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8 Ways to Wear Black Riding Boots

February 8, 2019

Welcome to Dressed for My Day! I hope you find a little something here today that you can use. Maybe a little something that will inspire you or help you put together some pieces in your closet in a new way. While we’re deep in the middle of winter, I thought it would be a good time to share 8 ways to wear black riding boots. Of course, you can apply these outfit inspirations to your riding boots of other shades as well.

Let’s get going!

What are riding boots exactly?

Riding boots are the equestrian inspired, classic boots with a sturdy, usually rounded, toe and, traditionally, a low stacked heel. However, some consider riding boots to be any fashion boot that hits just below the knee. So if that’s your definition, your riding boots could have a stiletto or wedge heel, too.

I.n.c. Fawne Wide-Calf Riding Boots

Throughout this post, I’m wearing the I.n.c. Fawne Wide-Calf Riding Boots in black. However, at this point they are only available in one size in the black. They have a few more sizes in other shades. I’ve enjoyed these boots, but they’re not my favorite ever. They’re definitely comfortable, but I wouldn’t mind a little more styling. I do prefer a clean cut boot, however, so these have served that purpose beautifully.

I’m including a widget at the end of this post with plenty of other riding boots. If you’re looking for a pair of boots, now is definitely the time to buy. Most are reduced significantly. The tricky part will simply be finding your size. I do think a good pair of riding boots is a wise end-of-season investment because styles won’t change much next year.

Now let’s see how I’ve styled my riding boots this year.

Black riding boots with black jeans & puffer vest

black comfort denim jeggings // plaid shirt (similar) // puffer vest (similar) // crossbody bag (similar)

One of my favorite ways to wear my black riding boots is simply with black jeans. Here, I’ve topped my black jeans with a red, white and black plaid shirt and my red puffer vest.

black riding boots with black jeans

Tip #1 – When looking for a pair of riding boots, choose a neutral shade that you wear frequently already. If you wear a lot of black, great. Go for black. But if you’re more prone to wear cognac belts and carry cognac handbags, go with that shade. But many boots also come in grey, navy, brown and beige.

Black riding boots with black jeans & black blazer

While the above look is decidedly casual, I simply switch out my red puffer vest with my black blazer when it’s time to up my game a little.

black riding boots with black jeans
black comfort denim jeggings // plaid shirt (similar) // black blazer (similar) // crossbody bag (similar) // leopard print belt

Tip #2 – Keep in mind that riding boots, when worn in the equestrian ring, traditionally are paired with a blazer. So pairing your boots with a blazer is a given! You can wear this combo with a turtleneck, a long sleeved tee or a button up shirt. And your blazer could be black, brown, tweed, plaid or another solid color.

black riding boots with black jeans

Riding boots with blue jeans

black riding boots with blue jeans
floral camp shirt || jeans || black cardigan || black riding boots (wide calf or regular fit – more in the widget below) || sunglasses || handbag (similar)

As I mentioned in this post, I had a bit of a fear about pairing blue with black. But my black riding boots definitely work with blue jeans, too.

black riding boots with blue jeans

Tip #3 – The key to wearing black boots with blue jeans is simply being intentional. When you wear your black riding boots with your blue jeans, try to add at least a touch of black elsewhere in the outfit, too. And the more black you can include in the rest of the outfit, the more coordinated it will look.

Black riding boots with colored jeans

black riding boots with colored jeans

Perhaps one of the easiest looks to pull off with black riding boots is wearing them with colored jeans. Whether the jeans are cranberry red, like mine, or burgundy, green or even white, the contrast is striking. The key is simply to add more black elsewhere in the outfit if possible. Even if you just carry a black handbag or wear a black belt, that extra splash of black brings it all together and makes you look more confident.

black riding boots with colored jeans
black blazer (similar) || cranberry jeans (similar) || grey turtleneck (similar)|| black boots (similar; higher inventory) || black handbag (similar) || necklace (similar)

Tip #4 – When you wear your riding boots over jeans, make sure you choose skinny jeans. Nothing looks more frumpy than to have your jeans riding up and crumpling above your boots. Look, no jeans are going to stay perfectly flat inside your jeans. But you definitely want to minimize the bunching. 

Riding boots with a print skirt

I was at a speaking engagement in Pennsylvania when I saw the women’s minister wearing a silky print skirt over riding boots. I thought she looked so smart. She looked both feminine and confident. I knew I wanted to emulate that look some day.

black riding boots with a print skirt

Nothing from my look is available any more, but I’d say the skirt my friend was wearing was something like this. She was wearing something with a bit of a flounce to it.

black riding boots with a print skirt

Tip #5 – Wear your riding boots with a feminine flounce skirt. The juxtaposition creates an interesting look without looking far fetched. If your skirt has a print or lots of detail work, keep the top simple and streamlined.

Riding boots with a wool skirt

black riding boots with a wool skirt
Red A-line Skirt (similar) || Black Cardigan with Black Stretch Cami underneath || Hue Black Tights || I.N.C. Black Riding Boots in Wide Calf || Black Satchel (similar) || Holly Berry Plaid Silk Scarf (similar, non holiday option) || Gold Shimmer Bangle

The absolute easiest look and by far the most comfortable is this simple wool skirt and sweater paired with tights and boots. I love the school girl appeal of this look, but I still find it contemporary, flattering and grown-up.

black riding boots with a wool skirt

Of course, I showed this outfit in this post about how to add a Christmas scarf to a basic outfit for some holiday flare. But you could add any pretty scarf as a completer. Or sometimes I just keep it very basic and add only a silver necklace.

Tip #6 – When pairing your boots with tights, you generally want to wear tights in the same color as the boots for a long leg silhouette. However, you can also wear tights the color of the skirt if you prefer. That might especially be preferable if you have a long torso and you want to create the illusion of a longer bottom portion. 

Riding boots with leggings

black riding boots with leggings
ponte knit leggings || leopard print blouse (similar) || open front cardigan (similar) || black riding boots (regular and wide calf) || black crossbody bag (similar)

When I posted this post about leggings, most of the readers who chimed in said they love wearing their leggings with boots. While you can wear leggings with flats, too, riding boots truly are a perfect choice to accompany these slenderizing “pants.”

black riding boots with leggings

Tip #7 – While black boots obviously look great with black leggings and brown boots are perfect with brown leggings, you can certainly mix and match, too. For instance, you can wear these black boots with black, brown, grey or burgundy leggings. Just try to add a little of the color of your boots elsewhere in the outfit, too, if you can. But if you can’t, no big deal!

Riding boots with a dress

While a sweater dress is my favorite type of dress to pair with riding boots, you can also find other suitable dresses to wear over your boots. I go with dresses in more hearty fabrics.

black riding boots with a dress

I am so surprised that this dress is still available, but it is. And it’s marked so far down it’s crazy. It comes in red and sparkly grey donegal knits, too.

black riding boots with a dress

Tip #8 – Tights are optional with your dress. I prefer to wear tights almost always when I wear a skirt or dress with my boots because I’d rather my “winter legs” not be seen! But you can certainly go without the tights.

Shop this post

I hope you enjoyed today’s post. I linked to the items in the pictures above when they are available or I could find suitable substitutes. But you may have noticed that some items simply have no links. That’s just because I couldn’t find anything comparable. Also, be sure to check out the shopping widget below for some great deals on riding boots. Because it is the end of the season, some items may sale out fast. Of course, these links are affiliate links, and I do make some income if you shop through them. But you will not incur any additional cost for using them. Thanks so much for shopping my links. And thanks for visiting Dressed for My Day today!

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I’d love it if you took a minute to subscribe to the Dressed for My Day community. You can receive either a daily or weekly email alerting you to my newest posts. Plus you’ll have access to my Freebies for Subscribers. I try to treat my subscribers extra special. In fact, each month I randomly draw the name of one subscriber to be the subscriber of the month. She wins a $50 gift card to a favorite retailer. That could be you!!! You’ll find all the details here.

Blessed for My Day

Today I’d like to share a writing that a friend and subscriber, Sherry Harig, did during her quiet time with the Lord one day. I think it speaks to us the words that our Lord surely feels toward us, for every line is based on His Word. These words remind me of the depth to which we are known by God and yet loved by Him, too.

Lean Into Me

   The closer you are to Me, the more you will know who I am and who you are to me.
I know you like to please…
  Please Me.
I know your endurance…
  I am there along the way.
I know your sacrifice…
  I hold all the things you laid down.
I know all that you left behind…
  I went ahead to show you more.
I know your trust in Me…
  I protect you.
I know your simple prayers…
  They are precious to Me.
I know your strength…
  I am the One who holds you up.
I know your tender heart…
  I treasure your tears, they are sweet.
I know your curiosity…
  I have much to show you.
I know your willfulness…
  My Word tethers you to My Truth.
I know your gifts…
  I will fill your baskets full.
Received from my Lord, January 29, 2019.
Sherry Harig
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xoxo, Kay
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10 thoughts on “8 Ways to Wear Black Riding Boots

  1. I love all these looks. It took me awhile, but a year ago I found a great pair of black riding boots at Nordstrom (and since it was already January, they were on sale). I wear them with leggings, black skinny jeans, and sweater dresses. I wish I could wear them on snowy days here in New England, but I have to wear snow boots instead. I am looking for some skirts since I realize I have none that “give me joy”. Hard to find skirts since I carry some weight in my middle. Thanks again for this post.

  2. Love my black riding boots. Thanks for inspiring me to wear them in new ways! Love the prayer today. And, as always, love you!

    1. I thought you looked so beautiful when I saw you in the fall and you were wearing your black boots with that dress and cardigan. Classy! ?

  3. I would love to own a pair of riding boots, but my feet are very narrow, paper thin, and I have high arches, so finding some that fit and are comfortable, is very challenging. I really like all of the ways you styled them!

    1. Huh. I saw a boot yesterday when I was writing this post and one of the reviews said it fit a very narrow foot. But I have no idea which one it was!!

  4. Beautiful BFMD! “Lean into Me” seems to be God’s wonderful, recurring invitation! I will save this. Thanks for the boot inspiration too!

  5. This was just wonderful to see many ways to wear one pair of boots! Thanks for your tips on each look! I appreciated that you shared you got a look from a friend reminding me that if I can’t come up with something maybe a friend can! we are not I this alone!