Why Every Woman Needs A Pair of Classic Riding Boots This Winter

Happy #fashionwednesday, everyone! I am a sucker for shoes – who isn’t, amiright? – and own literally dozens and dozens of pairs. Personally – I’m a firm believer that you just can’t ever have enough toe tappers in your life. I’ve written several shoe guides over the years, but the one pair of shoe I just can’t stop gushing about is my tried and true, ride or die, dress it up dress it down classic riding boot. I hear them with dresses, jeans, black leggings, color pants..you name it and more than likely you can find me wearing it. If you haven’t bit the bullet on a good pair of riding boots yet – now is the time to do it. Winter shoes are on clearance and I got these babies for $11. YUP. ELEVEN DOLLARS. Excuse me while I skip away with practically highway robbery. Keep reading to find out why every woman needs a pair of classic riding boots this winter:

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

They are flattering on all leg shapes.

Some girls I know refused to wear tall boots because they had wider calves. That is utter nonsense – you just need the right size calf on your boot!! You can also choose the height so if you don’t like a certain part of your leg – I bet there is a boot to cover it. I prefer boots right at my knee or a little bit below. A dear friend of mine prefers mid-calf. Find the style that flatters you most.

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

They last for YEARS.

Honestly, the leather boots I had from high school last all the way up until last year – so more than 7 years. They were less than $100 from Dillard’s and should honestly get some kind of award because I was so rough on them. If you take good care of them, they should be a purchase you make once every decade or so. 

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

They never go out of style.

A pair of tall leather boots won’t ever go out of style. They are classic, like black pumps. You don’t have to worry about not being trendy or feeling embarrassed to wear them – which is awesome because those are the kind of staple pieces I live for in my closet. 

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

My 3-Step Guide To Buying The Perfect Pair

  1. Get the right heel. A heel that is too high or chunky will be uncomfortable and less versatile. Opt for a low heel that is seamless with the body of the boot for a relaxed fit and timeless style.
  2. Opt for the almond toe heels when you can. Pointy toe boots can cut off the circulation in your foot and round toe boots can tend to look younger rather than sophisticated. Almond is that perfect balance of class and comfort.
  3. Go faux. Faux leather has come a LONG way and it’s almost impossible to tell the difference now. I have been so impressed with the quality of my faux leather boots and bags, so if you can, go FAUX!


Why Every Woman Needs A Pair of Classic Riding Boots This Winter

I’m not sure if you noticed….but I LOVE riding boots. This is one of my go-to outfits because it’s flattering and hello layers in the winter and spring of Missouri. AND riding boots look notoriously adorable with jean jackets – my all time favorite layering piece. Let’s be honest – I have struggled letting go of the early 2000s. Those were the days. ๐Ÿ˜‰

Why Every Woman Needs A Pair of Classic Riding Boots This Winter

Did you like this outfit? Did these tips convince to run – not walk – to your nearest target to get your OWN pair of $11 riding boots? Let me know in the comments below

About The Author

Taylor Mobley


  1. Karli Ellis | 31st Jan 18

    You totally convinced me! These are so cute and I love the color! Thanks for sharing! xoxo
    Everyday Ellis

  2. Leslie@Peaches&Willow | 31st Jan 18

    My husband and I found a great bargain place around us that sells boots for 60% off so we’ve been going back every week or two to see what they have in stock. He’s found two new pair and I’ve found one but we love them so so much. He wears his daily!

    I do love the tip about the almond toe though. I’ve never really given it much thought but I know I don’t like boots that are too pointy. I’m going to be on the hunt for a pair with almond shaped toes now! I love the ones you have one. What a steal!!!

    • Taylor Mobley | 31st Jan 18

      OMG THAT IS AMAZING. And right – I am ALL about a bargain!

  3. Holly | 31st Jan 18

    I am absolutely in love with the color of these boots. They are absolutely fabulous.

    xoxox Holly – collegewanderlust.com

    • Taylor Mobley | 31st Jan 18

      RIgHT? Target’s got them right now ๐Ÿ˜‰ ScorE for clearance shopping!

  4. Ashley Stephenson | 31st Jan 18

    I love my riding boots! I have two pairs in different shades of brown and wear them constantly throughout the fall and winter!

  5. Erica @ Coming Up Roses | 31st Jan 18

    I mean OK hi yeah you’re the cutest ever. Also I LOOOOOVELOVELOVE your boots. Can I have them plz? Kthanx.

    • Taylor Mobley | 31st Jan 18

      Yeah pretty sure we wear the same shoe size soooooo.

  6. sara | 31st Jan 18

    Those books are gorgeous! I have such fat legs that by the time I find a wide calf boot that isn’t ugly as sin, there’s only ONE pair of pants it works with because my pants make it too tight so it feels like such a waste of time. But man I love them on everyone else.

    • Taylor Mobley | 31st Jan 18

      Ok so for wide calves have you tried adjustable boot legs as opposed to straight boot legs?? They were a game changer!!!

  7. Holly | 31st Jan 18

    I LOVE riding boots! They’re so stylish, and I completely agree…they go with practically anything! xx

  8. Helen | 31st Jan 18

    Those boots are fantastic! Seriously the color is gorgeous. I agree they go with everything.

  9. Jenny | 31st Jan 18

    I love those riding boots! I totally agree that everyone needs a pair of riding boots.

  10. nikhila | 31st Jan 18

    These look fantastic. I’d love to add these to my collection!

  11. sonal | 1st Feb 18

    amazing boots at such a affordable price…. I also want to buy some riding boot as I dont have one.

  12. justine | 1st Feb 18

    you can never ever go wrong with a pair of riding boots! they totally pull a casual look together. perfect when i have to be fancy but feel bummy ๐Ÿ™‚

  13. Jennifer ~ The Tipsy Mama | 1st Feb 18

    Could not get through Fall/Winter without my riding boots! They can be casual or dressy – definitely a must have!

  14. Jill Conyers | 1st Feb 18

    Riding boots are fashion staple in our house for myself and my daughter. They’re so easy to dress up or cute and casual.

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