Best Boots for Fall & Winter 2020

Our Best Boots for Fall 2020

I’m so happy to show off some of the best boots for the fall and winter of 2020 with my Stylish Monday sisters today. This month’s collaboration showcases our favorite boot styles for the 2020 fall and winter season. Down south, our boot season isn’t quite as long as my friends’ who live in colder climates, but let me tell you…I can’t wait for that first crisp, cool morning that I can wear them! Take a look at how we’re styling our boots, and at a few new styles I’ve found for you. Be sure to read through to the end so you can see all the great boot styles and link up with us too! We’re so happy you’re here!

This is not a sponsored post, but does contain affiliate links. I receive a small commission when my readers click those links and make a purchase, which helps to support my blog. As always, all opinions are my own.

My Best Boots for Fall & Winter 2020

How to Style Boots | Fall Boots for 2020
This taupe pair has been a staple in my wardrobe for several years now. I love the neutral color, and how versatile they are. They work with leggings or dresses, or even jeans tucked into them. I love the tall shaft too. They’re so slimming!
How to Style Brown Boots
My brown boots have a cute fringe detail and are a buttery soft suede. I’ve also styled this pair with both pants and dresses. I love mixing brown with black like I did here. They look great with leopard print too! I’ve actually gotten more wear out of them than I thought I would! Get some brown boots y’all! You won’t regret the purchase!
Over the knee boots
This pair of black over the knee boots was an impulse purchase last year, and I’m so glad I pulled the trigger and bought them. They have a lower heel and are just so easy to wear. They’re my go-to weekend boot because they are the perfect mix of edgy style and comfort. I love the taller shaft too, they’re high without being too “hoochy mama” high…if you know what I mean!

Best Boots for Fall & Winter 2020 – Wide Calf Boots

One of my biggest style challenges is that I have large calves, and have to find boots with a larger circumference, which rules out so many of the styles I see. I’m thrilled that manufacturers are finally getting on board and giving us wider calved gals more cute options! I found the taupe pair at QVC, the brand is Marc Fisher, and I love that they’re a wide-calf style, that doesn’t scream out that they’re a wide-calf style! The taller shaft is super elongating too, which is another little style trick.

Do you have wide calves? Here’s a couple of tips:

  • Look for gusseted inserts of stretchy fabric to give your legs more wiggle room.
  • Try the boots on with skinny jeans to make sure you have plenty of room.
  • Look for a taller shaft boot, to lengthen and thin the silhouette of your leg, and avoid boot styles that stop mid-calf (typically the largest part of your calf area)
  • Over the knee boots work GREAT for wider calves! The longer length helps to balance things out and adds sexy length to your legs! Yeah, girl!

Stylish Monday – These Boots Were Made for Talkin’ About!

Here’s how my Stylish Monday Sisters are styling their favorite boot styles! Be sure to click through on their links and to check out their wonderful blogs. This is such a diverse group of stylish ladies…I love our separate takes on our themes each month and always look forward to seeing how they style our looks.

Stylish Monday Boots

Nicole – High Latitude Style – “It was like you switched a button. From one day to the other fall turned to winter – Alaska winter. We are breaking one negative temperature record after the other. Today in the morning, it was -32C (-25.6F). The old record was -24C (-11.2F)  in 1999. Average high is -5C (23F) and average low is -13C (8.6F). Well, obviously, that’s weather, not climate. And it means boots are a Must when you want to wear a skirt. Well, I am a hard-die skirt and dress gal. Thus, I bite the bullet.”

Nancy –  Nancy’s Fashion Style – ” I adore boots and especially ankle boots! These gunmetal ankle boots are one of my favorites! Actually, I love all of my ankle boots. It’s an addiction, lol.”

Julie – Fashion Trends and Friends – “Can a girl have too many boots?  Why of course not!!!  That poses a dilemma as to which to post for this month’s theme as I l love all types of boots and have various styles in various colors!  I opted to share several boot styles that I thought I’d never wear…never say never!  I thought I’d never wear over the knee boots as I felt they made the tops of my thighs look too thick – like muffin top but thigh top – LOL!  I know I’m late to the OTK boots but hey better late than never.  I also thought combat boots weren’t for me.  While I thought others could pull them off well, I just wasn’t feeling them.  That is until I found a Jessica Simpson embellished pair with rhinestone buckles!  If it sparkles and shines, I’m all about it! “

Stylish Monday Fall Boots

Nina – Sharing a Journey – “I love a good pair of boots to create a seasonal look even though the weather isn’t cool. ” 

Ada – Elegance and Mommyhood – “Oh I am dying over this boots & booties post because that’s what I wear for 6 months here in Michigan. Today I styled my new faux suede taupe ruched boots by Target in a monochrome grey+taupe look that matches my leafy background. These boots looked so good with my grey moto jeans from Nordstrom (old) and my leopard tunic sweatshirt by Abercrombie (new). The mauve mini velvet crossbody bag added an additional texture to the look and I love the mild print-mixing with my herringbone newsboy cap.”

Shelbee – Shelbee on the Edge – Boots are my very favorite footwear ever. I am always drawn toward bold statement boots, too. It was so hard to choose which pair to feature for this month’s theme, but I finally settled on these over the knee lace boots from Shoe Dazzle, one of my favorite places to shop for shoes. I bought these a few years ago and they were really tight around the calves, but after losing a few pounds they now fit perfectly. I paired them with a long forgotten taupe chiffon and lace dress from a few years ago. Recently, I have not had much reason to get dressed at all let alone dressed up, so I used this style prompt as a reason to go all out dressy! 

Best Boots for Fall | Stylish Monday

Suzanne – Ask Suzanne Bell – “Everyone needs a classic boot; a workhorse that you can wear every day, day or night – season after season. I own 2 pairs of this classic block heel boot, one brown, the other black from Tory Burch. And though they look alike, they are actually quite different. Yes, they DO have the same heel (which I LOVE), but the brown pair is a slouch tall boot – the black, a side zip classic black boot. I rarely purchase anything in doubles, but these boots are that good.”

Emma – Style Splash – “Boots are my favourite type of footwear and I have many pairs in different styles and colours. I usually prefer darker colours but I’d been looking for a pair of white or cream knee boots for a while when I spotted these on sale. They were too good to resist! I really like the chain detail on the heel…and they make a change from brown and black!”

If you enjoyed this post, you may enjoy some of our previous collaborations. Check them out here:

The Sweater Edit | October Stylish Monday | Fallin’ for Tie-Dye | September Stylish Monday | Colorful Kimonos | June Stylish Monday | Link-Up

Best Boots for Fall & Winter 2020 | Link-Up Party

Thanks for stopping by and checking out what we’re styling this month! Now it’s your turn! Join the fun and link up with us! Show off your style of the day, your favorite fall fashions, or your latest blog post. This is such a strong network of encouraging and supportive women, so jump on in here and rock your styles! Just click the link-up button below to join the party:

You are invited to the Inlinkz link party!

Click here to enter

10 thoughts on “Best Boots for Fall & Winter 2020

  1. Ooh, Andy, you really do have some fabulous boots! I do love all styles of boots from ankle to otk, heeled, flat, open toed, or cowgirl! I want them all. You look fabulous in all of your fall boot styles, my friend. This was a fun theme for November!


  2. Andy,

    Such a great blog! Love your collection of boots and your tips for wide calves! Your post is beautifully set up! I truly appreciate all of your help and your effort in keeping us organized!

    Julie xo

Leave a Reply