Fall and winter are easily my favorite seasons to get dressed for and shoes play a big role in that. A great pair of loafers, boots, sneakers or ballet flats can completely change an outfit and over the years, I’ve become much more intentional about investing in shoes that are both stylish and practical.

Living in New York City means I put my shoes through their paces — literally. I walk a lot, travel often and want shoes that can work with multiple outfits in my closet. I’m always looking for pairs that are comfortable enough to actually wear, versatile enough to style with jeans, trousers, skirts and dresses and well made enough to last for years.

The Best Shoes for Fall & Winter

Below I’m sharing the best shoes for fall and winter from my own wardrobe, including the pairs I reach for year after year, the styles I find most useful and a few more recent additions I’ve been loving.

From everyday sneakers and classic loafers to ballet flats, ankle boots and knee-high boots, these are the shoes that earn their place in my closet season after season.

If you’re interested in seeing more of my collection, you can also read My Favorite and Most Worn Shoes + How I Take Care of Them post.

Essential Fall & Winter Shoe Styles

If you’re building out your shoe wardrobe for fall and winter, I don’t think you need dozens of different pairs. Instead, I like to focus on a handful of versatile styles that work across different occasions and with much of my wardrobe.

For me, the essential fall and winter shoe styles include:

• An everyday sneaker: Something comfortable enough for lots of walking but polished enough to wear with jeans, trousers and even dresses. I tend to favor classic leather sneakers as well as suede styles come fall.
• A classic loafer: One of my most-worn styles during the transitional months. Loafers instantly make jeans or trousers feel more pulled together and are great for days when you want something polished but still comfortable.
• A ballet flat: Ballet flats have been a staple in my wardrobe for years. I love them with denim and trousers in particular and they’re an easy way to make an everyday outfit feel more feminine.
• A slingback: Whether flat or with a small heel, a slingback is one of my favorite ways to dress up denim, trousers or a dress without committing to a higher heel.
• An ankle boot: I reach for ankle boots constantly once temperatures drop. A streamlined pair works beautifully under jeans and trousers while a pointed toe or kitten heel can make them feel a bit dressier.
• A knee-high boot: One of my fall and winter wardrobe workhorses. I wear mine most often with skirts and dresses and love both leather and suede depending on the look.
• A weather-friendly boot: Living in New York means inevitably dealing with wet, messy weather. A practical water-resistant boot that I can walk in without worrying about ruining it is a must for me.
• A dressier heel: I don’t wear heels every day, but I like having a comfortable pump, slingback or kitten heel that works for dinners, events and holiday dressing.

The exact styles that make sense for your wardrobe will of course depend on your lifestyle and how you like to dress, but these are the categories I find myself relying on year after year.

Classic, Go-with Everything Sneakers

By now you all know I love these sneakers and have worn them an almost embarrassing amount since first purchasing them in 2017. I now am onto a second pair after much love. I bring them on pretty much every trip since they are so versatile. A heads up that the sizing on the sneakers is funny – I took them in a size 36 when I’m usually a 37 in European shoes.

A full review of them is here and the post also includes more affordable alternatives, too.

Gucci Loafers & Mules

These Gucci loafer mules are an iconic shoe you won’t regret. I wear these once a week at least and love that they are so simple to slide on and instantly elevate an outfit.

Better yet? They go with pretty much every one of my favorite pair of jeans. I sized up to a 37.5 in these. 

And the classic Gucci Loafers will never go out of style.

Another pair I own and like are these classic Freda Salvador loafers. A bit preppier in style.

Use code WITWHIMSY10 for 10% off your first Freda order!

Affordable Loafers

For a more bearable price point, try Sam Edelman’s gucci-inspired loafers. 

They are also available via Amazon. Loads of color options, too!

Casual Sneakers

Another sneaker I love for Fall & Winter for their versatility and style is these Veja Esplar Logo Sneakers. Not as buttery soft leather or as versatile as my Common Projects but a great more casual sneaker.

And this pair I newly own and love, too.

Adidas Sambas and Adidas Gazelles

I’ve amassed a small collection of Sambas. This sporty sneaker is great with a jean or a trouser and so comfy. I also own the Gazelles that are equally great.

Converse

A great fall and winter shoe and one I like for travel as well as if it rains I don’t mind them getting wet and the canvas dries out quickly.

The perfect cool French girl inspired sneaker.

Related: French Inspired Wardrobe Staples For Fall

Block Heel Slingbacks

Every year for my birthday I buy myself a gift and back in 2017 it was the Chanel slingbacks. I thought about these shoes for several years, tried them on several times and never bit the bullet. Now, I can’t imagine my shoe collection without these because I wear them so much throughout the year.

They elevate every outfit and can go with jeans, dresses and trousers all through Fall and Winter just as easily as they can pair with a pretty summer midi dress. They’re comfortable because of the low, stacked heel and can put up with the many steps I take in them running around.

If you like the style and not the price, this is a more affordable option.

Related: What to Wear with Chanel Slingbacks

Flat Slingbacks

The Chanel flat slingbacks are a more walkable version of their famed style and I particularly love how they pair with jeans.

Shopbop has a variety of similar styles you can shop.

Kitten Slingback Heels

An easy way to elongate your silhouette, theses suede mules (size down half a size if in between sizes) are excellent.

You can use code MEGHAN15 for 15% off your purchase of Inez shoes.

T Heel Boots

The Staud Wally boots have become one of my favorite pairs of ankle boots thanks to how comfortable they are. I love the distinctive T-shaped heel, which makes even a simple jeans-and-sweater outfit feel a bit more interesting.

Staud has offered this silhouette in a variety of styles and colors, including a knee-high version I’ve had my eye on.

Black Suede Sock Boots

These booties were the best pair of shoes I bought in 2017 and they still get as much wear from me nearly ten years later which speaks to investing in classic, comfortable styles. I can go for miles and miles without any issues with these little booties and I love styling them with both jeans as seen here or with dresses and skirts.

I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week. 

Kitten Heel Boots

I’d always heard good things about this brand and eyed a lot of their styles so finally invested in this on-trend, yet classic pair of oh so comfortable and walkable boots. The leather is gorgeous. 

If you prefer a block heel, try these.

I also love J.Crew for a kitten heel bootie. 

Pointed Toe Suede Boot

If you prefer a pointed toe, the Margaux Downtown Boot is perfect for you. Margaux’s Downtown Boot features a stacked heel and a low shaft. The Chocolate Brown color is so beautiful but they have additional colors, too.

Also consider Madewell for another great suede boot.

The Feminine Flat

The Sarah Flint Natalie Flat is a go-to shoe for me year round for its feminine silhouette and comfortable design but it gets the most wear in the Fall. I own this shoe in multiple colors.

Code SF-MEGHAND15 for 15% off your purchase!

The Suede Ballerina 

The perfect neutral flat in a delicate suede. I sized down half a size in this pair. 

Or, try this similar pair at a more affordable price point.

The Leather Knee High Heeled Boot

A timeless style to pair with skirts and dresses, the Loeffler Randall Goldy Boots are so stylish and so beautifully made.

They are also available in a gorgeous cognac color. 

If you prefer a lower heel try this pair.

The Stylish Sock Bootie

These Inez booties are so comfortable and I love the perfect neutral color of them in Ginger Suede. I first bought this style back in 2019 and loved it so much that I eventually added the Black to my collection, too. They’re one of those boots I can walk in for hours without sacrificing style. 

You can use code MEGHAN15 for 15% off your purchase of Inez shoes.

Golden Goose Sneakers

My favorite sporty-chic sneaker. These Golden Goose sneakers are so easy to slip on and I love how they look with everything from skirts to dresses to jeans and leggings. 

Suede Sneaker

I’m particularly into suede sneakers for fall and winter. I love how the texture makes even a casual sneaker feel a bit more elevated and they pair beautifully with everything from denim to tailored trousers. I’m wearing these Vince sneakers above, but the brand has so many great options. I particularly love suede sneakers in chocolate brown, taupe and other rich neutrals for the cooler months.

The Ballerina Mules

Delicate and feminine, I love a bow mule with blazers and denim. I own this Manolo Blahnik pair. I sized up a half size. This is a style I wear most in Fall but that also carries in Springtime, too.

The Perfect Pump

One of the most comfortable pairs of heels I own = the Sarah Flint Perfect Pump. Expertly crafted with comfort in mind, the soles feel like little clouds which makes scooting around town easy, breezy in these. 

I also love that they come in three heel heights and multiple colors. I own the Black, Taupe, Espresso & Red. As well as several limited edition holiday styles they’ve released over the years! I truly believe this is one of the best pairs of shoes you can invest in.

Suede Knee High Boots

And for dressier looks, I reach for these gorgeous Larroude boots. They are so comfortable and chic.

In a similar style but with a more walkable heel, see these suede boots. 

Also I love the soft brown color of this pair by Inez.

Dress Boot

Every girl’s closet needs a pair.

The Sarah Flint Dress Bootie is the quintessential bootie for dressier occasions all Fall and Winter. Designed with extra foot padding these are comfortable and just so beautifully made. I have gotten so, so much wear out of these booties since I’ve owned them the last several years.

They also have a lower heel version if you’d prefer that.

Code SF-MEGHAND15 for 15% off your Sarah Flint order.

Mule Kitten Heel

Not the most practical shoe I own but I sure do love these mule kitten heels by Manolo Blahnik.

I’m already eyeing another color!

Classic Ballet Flats

These Chanel ballet flats were an investment pair of shoes I thought about for a long time before I actually bought them in 2016. These flats are so comfortable, have the prettiest design that goes with so much and make any outfit look a bit more dressed up.

I now own the two tone pair and the all black leather/patent combo seen above. I size down half a size in these.

I also own a similar pair that is less expensive by Margaux.

Or try this pair for a good looking alternative.

The Waterproof Lug Boot

Water resistant suede? Yes please! These Freda Salvador boots are so lightweight making them perfect for travel and oh so practical. Super comfy, too. I wear my true size.

Code WITWHIMSY10 for 10% off your first Freda order.

Khaite Sneakers

Another favorite pair of sneakers I added to my collection that are a bit more sporty are the Khaite suede paneled low top sneakers. They are perfect to style with dresses or trousers and I’ve even worn them with leather pants for a juxtaposition.

Toteme has a similar looking pair as does Maison Margiela. 

The Riding Boot

I love a riding boot in certain settings. I’ll often wear mine with skirts. 

My favorite pair I own are the Sarah Flint Riding Boots that are so classic, so comfortable and feel like they get better with wear. Given their price point I am grateful for their timeless make and style. I wear them so, so much in Winter in particular. 

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What Shoes to Wear With Fall Outfits

One of the reasons I’m willing to invest in shoes is because I want them to work hard in my wardrobe. I’m rarely interested in a pair that only works with one specific outfit. The best fall and winter shoes in my closet are the ones I can style multiple ways.

With straight-leg jeans: I love loafers, ballet flats, sneakers, slingbacks and ankle boots. If I’m wearing a boot, I generally prefer a more streamlined silhouette that fits nicely underneath the hem of the jean.

With wide-leg jeans and trousers: Sneakers are an easy everyday option, particularly a slim leather or suede pair. I also love a pointed-toe boot or slingback peeking out beneath a wider hem for a slightly more polished look.

With dresses: Knee-high boots are one of my favorite pairings once the weather cools down. Earlier in fall, I’ll also wear dresses with ballet flats or slingbacks and for something dressier, a classic pump always works.

With skirts: Depending on the length and silhouette, I’ll reach for loafers, ballet flats, riding boots or knee-high boots. I particularly love the juxtaposition of a mini skirt with a more classic riding boot.

With leggings: This is where I tend to lean sportier. Sneakers are my go-to, but I also love a substantial boot with leggings, an oversized sweater and a great coat in colder weather.

For travel: Comfort is always the priority, but I still want to feel pulled together. I most often pack versatile sneakers, loafers or ballet flats and, depending on the destination and weather, a comfortable boot. I try to choose shoes that can be worn with several of the outfits I’ve packed rather than bringing a different pair for every look.

Related: Easy Travel Outfits

Ultimately, I think the best shoe is the one that makes the rest of your wardrobe easier to wear. If a pair works with your favorite jeans, your go-to trousers and several dresses or skirts already hanging in your closet, chances are it will earn its keep.

As you break in any new shoes, you may want to consider stocking up on these Blister BandAids. They are life savers in case you run into any blisters.

Most of these pairs of boots I’ve had for years. I take excellent care of my shoes but I also walk in them a lot living in New York. It’s why I invest in pairs and in brands that I know put quality first. So while the above may seem pricey, they have served me well and for much longer than when I buy less expensive boots.

Love my shoe collection? Shop My Bag Collection and My Favorite and Most-Worn Jeans.

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Reminder that you can shop My Closet for more style inspo.

You May Also Like:

• A Fall Capsule Wardrobe.
• My 2026 Fall Shopping Style Guide.
• Things from My Closet I Always Wear in Fall.

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