10 Step Guide to Buying Riding Boots

You Pick Wednesday

Riding boots came into style for everyday wear a few years ago and seem to be here to stay!  And by riding boots I mean basically any knee-high boot with a slight heel, the occasional buckle, strap or button, a zipper and with a slightly more casual flare.   There are tons of riding boot options available and at this time of year you can probably get a good deal on a pair since stores are clearing out their fall and winter items to make way for sandals and swimsuits.  But don’t get me started on that rant.

Love these riding boots



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Anyway, due to the overwhelming number of options at multiple price points it can be difficult to narrow down a pair that will be both functional and flattering.  Sure, it’s easy to find ways to wear riding boots, but how do you know what criteria to consider when purchasing a pair?

Here ten suggestions you can use when looking for the perfect pair:

1.  Make sure the heel isn’t too high or chunky.  That will help them last through lots of seasons & styles.


Good                                                    Not Good


2. An almond or more pointed toe is better than a completely round toe as these shapes will help elongate your leg.  But don’t go too pointy! That’s a different kind of boot altogether.


Round                                       Almond                             Pointy


3.  They should hit you just above the widest part of your calf or 2-4 inches below your knee.  If they are too short they can make you look stumpy.


Same jeans, different boots


4. Real leather or faux leather is your choice depending on your feelings, but I will say that real leather ones will last for years and years and can be repaired and polished whereas faux leather will fall apart eventually and cannot be polished or repaired as easily. Also, I have found it difficult to buy faux leather brown riding boots that don’t look cheap.  But, if that’s not your priority then that’s okay, too.

5. Measure your calves!  And note the shaft circumference on the boots.  You don’t want them too tight or they’ll be uncomfortable and you’ll never be able to tuck pants into them.   Note:  the calf circumference noted on most online shoe stores is measured from a size 7 or 8.  The larger the shoe size typically the larger the calf width as well.  If you’re right on the edge of the stated calf circumference but your shoe size is larger than the one listed as the standard then I would suggest going ahead and ordering them.  Zappos has free return shipping so it’s easy to send back anything that doesn’t work.



6. I personally prefer to avoid anything that has a strap at the ankle as I think these can make you look sawed off at the ankles.  Some people don’t minds this, though.  Try on a pair that have an ankle strap and see how you feel when you look in the mirror.


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7. The fewer the embellishments the classier the boots look.  Simpler boots also tend to outlast trends.


Classy                                           Trendy


8.  Brown boots or black boots?  Personally, I wear my brown riding boots WAY more often than I wear my black riding boots.  If you’re okay with mixing brown and black you can always pair your brown boots with black pants.  But, really, it just comes down to personal preference.  Sometimes it’s easier to make black riding boots look classier for the office and brown more casual, but you can make outfits with either.


gray_blazer_black_turtleneck 006black-pants-red-sweater-gray-blazer (1)

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Similar outfits, different boots


9.  Let’s be honest about price.  Nice riding boots that last will not be cheap.  $100 seems to be the lowest price you can expect to pay for a new pair unless you find a great deal in the clearance section at DSW or have some killer coupons.  Both of my pairs cost me just under $100 and both are from DSW.  Leather riding boot can cost upwards of $700 to $1000 or more.  I certainly don’t think you have to spend that much, though!  $100 to $150 should get you a great pair that will last you season after season.

10.  Finally, think about your lifestyle and where you plan to wear them.  Are you mostly casual?  Then you might be able to spring for a pair with more flair.  Do you get tired of your clothes and shoes and want to replace them every season?  Then why not get something trendy.  But if you want to wear them to a more business casual office then you’ll probably have to stick with a more traditional pair.


Thoughts? What did I forget? Do you already own riding boots?  If you do, what did you take into consideration when you bought them? 



33 replies on “10 Step Guide to Buying Riding Boots

  1. kelsey

    great post! I have a really hard time finding boots that fit me correctly so when I do I snatch them up right away. I’ve tried buying a few online but the calves are too big, the ankle part is too slouchy, etc etc.

    I also am not a fan of the ankle strap!

    I have 2 pairs of black ones and I really need to find some brown ones!

  2. Kelly @ Running Kellometers

    I have a hard time finding black ones that I like that don’t look like motorcycle boots. For some reason, I think I mentally associate black riding boots with motorcycles. I guess that just means I haven’t found the right pair of boots! I have a cheap pair that I bought at Old Navy for about $30. I absolutely love them, but certain areas are starting to wear away. I think I will need to invest in a real pair soon!

    1. Melissa

      I feel the same way about my tall black boots! I feel too “rocker”/motorcycle and almost never wear them.

  3. Valerie

    FANTASTIC post- very informative and I never thought about the point of the toe elongating your legs! I LOVE my Aldo Candlish cognac boots…wear them literally almost every day! I specifically looked for boots that didn’t look exactly like rider boots. I love that they are gathered in the front, giving it more of a feminine flair and they have a full zip so they are easy to get on and off versus pulling them on! Definitely the most I ever paid for boots (retail at $140), but they are built to last and I get lots of wear out of them!

  4. Melissa

    Wearing my brown (cognac) riding boots today, actually! Paired with black tights and black/white sweater dress…so obviously I don’t mind pairing brown with black. I actually think it looks really chic.

    I commented on Kelly’s post above about my tall black boots. I have thought about replacing them but I’m getting so much wear out of the cognac ones I will probably save my $$!

    One thing for people that have larger calves (me!)…I find avoiding styles with a full length zipper helps immensely. I will occasionally try just to see if things have changed but a long zipper always leads to bunching around the ankles and a stuffed sausage look around the calf—NOT good! Styles that pull on or only have a small zipper (usually inner ankle) work and flatter 99% of the time.

  5. Bethany @ Accidental Intentions

    I’ve really wanted to get a pair of riding boots for awhile, but I have a hard time swallowing a $100+ price tag for shoes that I can’t run in 😉 It’s not *too* often that I have an occasion I feel calls for boots anyway, but in those rare occasions that do, I actually have a pair of hand-me-downs from my mom of all people that I wear. She wore the boots when she was in high school and/or college…so we’re talking like somewhere between 30 and 35 years ago. They’re a bit pinch-y in the feet (which is weird, since she wears a bigger shoe size than I do) and have this very weird black polish-esque thing going on on the INSIDE of the boot that ruins socks (so now I stick to black nylons if I’m wearing those boots), but they work when I need them to! And they cost me $0 🙂

  6. Kandi

    I’m not sure if the boots I own would be considered riding boots but I definitely get more wear out of my brown ones. My issue with all my shoes is that I tend to like brown shoes more than black (possibly because of the motorcycle/rocker look mentioned above) but my clothing for work tends to be more black related. I’m not comfortable yet wearing brown with black (although the dress I mentioned in a different comment is navy but everyone apparently thinks it is black and I wear that with my brown boots so…). I’ve been surprised how often I wear my brown boots. Probably because I finally have skinny jeans and boots with wide enough calves to work with them!

  7. Emily

    The wide calf size option was a big deal for me. I struggled for such a long time to find riding boots that actually fit my calves. For several years I always struggled mightily to zip my boots up to the point where I worried about breaking the zipper. Then I could only wear my boots with skirts, since they were way too tight to tuck my pants into them. I’d also have nice zipper-marks on my legs at the end of the day afterwards. Call them compression boots, perhaps?

    1. Erin @ Loop Looks Post author

      I’m right on the cusp of needing wide calf boots. If the leather can stretch a bit I can usually get away with non-wide-width size. But I do typically have marks on my legs when I take my boots off!

  8. Mica

    Yay! I feel like this post was written for me. It’s really overwhelming to look at the huge selection of riding boots (and boots in general), so I’m happy to have a good how-to guide of things to avoid and things to look for while shopping.

    1. Erin @ Loop Looks Post author

      You’ll definitely have more choices in stores if you wait until next winter. It’s so frustrating how stores ditch their winter stuff when it’s still winter!

  9. kilax

    Great tips! Of course, I don’t need them since you do all my boot shopping.

    It is frustrating that the faux ones do not last as long. But, I guess $70 a season is not that bad? LOL. That reminds me, I need to throw out last year’s 😉

      1. kilax

        Yeah, they fit nicely and look good. They only problem is that there is not much support and my foot hurts today after wearing them yesterday 😉

  10. Katie of Alaskan Weredork

    I’ve bought both the cheaper pleather boots and the real leather and I’ve been so much happier with the real leather ones, they last so much longer! As a side note, real riding boots can usually be purposed for about $200-400 if someone really likes the original look of riding boots, they are little bit cheaper than some of the designer boots.(Ariat, Dover Saddlery or Stateline Tack and they all offer small, regular and large calf sizes.) Steve Madden and Vince Camuto both do gorgeous real leather boots which are really comfortable and usually under $200. (I saw them on sale for $80 last year on pipperlime.com, those end of season sales are killer.)

    I think you really covered everything, that was smart mentioning the toe shapes, those can really date a pair of shoes and ugh, square toes! (I’ve seen some many pretty boots at the thrift stores that were great aside from having square toes.)

    1. Erin @ Loop Looks Post author

      Excellent points about getting “real” riding boots! I’m glad you weighed in since you definitely have the scoop on all things riding-related. And thrift-store related, too!

  11. Anne

    Thanks for the guide! Would you consider buckles as an embellishment that’s a short-lived trend? I’m on the hunt for some long-lasting boots, and while I like the appearance of buckles, I don’t want to make a purchase I’ll later regret.

    1. Erin @ Loop Looks Post author

      Excellent question! I think one buckle on the top or near the ankle wouldn’t be too trendy. I think the key is making sure the toe isn’t too square and the heel isn’t too high. Those are the things that tend to date boots the most.

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