High Heels in the Winter – Yes You Can

High heels in the winter timeOkay, so this can end up being a big conversation. Are your friends and family making fun of you for always wearing high-heeled shoes? Do you feel comfortable in high heels? Don’t understand what all the fuss is about? I’m with you. I love high heels, and will probably wear them forever.

In my world, you can wear high heels in the winter, spring, summer, and fall. Granted, some occasions are better suited for something heavier. Not even I would wear heels on a camping trip. But then again, you probably guessed it, camping just isn’t my thing anymore. Used to love it though, for sure.

I can’t tell you how many times I’ve been asked; “how can you walk in those shoes?” or “wow, love your shoes, but I could never wear shoes like that all day.” And I understand, high heels might not be for everyone but that doesn’t mean you can’t wear them from time to time.

Tights, Skinny Jeans or Dress Slacks

If you live in an area where it gets cold in the winter then boots are certainly the way to go. Wearing boots with tights or jeans can dress up the overall look of your outfit. For a little variety, you can add legwarmers over your boots to give the outfit a nice twist. This look is really nice if you’re wearing tights or skinny jeans.

If you have to be a little more dressed up for work, ankle boots can be a nice variation to regular shoes. Either way, since boots come in different styles you can mix and match them to most any pants and still look great. The height of the heel is a matter of taste in my opinion. However, wearing boots with a six-inch stiletto heel to work might not be the best choice, whether for comfort or appropriateness, although it can depend on where you work I suppose.

Dresses, Skirts, and Long Sweaters

Sticking with the idea of colder weather, boots can easily be worn with a dress as well. The more dressed up your outfit is, the more stylish your boots and/or shoes should also be. For example, if you are wearing a long sweater and tights, the boots can be more casual than if you are wearing a dress suit.

With skirts (and long sweaters) ankle boots is another great way to freshen up the look. Again, depending on whether you are using pantyhose or tights, the shoes/boots should match the casualness of the outfit.

Miniskirts and knee-high boots can look good when worn for the right occasion. Just remember, that particular combination is also a favorite with hookers. I’m just saying. Nothing wrong with an outfit like that, just remember there’s a fine line between sexy and slutty. You decide!

Classic is Sexy – Slutty is Cheap

We all want to be noticed, to some extent or another. And as women, we want to feel nice, attractive and sexy it’s only natural. I believe there are a time and place for everything and sometimes when I see certain people out and about, I truly wish they would believe the same. I know this is a little judgmental, but honestly. Just because something is fashionable and looks great on a model, does not mean we can all wear the same outfit, at least not with the same result! There, I’ve said it. So dress to impress, nothing wrong with that, just keep your self-awareness in check. What do I mean by that?

If you’re going on a sexy date with your boyfriend of 6 months you will probably wear a great outfit that compliments what you are feeling, or what you want to say, for that matter. And, no doubt whatever outfit you chose for the evening will look great on you and your boyfriend will think you’re sexy, no problem. Go for it.

But, no matter how many compliments you get that evening, it does not mean that same outfit will be equally perfect to wear at work. That’s what I mean when I say keep your self-awareness in check, and that there are a time and place for everything.

Do’s and Dont’s – Confidence With a Twist

  • First, learn to walk in high heels. That’s right, it takes practice. Not just to maintain stability, but to also to look “normal” when you walk. I have seen women in shoes that look great but then they walk as though their knees can’t bend. I’m not sure how that happens, but it does, and I see it all too often.
  • Use good judgment when paring shoes/boots with your outfit. Sometimes the shoes/boots complement the outfit, and sometimes the outfit complements the shoes/boots. Keeping it simple prevents the two components from competing with each other.
  • If you’re not sure what looks good: Check out Pinterest or Google the internet for fashion images/pictures. Take note of the images you like, then ask yourself why you like a particular look, and would it work with what you have in mind?
  • The better you know and understand yourself, the more likely you are to not only chose the right outfits for you
    but also feel more comfortable wearing your outfits.

Find Your Own Style

Wearing high heels in the winter time can be stylish, comfortable, and sexy all at the same time. At least when used with some common sense. And, thanks to the internet we now have the luxury of “window shopping” a lot of footwear to ensure we find exactly what we want.

Sexy doesn’t always have to be the stiletto style. These days there are so many variations of high-heeled shoes and boots available I have no doubt you will find your particular style in no time.

When in doubt, to complete any outfit just match your footwear with your purse/bag and you’re good to go.

I would love to hear from you, whether it’s a comment on this article, a question, or maybe a fun (short) story of you wearing high heels?

Thanks for reading,




    • Hi Amanda,
      I understand. The day will come where I might have to capitulate on wearing them as well. However, until then I’ll be in heels:)

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