Women’s Fall Boots 2020

As a personal styling consultant for women, I make it a top priority to stay on top of current trends and classic footwear to find the perfect balance of styles that are functional, stylish, and durable.

Check out these top boot picks for women as fall quickly approaches.

Vegan Boots
vegan boots for women fall 2020 recommended by Next Level Wardrobe

My recommendation: Matt and Nat Denver Rainboots | Zappos


Winter shoes shouldn’t just serve you well in harsh weather, but should also be stylish and functional.

These shiny black beauties are just the right amount of flashy without being over the top, and make a great alternative to a traditional rain boot.

The shiny patent material can need some additional breaking in, so wear your new vegan shoes for short periods of time, building up to longer walks or stretches throughout the day.


Vegan shoes are made without any animal parts or byproducts, and these shoes offer a simple and well-structured man-made liner, as well as moderate arch support.

Not all rain boots have that, and can become painful to walk in through wet city streets. The plaid detail allows for a bit of texture and style beyond a typical rain boot, and provides stretchy elastic for an easier time pulling on the boot.

Over-the-Knee Boots
over-the-knee boots for women fall 2020 recommended by Next Level Wardrobe

My recommendation: Lowland suede over-the-knee boots | Net-a-Porter


Every woman needs a powerhouse boot, and this is the one to buy of all the picks for fall 2020.

Boots have that amazing effect on women, and if you aren’t utilizing their power to level up any outfit, you need to start now.

The over-the-knee style is a bit more fashion-forward, but also the most versatile pair you will have in your closet. Pair these with dresses, skirts, pants, and leggings in core colors or prints.


Suede is one of my secret weapons when helping clients level up their wardrobe, from suits to jackets. It adds depth and interest to outfits which could otherwise be seen as a bit plain.

The one downside is that suede is a more sensitive fabric, and not one you want to be caught outside in a snowstorm wearing. Plan your more ambitious outdoor plans in the fall and winter around a different pair of boots, and save these for inside.

These boots are made in Spain from supple suede and offer a tie back behind the knee for a more personalized fit. This means you won’t have to worry about gaps at the opening or a too-tight feel for most body types. Instead, you can customize them to the tightness you prefer with the ties.

Textured Boots

textured boots for women fall 2020 recommended by Next Level Wardrobe

My recommendation: Jimme Leather Ankle Boots | My Theresa


If you’ve been following my recommendations for creating a capsule wardrobe, you know that the place to get bold is through your accessories, like these mock-croc designed chunky heeled boots.

This is a great example of getting playful, but not over the top, with accessories, prints, and materials.


I value function with my personal styling clients, and this fits the bill with its square toe to avoid pinching, and a block heel from some height with added comfort. Entirely made of leather and crafted in Brazil, these shoes feature a hidden zipper for easy removal.

Be aware that they run on the narrow side, so they may not be the best choice if you have a wider foot.

Pair these fun boots with rolled jeans or your favorite dress to elevate your workplace style and to show your personality during a night out.

Flat Boots
flat boots for women fall 2020, recommended by Next Level Wardrobe

My recommendation: Frye Veronica Combat Boots | Shopbop


Every woman needs a brown and black pair of boots.

These two colors will give you the versatility to pair everything in your closet into a variety of outfit combinations without having to spend money on many pairs of boots. After all, we are working towards minimalist closets, not piles of boots.

These are a great option because they are flat, and they align with the busy, on-the-go lifestyle most of us have which place comfort as a top priority throughout the day.


Frye boots are made to last, and to withstand some weather, making them one of my top boot picks for women.

The low stacked heel will keep you comfortable running errands or on your commute to work, and the ties ensure comfort and warmth through cold seasons up through your calves.

Combat boots have a more serious and sturdy profile but don’t be afraid to pair these with more feminine pieces, such as a skirt or dress.

Picture of Cassandra Sethi

Cassandra Sethi is a NYC Personal Stylist and Image Consultant. After working over 15 years in the Fashion Industry, most recently as a Senior Buyer for Equinox, she created her business, Next Level Wardrobe – a luxury personal shopping service for successful professionals.

Next Level Wardrobe has been featured in Wall Street Journal, Today and CNN. See here.


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