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How To Style Boots With Dresses And Skirts

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I don’t know about you, but one of my favorite looks for the fall season is pairing a great pair of boots with dresses and skirts. It’s the perfect combination of comfy and cute, and it’s one of those styles that works for just about anyone, especially us gals over 50! I thought it’d be fun and helpful to put together a guide on how to style different types of boots with dresses and when to reach for each style.

Choosing the Right Dress to Wear with Boots

Now, before we get into the different boot styles, we need to talk about the type of dress you’re going to wear. The dress you choose will determine the overall vibe of your outfit. Here are a few dress styles that work particularly well for us gurls over 50:

Knee-Length Dresses

Tania Stephens is wearing a denim frayed dress with knee boots
Denim Dress (Large) | Cristen Knee High Boot (TTS) | Lex Chain Necklace in Gold | Colette Large Hoop Earrings | Lex Chain Bracelet in Gold | Suede Crossbody

Y’all know I love a good denim dress, but pairing it with these brown knee-high boots takes it to a whole new level! It’s casual meets polished, with a touch of rugged flair. The boots help elevate this laid-back denim look, perfect for anything from brunch to a casual date night. Plus, knee-high boots with a dress create the illusion of longer legs—always a win in my book!

Knee-length dresses are one my go-to lengths! You get just the right amount of leg showing to keep the look fresh and fun without feeling overexposed. Whether you’re going for a more casual vibe with ankle boots or dressing it up with sleek knee-highs, this combination effortlessly pulls together into a polished, put-together outfit.

Midi Dresses

Tania Stephens is wearing a leopard midi dress with tan suede ankle bootw
Leopard Tie Waist Shirtdress (Size 12) | Lex Chain Necklace in Gold | Colette Large Hoop Earrings | Lex Chain Bracelet in Gold | Triple Strand NecklaceFranco Sarto Bootie (8.5)

Who says you can’t mix wild prints with classic boots? I’m wearing these gorgeous suede ankle boots with this bold leopard print dress, and let me tell you—it’s a match made in fashion heaven! The boots help tone down the fierceness of the leopard print, keeping the look chic yet playful. If you’re not ready to go full “wild side” but want a hint of sass, neutral boots like these balance things out while still making a statement.

Leopard Print Midi Dress Styled with Knee High Boots
Leopard Print Cutout Maxi Dress with Long Sleeves (Medium) | Faux Leather Tall Boots) | Faux Leather Drawstring Tote Handbag

Midi dresses that hit mid-calf are another favorite of mine. This length of dress works for everything from church to date night! Plus, if you want a little extra coverage and don’t love showing so much leg, midi dresses have got you covered. I typically wear an ankle boot with mine in the fall, but you could easily grab a knee-high boot if it’s chilly and you need extra warmth.

Sweater Dresses

Fashion Blogger Tania Stephens is styling Fall Fashions from Amazon17
Plaid Long Blazer (Medium) | Cable Knit Sweater Dress (Large) | Knee High Boot (Shop Similar)

When the temperatures drop, sweater dresses are a must. I love slipping into a cozy knit sweater dress and pairing it with my favorite boots—whether it’s sleek knee-highs or casual ankle boots. It’s one of those outfits that makes you look put-together while still feeling like you’re wrapped in a soft blanket.

P.S. If you’re shopping for dresses to pair with your boots and booties, check out these posts!

Styling Types Of Boots With Dresses And Skirts

1. Ankle Boots

Tania Stephens is wearing a leopard pleated skirt with black ankle boots
V Neck Chiffon Blouse (Large) | Leopard Print Midi Long Skirt (Medium) | Leather Shopper Tote | Logo Buckle Leather Belt (Medium) | Camuto Pointed Toe Bootie (TTS) | Colette Large Hoop Earrings | Michele Watch w/Diamonds | Lex Chain Bracelet in Gold 

Leopard print and stylish black ankle boots? Yes, please! This combo is perfect for when you want to feel a little edgy but still stay polished. These black boots add just the right amount of sharpness to the soft, flowy skirt, creating a chic and balanced look. And those pointed toes! They not only elongate the legs but also make you feel like you could conquer the world—fashionably, of course!

Ankle Boots Styled with a Satin Shirt and Skirt for Fall by Tania Stephens
Washable Stretch Silk Split Neck Blouse (Medium) | Relaxed Stretch Satin Skirt (Medium) | Woven Belt | Franco Sarto Bootie (8.5)

Ankle boots are hands down the most versatile of all boots. Whether you prefer them flat, heeled, or with a chunky sole, they look great with any style and length of dress from mini to maxi. I’ve already worn these Franco Sarto booties more than I can count, and I just got them! You can find some of my other ankle boot recommendations in this post.

If you’re going to be on your feet all day, go for a flat ankle boot. Want a little height? Go for a block heel or for a wedge bootie, which is super stable and easy to walk in. And when the temps start to drop, just add tights for extra warmth and coverage.

P.S. For a dressier look, shop for a pair of pointed-toe ankle boots. Bonus points if they are in a glossy finish! This combination is going to look chic and be perfect for adding a bit of polish to your outfit.

2. Knee-High or Over-the-Knee Boots

How to style knee high boots with a faux leather dress
Faux Leather Shirtdress (Similar) | Large Kensington Quilted Suede & Leather Shoulder Bag | Kitten Heel Knee High Boot (Size 9)

Tall boots add a little drama and elegance to just about any outfit, which is why they’re so popular when the weather cools down. I love pairing knee-high boots with a cozy sweater dress, but honestly they look great with any type of knee-length or midi length dress. Just add a handbag and some layered necklaces, and you’re good to go!

I have a lot of knee-high boots in my closet. I have recently started adding some fun colors and textures (like these green kitten heel ones), but I would start with a versatile boot in a neutral like tan or black before branching out to more unique options! You can see some more of my favorite tall boots in this post.

3. Cowboy or Western Boots

Over 50 Fashion Blogger, Tania Stephens, is showing how to style boots with a dress cowboy boots
Denim Jacket (Large) | Chocolate Belt Bag | Junk Gypsy Western Boots – Sold Out

I’ve talked several times about how western inspired clothing is making waves this season. Cowboy and western boots are a fun way to add this trend to your own closet.

You might think this style of boot looks casual with a pair of jeans, but they can actually be quite versatile when you pair them with the right dress! For example, when worn with a flowy midi or maxi dress, they create a bohemian look that’s perfect for a casual wedding or outdoor event. I am also quite fond of how they look when paired with a denim dress! You can see me wearing more cowboy boots with a denim dress in this post.

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Verse Of The Day

Matthew 4:4 NIV
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17 Comments

  1. Tania, what is the dress you are wearing with the cowgirl boots in the last pic? Would love a link for it!

    1. Katie, I love that dress! It was by J.Jill, and it sold out before I could link to it.

  2. sue koren says:

    I love the look of boots with a dress.

  3. Loved the Variety of Looks between the Tall Knee High Boots, Short Booties and Western Cowgirl Boots with the Different Dress Styles. I’d say the one that really caught my eye was the Leopard Maxi Dress with the Dark Red Patent High Heel Knee Boots. I was recently browsing the Jeffrey Campbell Website and saw a Gorgeous Pair of Leopard Print High Heel Knee Boots with Dark Red Patent Accents that looked Beautiful. I’m definitely going to add some form of Leopard Print, either in a Dress, Skirt or Leggings along with the Dark Red Patent Boots for the Upcoming Fall/Winter Season. Love Being a Newly Added Gurly Gurl 🙂

  4. So cute! All the different looks are great!

  5. cute outfits with boots

  6. Thanks for showing us such cute ways to wear boots with dressy and skirts.

  7. So many cute boot choices. I liked the black dress with denim jacket but no link for the dress.

  8. I absolutely love boots with dresses! I’m excited that it’s almost time to begin wearing them.

  9. Boots/dress. LOVE IT!!!

  10. love all the boots!!
    my faves are booties and cowboy boots. I’m trying to figure out how to pair a white cowboy boots without any white pants or white dresses etc

  11. I’m looking forward to wearing my boots, now that the weather is cooler. Thanks for all the suggestions.

  12. Good styling tips. I have short legs so I can’t do ankle boots with a midi.

  13. I love boots with a dress too! Cute choices!

  14. Love wearing knee length dresses with knee high boots. That’s my favorite combination. Because I am petite, I don’t wear ankle boots with anything other than slacks or jeans. If I wear them with skirts or dresses, I look cut off at the leg. 🙂

  15. I love boots, but struggle with styling correctly. Great post!

  16. Love the denim dress!