Let’s face it: when it comes to the fall and winter seasons, boots are going to be the shoes of choice. I love boots, and I have them in all different colors. Plus, I have them in several different styles, including open-toe, combat, ankle, moto, knee, and cowboy boots. The area that I have struggled with was how to style boots with dresses and skirts. There are some occasions when only a dress or skirt will do, and the right style of boots can really make the difference.
How To Style Ankle Boots With Dresses and Skirts
I’m starting this post with a classic silhouette. I love a pencil skirt, and this Ponte Midi Skirt looks and feels so nice. This skirt is a versatile workhorse in your wardrobe since it can be paired with so many tops and sweaters. We all need at least one or two versatile skirts for occasions when we have to dress up.
I added a leopard print tank and a Black Long Cardigan to the skirt. The black-on-black outfit creates a long, lean look, and the leopard print adds some fun to the outfit. These are all items I bought during the Nordstrom Anniversary Sale in July, so some items, such as the leopard tank, are sold out. Here are some similar items that would give you the same look and effect.
Since my Ponte Midi Skirt is below my knee, I wanted to show some skin by adding a pair of ankle boots. I prefer to show a little of my leg whenever possible since it helps you to look taller. If you choose to wear a boot that meets your dress, try to wear one with a pointy toe.
How To Style Riding Boots with Dresses and Skirts
I love combining items that seem like opposites. A cute above-the-knee skirt doesn’t seem to go with a Washed Leather Bomber Jacket and edgy Knee High Riding Boots…but I love the look. I have several leather moto jackets, but this is my first leather bomber jacket. I think I like the bomber jacket better. 😳 What do you think?
I love the quilting on these faux leather Knee High Riding Boots!!! These boots are so cute and edgy, and they are also affordable! Since the skirt is above my knee, I can still show some skin even though I’m wearing knee-high boots.
How To Style Knee High Boots with Dresses and Skirts
I’m not sure which item is the star of this outfit. I love the rich color of the Cable Knit Sweater Dress, but the Plaid Long Blazer is gorgeous. Plus, I love suede knee boots, and the color of this pair is a great neutral.
Here is a great example of the boots meeting a dress. From the side view, you can’t see any skin, but from the front view, you can see part of my leg because of the split in the sweater dress. These boots are so pretty in person, and I like that they look great with a dress as well as jeans.
How To Style Tall Western Boots with Dresses and Skirts
Look how cute this casual outfit is!!! I added my favorite Denim Jacket to the Smocked-Waist Ruffled Sateen Dress, and immediately thought I needed to add a pair of western boots to the look. The sateen dress is not Western, but the denim jacket made it look casual.
The dress is a midi length, and you can’t see the boots very well. I wanted to show how pretty these boots are, so I hiked up my dress for a peek.
I don’t wear Western boots very often, maybe once or twice a year. This is the only pair of tall western boots I own, and they are several years old. Because I don’t wear them often, I wanted to pick a pair that was not flashy and wouldn’t bring attention to themselves. I still wanted some style and design details, so this pair by Junk Gypsy was perfect. I’ve linked to some similar ones below.
How To Style Ankle Western Boots with Dresses and Skirts
Denim dresses are trending this fall, and I love this one I bought from Amazon. I bought a lighter color first but sent it back for this Wishful Blue color. This dress is shorter than the others and hits me higher above the knee. A shorter dress is great for Petite ladies who want to show as much leg as possible since that helps you to look taller.
I styled it with these ankle Western Booties that have cute details and a pointy toe. The boots look great with the Italian Leather Triple Compartment Crossbody; the colors coordinate well. We were having a warm spell, so I didn’t add a jacket or cardigan, but I’ll link to a couple below that would go with this look.
Which look is your favorite? Will you wear boots with dresses and skirts this fall and winter???
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