Stay Warm And Stylish: Best Winter Boots For Petite Women Under $100

Who doesn’t love a good cozy pair of boots in the winter? I have allows loved boots, and booties, I’ll wear them at the first sign of the chill in the air. The first leaf hits the ground and pulling them on, throwing a jacket over my t-shirt and calling it fall. A good pair of boots with dark jeans and a sweater for a classic easy look that will be warm and functional is never out of style. Boots are such a cute go-to item in the winter, and to say I’m obsessed would be a bit of an understatement. Digging through my closet I’ve rounded up my best winter boots for petite women under $100, making your legs look longer and hitting you in all the right spots on your leg. Go, to boots that I wear every year and can’t live without.

I used to think that because I was so petite I had to be wary of buying boots that were too tall or that I couldn’t pull them off. But oh was I wrong. As I’ve gotten older I’ve learned that it is all about the fit of the boot, making sure it hits you right but as long as it does, we petite girls can rock riding boots and over the knees just as well as anyone.

Best Winter Boots For Petite Women

So versatile and easy to wear boots can be comfy and casual or dressed up to rock for a nicer event depending on the style. I blame my mother for my addiction, so thanks, mom. No, but really, I seriously needed to stop adding to my collection because it’s getting a little out of hand, well, can you ever really have too many pairs of boots? The answer is no, I don’t think you can. So after sorting through an ever-growing collection, I have pulled out 7 pairs of boots that you shouldn’t live without this winter.

Riding Boots

Riding Boots-Best Winter Boots For Petite Women

The classic riding boot is a staple must have for fall and winter fashion. I could find my exact ones anywhere online but these Tommy Hilfiger Gesina Riding boots are extremely similar to the ones I have. A good classic pair of riding boots is a must-have to wear with jeans, dresses, skirts, or even leggings. I wear mine to work, running errands on the weekends, date nights and everywhere in between. The best part other than the great quality and price tag is the fact that these aren’t too tall for my petite little legs. They hit in just the perfect spot right below where my knee bends. For around $80 from Nordstrom Rack, these boots are a great addition to any wardrobe.

Cozy Boots

Cozy Boots- Best Winter Boots for Petite Women

While I am a huge supporter of shopping in the kid’s department to save some cash money, I am an even bigger supporter of shopping big sale for quality items. Bearpaw Margaery boots are so comfortable and warm, they are like slippers that are socially acceptable in public. Basically a cheaper version of Uggs boots I’ve had pairs of these last me for years before finally getting worn out. Usually, around $85, I bought mine on black Friday for $35 and you can usually find the style on sale at Nordstrom Rack. The quality is amazing and these boots go all the way down to a size 5 for those of us on the petite side of things.

Warm Boots

Warm Boots- Best Winter Boots For Petite Women

The work boot style has come back with the rise in popularity of timberlands but if you are looking for an option under $100 these MIA Maylynn boots are the answer. They are extremely high quality and have held up will through all kinds of weather proving they are very much worth $60. They are narrow enough that they won’t look chunky or overwhelming on a petite frame but are still that super cute sturdy work boot look. I love that these are warm and can be worn with a variety of different outfits for a cute casual look. Definitely one of the best winter boots for petite women.

Dress Boots

Dress Boots- Best Winter Boots For Petite Women

Looking for some boots to dress up for a special occasion like a Christmas or new years party? These Black heeled booties are extremely similar to a Steve Madden pair I’ve had for years that I am obsessed with. $85  will be well spent on a classic pair of black shoes every girl should have in their closet. The chunky heel makes the sturdy and comfortable while giving us petite ladies a boost in the height department, and they are just so classic and can be paired with any number of special occasion outfits from dresses, to black pants.


Moccasins- Best Winter Boots For Petite Women

My moccasin booties are hands down one of my favorites casual pairs of shoes. Cute, versatile and the perfect addition to any weekend wardrobe, I love these because I’ve worn them with dresses and pants, they look just as good with either. I will say this if you live someplace cold size up so you can wear them with thicker socks and buy some waterproof spray so that the suede doesn’t get ruined by water and the salt on the roads. If you take care of them these cute booties, which only cost $60 will be with you for years to come.

Office Booties

Office Boots-Best Winter Boots For Petite Women

Having a pair of booties to rock at the office is an important part of any wardrobe. Depending on the dress code at your job these can range from dress booties like the ones I mentioned above to more business casual styles. I rocked a similar pair, which are sold out, to these Steve Madden ones to just about every job interview I went to while looking for a job and there is something about them that just makes you feel like you can put on your power walk and have some swagger. $70 for a pair of shoes that make you feel like a queen? Thats a no brainer! Again the heel gives you some extra height but they are so comfortable that I’ve worn them through a full day and never had any problems with them hurting my feet.

Slipper Boots

Slipper Boots- Best Winter Boots For Petite Women

Everyone needs a pair of slippers to wear around the house. Nothing is cozier than a warm pair of leggings, some cute slipper booties and a warm sweater for those lazy days around the house or Christmas morning. Mukluks Scrunchy boot slippers are so warm, cozy and perfect for anyone who likes to be comfortable around their house. They go great with leggings for a lounge day look, and mine have held up extremely well over the years that I’ve had them. $40 well spent on a cozy pair of slippers that are not only cute and patriotic but the fleece lining keeps my toes nice and warm. I haven’t had to replace them yet, they are the perfect amount of oversized to be comfortable while still being small enough to not look gigantic on my feet or so losing that they fall off.

The most important thing to remember about shopping for boots is that as long as they are the right size and you make sure they are hitting you in all the right places, nothing is off limits. It might be harder to find over the knee and thigh highs that aren’t too tall but if you do some digging they are out there, you just have to be patient.

There no occasion where you can’t rock the right pair of boots, whether you are lounging around the house during the holidays, in the office or headed the hottest party of the season. Rock them from work to happy hour, with dresses in the fall to leggings and sweaters in the fall and look effortlessly cozy.

What are your favorite boots to wear in the winter? Do you have an extensive collection or a few pairs you are loyal to?

Hopefully, this roundup has helped inspire you to rock all the best winter boots for petite women, and I can’t wait to see all of your fabulous fashion! Follow and tag me on social media @livinglifepetite to show me how you are rocking some great winter boots this year! I hope you all are having a great Monday and an amazing last week before Christmas!





  1. Jackie

    December 19, 2017 at 4:26 am

    These are so cute! I’m 5’5” and tend to go toward ankle boots to make my legs look longer. I actually have Steve Madden booties and Tommy riding boots like these in my closet. 🙂

    1. Charlie

      December 19, 2017 at 8:52 am

      I totally feel you girl! I am the same way but also love a good pair of taller boots too! Thanks for stopping by girl! Xoxo Charlie

  2. Gillian

    December 19, 2017 at 9:05 am

    I love me a pair of cozy boots.

    1. Charlie

      December 20, 2017 at 6:52 pm

      Me too! My favorite part of cooler weather! Happy Holidays! XOXO Charlie

  3. Karrie Frost

    December 19, 2017 at 9:15 am

    I love these boots. Those mocassins are calling my name! Thanks for sharing.

    1. Charlie

      December 20, 2017 at 6:52 pm

      They are the best!! Thank you so much for stopping by and Happy Holidays! XOXO Charlie

  4. Yen (GlossyCover)

    December 19, 2017 at 9:34 am

    My favorite booties are the moccasins! So cute. I’m only 5’2″ and I think they will go well with many outfits.

    1. Charlie

      December 20, 2017 at 6:51 pm

      I love them so much and they are so versatile! Happy Holidays! XOXO Charlie

  5. Narhee

    December 19, 2017 at 12:01 pm

    Love your picks! Sometimes it’s a struggle to find shoes for my foot size.

    Narhee | Made in Mauve

    1. Charlie

      December 20, 2017 at 6:51 pm

      Thanks! And yeah I totally feel that! Kids section for the win sometimes with those! Happy Holidays! XOXO Charlie

  6. Alina

    December 20, 2017 at 4:59 pm

    Super cute! I am only 5’1 which makes me petite and this guide is super helpful.

    1. Charlie

      December 20, 2017 at 6:50 pm

      I am so glad! I feel like sometimes its overlooked how it can be to find that perfect pair of boots! Happy Holiday! XOXO Charlie

  7. lapetitepoire

    December 20, 2017 at 6:03 pm

    Some of these are cute but none of them are winter boots. Fall boots, maybe. Indoor, definitely. None would stand up to the snow, ice, slush and sleet of winter.

    1. Charlie

      December 20, 2017 at 6:49 pm

      I think they are cute too! Actually, after treating most of these waterproof spray, they have made it through snowy winters in Colorado just fine. I’ve even taken them to Chicago and had them hold up great after walking around the snowy city all day! XOXO Charlie

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