Wearing Boots With Skirts

During the chilly fall and terribly cold winter months, I love wearing boots with my skirts. Here are some reasons why.

The Positives of Boots

~They are stylish. You can find casual or dressy pairs of boots.

~They help keep you warm. Wearing that extra layer is nice!

~You can wear any sort of socks with them, and nobody knows! Seriously, I’ll wear thick wool socks sometimes that normally wouldn’t look very good with mary jane style shoes.

~They go well with leggings under your skirts!

The Negatives of Boots

~Cheap boots are normally not comfortable. I can handle wearing my cheaper boots to church, but they are not something I would want to wear all day long. I have a nicer pair of boots that are cushy on the bottom and I can wear them all day, no problem. But it’s hard to invest in good boots if you have a house full of children that need clothes and shoes also!

Lace and boots! Source

 Boots can be worn with all different styles and colors! This is a very feminine, lovely outfit with adorable looking boots!

Pencil skirt with bootsSource

 I’m not a huge fan of pencil skirts, I don’t even own one. But I have to admit this is a really cute outfit!



A midi length skirt looks great with boots. Sometimes I think midi length looks like an awkward length, but it is perfect with boots.

 Honey Skirt Outfit with Boots

I wear shorter skirts during the winter as I wear tall boots with the skirt and have leggings on underneath.

Source: Skirt: Deborah & Co. Blouse: Deborah & Co. Boots: Zappos

Navy Polka Dots with a little brown
A few more thoughts on boots…
Shop at places like TJMaxx and Marshalls to find a good quality boot for less money. I always see good deals on boots on Black Friday as well.
If you are looking for a high quality boot, some names to look for are Sanita, Bass, and Keen. If you have other suggestions, leave a comment!
Tall boots go with pretty much any sort of modest hem length (knee length on down).
Ankle length boots are in style, and while I’m not a huge fan of them I know it’s possible to pull them off with skirts. I often see them paired with shorter skirts. Here is a longer skirt outfit to give you an idea of what that could look like.
Ankle Length boots with Skirt
I find that putting boots with a skirt or dress is an easy way to dress up an outfit and add a little fashion style without going overboard. Personally, I stay away from boots and heels that are super high as I don’t feel comfortable in them and I also don’t like the message they send.
High Heel Boots
Shoes can be sexy looking, and I find that thin, really high heels can easily add a sexy look to an outfit. It’s ok to look fashionable, but let’s remember the goal is to look modest first, modern second.
Do you like to wear boots with your skirts? Drop me a note below and let me know! 

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  1. I LOVE the long skirt with short boots. What about wearing jackets with skirts? NY winters are brutal, but when I wear my jackets, it seems like my warmest cozy one is too bulky, and my long peacoat is an awkward length with a skirt.

  2. Oh my goodness I love wearing boots and skirts!! I wear skirts 99% of the time, except when we’re hiking and I need jean-like protection from critters & bugs. I had two pairs of boots very similar to the ones in your first & second pictures you posted, and I wore them so much that they wore completely out! Haven’t been able to find a replacement yet … the place I bought them at no longer makes them. 🙁 I’m 19 weeks pregnant with #4 right now, and wearing anything with a heel is pretty much impossible unless the shoe/boot is really comfortable. So, I’m keeping my eyes peeled! Winter is on it’s way…

  3. I love the look of boots with skirts but, have a difficult time finding boots that fit as my calves are quite large…Any suggestions? I have tried to get them at the plus size stores but they are not a very good quality.

    1. I saw lots of wide boots online at Zappos. I’ve always heard their return policy is really good, so maybe give that a try?

    2. 6pm.com has wide and even extra wide sizes available.
      6 pm is a sister site of Zappos. It’s free shipping to you, but not back. They have the same high-end items, but much cheaper than zappos. I can’t remember, but I think I may have seen that explained on zappos.com. I hope you can find what you’re looking for 🙂

    3. My mom also had this problem until she found that Kohls also has a type of boots made with a wider calf. I don’t know what kind of good quality they are, but my mom likes the pair she has!

    4. I have wider calves, as well, & I love my Børn boots! I ordered them online–great place to shop. Zappos is good. Try half.com as they run specials up to 75% off!

    5. Simply be has many calf sizes, you measure your calf and done. Good leather boots. And they don’t make the ankles fat either,

  4. I love all of the outfits you have been showing! I am in love with skirts and dresses and have been for several years. I have struggled recently with finding new pieces to replace pieces i have had for 10+ years. You have been so helpful in showing me how to make my new pieces go so much farther! Yesterday I wore a sweater dress that was about knee length on me (i am 5’1″) and a pair of black leggings and my son asked me why i was all “dressed up”. I love my boots and wear everything from Manitobah Mukluks (super comfy esp if your pregnant and have some swelling) to more dressy boots with a small heel. I don’t wear boots in the house (or shoes) so it’s important for me to have something like the Manitobah Mukluks that just slide on super easy by the door 🙂

  5. I have a pair of pink/burgundy Ariat western boots that I love to wear with long denim or prairie style skirts. I have a pair of furry suede Bare Traps boots that I got at Goodwill. They are comfy and look good with midi length skirts. Than I have a pair of black leather riding boots from JCPenny that I wear for Sunday. My husband got them on sale. I basically live in boots all winter:)

  6. Famous Footwear is another great option for boots. Name brand at discounted prices! And there are always coupons!

    After horrible customer service, I will never step foot into kohls. It should NEVER take THIRTEEN calls to get resolve an issue with a gift card. Worst part? I was lied to the first 12 times.

  7. I have a brown pair from Shoes of Soul (Zulily deal!) that I LOVE! I also have a black pair of boots from Target….I found them on *super* clearance and they were $15 including shipping 🙂 I generally just wear them to church, and I have orthotics that I need to wear with most of my shoes anyways, which makes them less ‘cheap-feeling’.

  8. My husband bought a pair of black cowboy boots for my son on a business trip. The size was marked wrong and they didn’t fit him, but they did fit me! Yay me! I wear them with all of my long skirts. They are incredibly comfortable and you don’t have to worry about pantyhose or if you’ve shaved your legs which is a plus for a busy mom! When they wear out, I’m definitely getting another pair.

  9. I love the look of boots with skirts but haven’t done it yet. I guess I’m just not brave enough, we still have arctic cold here in WI, but I may brave it tomorrow just for the fun of it. I also agree about the “sexy” stiletto boots I can’t wear them because they hurt my legs but they do send a wrong message too 😉 Looking forward to some new outfits to end winter a little more feminine.

    1. I have wanted boots for so long…every year I look and never found any that I loved…. Last month I found some!! Yay!!! And then it took a few weeks to work up the “courage” to wear them.. I really felt like I was taking a big step… Haha!! But I finally put them on with my skirt and I loved it!!! Now to find a black pair of boots…..

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