Winters are long and cold in my part of the world. Boot weather starts in early November and lasts until April, so I’ve done my share of buying and trying out boots. January is a great time to buy boots because retailers are marking them down to make room for Resort/Pre-Spring merchandise. Here are 5 classic boot styles that you’ll wear over and over again…

The Bootie

Booties are the shortest boot. They can have any heel height but I’m going to highlight the lower heel styles.  These Dolce Vita Elisa Booties have a roomy rounded pointed toe and a Cuban heel (a low heel that is straight on the inside and angled at the back).  Wear this type of bootie with dresses, tailored pants or jeans.

For an even lower heel, try Vince Camuto’s Pratfina Embellished Ankle Booties.

If you like lighter colors, these Sole Society Azure Booties come in taupe, blue, caramel and dusty rose.

The Chelsea Boot is one of the most classic boot styles. It is a menswear-inspired boot with a wider shaft (looser fit around your ankles) and a flat heel.

The Ankle Boot

Suede, low heeled ankle boots are also very versatile. I’ve been wearing my Banana Republic ones (these are similar) with tailored pants or boot-cut jeans. Match your pant and boot color to give you a longer, leaner look. You can also wear these classic boot styles with skirts or dresses.

For styles that are a little more fitted around your ankles, try a these Aquatalia’s Carie Water Resistant Boots.  

These Sam Edelman’s Hilty Ankle Booties come in an animal print.

These Schutz Gisela Sock Boots are a fun play on athletic socks! These Stuart Weitzman Rapture 75 boots are almost half-price. You’ll need to wear these with bare legs because they are tightly fitted. Plan to wear them with skirts, dresses or (under) wider leg pants.

For classic lace-up boots try these Luck Brand Borelis heels.

The Rugged Boot

Between the snowstorms and summer heat, you’ll need to be prepared for wet and muddy days.  I have these Gumleaf Norse boots which I wear around the farm most of the year. For slightly more fitted boots, I just bought these Frye Harness 12R boots to wear with skinny jeans or leggings, sweaters, and tailored or puffer jackets.

Frye also makes a shorter Harness 8R version and a taller Harness 15R style.

La Canadienne also makes some rugged boots like these Caily ones with a rubber sole to protect you when the ground is slippery.

The Snow Boot

These Sorel Joan of Arc boots are great for snow adventures. Wear these with fleece-lined leggings or jeans and a ski or puffer jacket. They are waterproof, insulated and fur-trimmed. I’m going to wear these for our sons’ ski races because I’ll need to be able to run through the snow to catch glimpses of them as they fly by!

The Over The Knee Boot

There is much debate about other the OTK boot is in or out of style. I continue to wear and love my Lucky Brand Rayla boots that I bought a few years ago. You can still buy them here. The block heel makes them comfortable to wear and adds warmth when you want to wear a dress or skirt. If you are tall, these would also look good with skinny jeans or leggings.

5 Classic Boot Styles: Over The Knee Boot

These Steve Madden Purly Over The Knee Boots are similar and come in black or dark brown .

Classic Boot Styles To Buy

If you’re looking for more great buys, follow my Shoes board on Pinterest, where I’ve pinned more than 50 styles that are available online now (at time of writing).  I’ll post more photos of outfits on Instagram, so be sure to follow me or take a look at this page.  If you didn’t read my last post, you can find it here. As always, feel free to add your comments or questions in the comment box below.  Have a great week! 


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