Three Tips on Wearing Winter Boots with Dresses

Sexy shoes and cute boots aren’t synonymous with comfort.

– Most Women

Many women also unwittingly believe that footwear cannot be sexy, stylish, AND seriously functional. This is especially true during the winter months; the season when women often struggle with wearing sexy and sensible shoes. 

Pairing sexy boots with winter dresses presents an entirely new set of struggles.

I tried several combinations of sexy boots and dresses. My family declared my terrible experiment with a lightweight spring dress and leggings more“frumpier & desperate” than my intended “sexy with effortless style”. I wore black thigh high boots with a stiletto heal paired with dark tights and a short grey sweater dress; again, I heard groans. Determined to conquer the art of effortless styling sexy boots with dresses, I researched and created the following guide.

Tip #1: What Not to Wear

When it comes to sexy boots, my golden rule is to be comfortable. Shoes that are ill-fitting or uncomfortable will shows in your face. The grimace from foot pain will detract from your otherwise well-styled outfit. I was my own worst enemy for a while, at least in regard to sexy winter boots and cute feminine outfits. I wish I listened to my mama and grandma more — wincing and grimacing in pain is never sexy.

More-so than any other season, winter footwear needs to be functional. Well-fitting, functional boots will prevent any distractions from your confident sexy persona. No shoe is so sexy that it can compensate for an expression of pain and disgust. Sexy boots must be comfortable.

Tip #2: Be Comfortable and Sexy in Boots

Being comfortable in sexy boots seems aspirational to many women. My best tip for being comfortable in sexy boots is to try on many styles. Edit out the heel heights and sexy boot styles that just don’t work. Four-inch stiletto heels might not fit into your lifestyle today.

If your determined to rock that sexy shoe of your dreams, learn what it takes to master that style. In fact, there is a great article featuring an interview with Beyonce, she discussed learning to walk in heels. She mentioned she had to teach herself how to walk in high heels.

If your determined to rock that sexy shoe of your dreams, learn what it takes to master that style. In fact, there is a great article featuring an interview with Beyonce, she discussed learning to walk in heels. She mentioned she had to teach herself how to walk in high heels.

So relatable. I mean, how many of us really were born with an innate talent for walking in high heels? Not many, is my guess. Ladies, it is comforting to know that I’m not alone in my quest to conquer high heels.

Learning what works for you (your personality, your comfort, your body) will empower you to expand your sexy shoe horizon. Sexy shoes are best paired with a confident woman. When stiletto high heeled boots weren’t realistic for me, I wore more sensible, functional, and fashionable stacked heel boots. Heck, even cowboy boots will look sexy on a confident woman with well styled clothes. Eventually, I learned how to walk in these sexy stiletto thigh high boots styled with an equally fabulous plaid irregular hem shirt dress.

Tip #3: Avoid Looking Frumpy or Disheveled in Winter Boots

Avoid the obstacles of boots that are an eyesore or sexy boots that provide no protection from the winter weather. Styling winter dresses with cute boots shouldn’t be an issue with my no-fail guide to pairing dresses with boots. Throughout my research in sexy boot and winter dress pairings,

I determined that there are three basic factors to consider:

  • Heel height
  • Boot material
  • Casual to formal design

When it comes to cute boots for winter weather, heel height, formality of design, and the material are the biggest influence in determining its sexiness factor. Too high of a heel heel that are inappropriate for the weather (wind, snow, ice, and rain) degrade the sexy factor. Sexy isn’t limited to the design of the shoe. Being a sexy, stylish lady is also about being on-point appropriate. Assuming the only weather element I have to contend with is cold temperatures, then I say rock the sexy high heeled boots!

The best pairing for high heeled boots and winter dresses must also consider the height of the boot shaft. High heeled ankle boots offer many more options with winter dresses. Mini-skirts, maxi dresses and knee length or midi dresses can pair very well with a high heeled ankle boot. Thigh high boots with a high heel rarely work well with mini-dresses or maxi-dresses. The thin line between sexy and trashy is too easy to cross. Also, long dress hems are too likely to get caught in a high spindle heel (causing a tripping hazard.)

Sexy boots can be made in more than just leather or synthetic leather. Canvas wedge high heeled sneaker boots are a savvy choice for sexy ladies looking for comfort and a playful, casual boot. Lace-up combat boots in olive vinyl or fabric are a utilitarian, military inspired look that can be sexy when paired appropriately. Picture this: a feminine winter dress, dark neutral tights, and peek-a-boo socks that sneak out of the top of the boot. Add a scarf, statement bracelet, belt, and a messenger bag for a sexy boot moment that keeps your grounded in no-slip shoes with style.

Bookmark my basic sexy boot styling suggestions for more how-to’s and tips to amp up your sexy shoe style quotient.

‘One shoe can change your life.’ – Cinderella

4 thoughts on “Three Tips on Wearing Winter Boots with Dresses

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    Maglie Juve Onlin

    • admin says:

      Maglie, thank you for your kind words, we love what we do and absolutely adore our fan base, welcome to the family. We are currently going thru some restructuring phase but stay tuned, we have more great articles, reviews, and shoes to share with you and all of our awesome followers soon.

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