2020 Winter Boot Trends – Styles to Ditch and Buy Instead

lindsay giguiere, winter boot styles and looks

If you’re anything like me, you have a closet full of boots. Some, from lifetimes ago and others, on the newer side. You’ve developed such a collection over the years that when one style’s in, you can go shopping in your own closet. When one style is out, you put those bad boys to the back of the closet.

Recycling boots season after season takes caring for them year after year. Sometimes you just feel like introducing a new pair to the gang. That said, your closet only holds so much so who’s leaving and who’s staying? These are tough choices for a girl with a shoe addiction, but we’ll help you get through it. If you need me to store any boots for you, I’m happy to offer my closet, but for some reason, only size 7 will fit. Weird how that works.

If you do your research, you’ll be confused. One source tells you suede over-the-knee boots are a hot item this fall and winter, while another will tell you to replace them with knee-high boots. Who do you trust? The answer lies within. If you like a pair of boots in your closet, wear them. Start a trend. If they’re from 1985 and clearly need some TLC, perhaps you should ditch those.

The last thing you want to do is walk into a supermarket only to realize a trail of soul crumbs has been left behind from the bread to the dairy section. Can we say clean up on aisle two, three, four, and five? I think a piece of my inner soul and pride was also lost that day. Well-made shoes will last a long time. Shoes that aren’t well-made will reveal their truth and sometimes, the truth isn’t very pretty.

The number of choices for boots is insane and you can’t possibly have one of everything. I mean, you could, but you may not be eating this month.

You have hiking boots, ankle booties, pointy boots, flat boots, Chelsea boots, rain boots, I need to impress boots, snow boots, I’m sick of COVID and can’t wait to get glam and go out boots, platform boots, I spent all my rent money boots…the list is literally endless.

This year and into 2021, you’ll see boots that are bolder, more fun, and colorful. Fashion should be fun so celebrate with a new pair…preferably in a size 7 so I can again, wear, I mean, store them for you.

To decide where to spend your money, first figure out what you need your boots for. Do you live in a city and walk a lot or are your boots spoiled and barely touch the ground? Are these everyday boots or weekend “check me out” boots? Do you want to hide your calves or show those babies off? Lots to ponder here, so let’s get to it.

You can’t go wrong with chic shearling this winter, no matter the height or color. Grab a pair or three and enjoy the furry goodness on your feet.

Remember Dr. Martens? Did they ever really go away? Combat boots are what you’ll see a lot of this season. They’re practical, go with anything, and last!

Animal prints have and will always be in style. This winter, any will do. The reason I’m such a fan is they go with everything, add a little flair to any outfit, and don’t show wear and tear as much as other looks.

If you rocked high heel boots last season, don’t give them away but don’t pay them too much attention right now. They’ll always look sexy and slimming, but you’ll notice a smaller heel around town referred to as the “kitten heel”. You can go from work to wine and actually handle the height all day. These boots go with everything, including tights and a mini-skirt, which I just love for the colder months. I feel chic, sexy yet tamed, confident, and comfortable. What else does a girl need?

I just gave away a pair of lace-up booties last year and I’m regretting it. I didn’t wear them for many seasons and of course, now, they’re back in style. Hey, you can’t win ‘em all, right?

If you don’t have tons of options in your closet to choose from, don’t feel like a square. Speaking of, square is in and round is out. I know, it’s a lot to take in. All these boots cost money and as mentioned, cheap is not the route to go.

There are so many great consignment shops around where you can swap your old boots for well, older boots. The good news is they’re cheaper and worn in and remember everything always comes back in style. Right now, someone just discovered those lace-up booties at their local store and is ecstatic. You’re welcome. Another idea I love is to swap with friends who have the same shoe size as you. Remember folks…size 7 here.

Is someone going to judge you for not wearing the coolest and trendiest boots? Maybe, but who cares. If you can’t update your boots, update something else in your closet. Perhaps some costume jewelry could be a fun addition to your tired collection. Maybe a new puffer jacket or a cool scarf would make you feel hip and looking your best.

If you can add one new pair of boots to your flock this season, awesome. If not, dig through your closet to see what’s been hiding. You never know what you’ll find.

Wear what makes you feel beautiful and secure because that look never goes out of style.

Hope You Enjoyed the Read!

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Authored By: Lindsay Giguiere

Lindsay is an entrepreneur, influencer, and advocate with a passion to help women and their loved one’s thrive beautifully.


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