Jane

    Can someone tell me the brand/style/model of the boots the writer chose to pair with this article? I’d love to go try a pair(I’m in Los Angeles) Finding nice boots with quality leather and waterproof and comfort= challenging.

  • Symphanique

    The new riding boot stlye is sooo the look!! I saw a pair of black patent leather ones..they were so HOT!! need 2 get me a pair!

  • <a href="">Wide Boots<

    Very interesting

  • D

    I have a great pair of “real” black riding boots that I also sometimes wear with skirts & jeans. The difference is the zipper is never on the inside of the calf on the real ones (if they have a zipper at all).

    I think they always look cool, year after year. They can look military or country-casual.

    I’m planning on buying a brown pair of “fashion” boots though because I think they will be easier to get on and off.

  • Yeah they never go out of style.  I’ve had my favorite pair for 7 years now, and they still look like new (granted, I don’t wear them on a day-to-day basis, but still).

  • hf

    Riding boots seem to be one of those revolving trends that comes around every few years (along with riding pants and jhodpurs), but there are many people that are faithful to the look year-after-year. I’d say your safe getting them; but I’d get a pair that’s more classic than trendy for some longevity. And, I keep seeing flat boots everywhere, especially over-the-knee … haven’t decided how I feel about those yet.

  • I have a pair of Frye boots (Engineer), and although they might not be trendy, they certainly will not go out of style. I would just stay away from cowgirl boots (decorative stitching and pointed toe), and keep it as simple as possible.

  • Meshia

    Oh yeah, and Marshall’s had a great pair for $48.00 last week in a dark brown and a lighter brown color so be sure to check those stores for good name brands at low prices all you fabolous budget fashionistas!

  • Meshia

    I bought a pair of these boots last year and I loved loved loved them! Guess maybe I was ahead of the trend or something but they certainly will not go out of style! And to Eulalia, don’t worry about being petite. I too am petitie, (5ft, 2in) but I still wore them and I didn’t look too much like a runt with really short legs or anything. The key is to keep everything else short. Shirts should stop right above the top of the pants, definitely no tunics, you are sure to look like an oompa loompa!:-) Last fall I liked to wear it with long sleeve button up shirs that I belted with a skinny belt or cardigans that I belted and skinny blue jeans. Just keep it simple and oc course accessorise!

  • juliette

    I’ve been wearing these for the past 10 years (in different colors, though mostly black and brown) and as long as the heel and toe shapes are not extreme, you should be able to wear these forever.

  • eulalia

    I do love the riding boots, but as a somewhat petite person (five ft, 4 ins)I’m worried about how such high boots will look on my short legs. Anybody have any suggestions?

  • geri sculley

    i love the new riding boots look. i’m six feet tall and have large feet so i celebrate the fact that i can now buy low heeled, gorgeous boots. i’ve bought several pair this year and i don’t see them going out of style anytime soon. i’ve had a hard time finding boots because of my large size but have had very good luck at several websites. i’ve found some at, always a reliable source for generic boots and shoes in larger sizes, but i’ve really scored some exceptional finds at a site called i am awaiting delivery of a pair of low heeled, cuffed knee higs boots as i write this. i’m really thrilled with the fact that these boots will un-cuff and i can wear them as above the knee boots. this, at 6 ft tall, is something i’ve never been able to do.
    happy shopping.

  • I personally love my riding boots. I have a pair of black ones (Naturalizer’s Devon), and then a pair each of black and brown boots with a heel (Naturalizer’s Kiersten). I got them all last year and I wore them the whole winter long. I live in a warm climate so they are the perfect solution for me—-I rarely even have to wear tights with them. In any case, I highly recommend the Naturalizer line—-they come in both wide widths and extended calf. Their boots tend to run narrow, so if you have even a slightly wide foot, go for the wide width. I know you can get them at Piperlime, Endless, and, and I believe they are on sale now, too. With free shipping and returns at all three sites, it never hurts to try.

    I clean mine regularly and store them in one of the Container Store’s boot boxes.

  • christal

    I am not sure about the staying power of these but I am getting a pair.  I went shopping for some last Saturday but couldn’t pick one.