If you’re looking to build out your shoe collection with shoes that are stylish, practical and will fit most any scenario for the seasons ahead, look no further than today’s post!

Today I am breaking down my favorite shoes to wear for Fall & Winter. Over the years I have spent time amassing a wardrobe of quality shoes that are comfort and able to be worn in versatile ways. If you’re interested in my entire collection be sure to read my My Favorite and Most Worn Shoes + How I Take Care of Them post.

The Best Shoes for Fall & Winter

Classic, Go-with Everything Sneakers

By now you all know I love these sneakers and have worn them an almost embarrassing amount of times since getting them to wear on my trip to Copenhagen and Stockholm years ago. I now bring them on pretty much every trip since they are so versatile. A head’s 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 loafers 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. 

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.

Code WITWHIMSY15 for 15% off your first Freda order!

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 and just bought in another color.

This Veja sneaker comes in a variety of color ways.

Adidas Sambas

I’ve amassed a small collection of Sambas. This sporty sneaker is great with a jean or a trouser and so comfy.

Black 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.

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 and this are more affordable options.

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 silhoutte, theses suede mules (size down half a size if in between sizes) are excellent.

You can use code MEGHAN15SPRING25 for 15% off your purchase of Inez shoes.

T Heel Boots

The Staud Wally boots I got last Winter I wear so much thanks to being so comfortable.

They have a variety of styles and colors of the silhouette for this year and even a knee high version I am eyeing.

The Chic Sock Bootie

These booties were the best pair of shoes I bought in 2017 and they still get as much wear from me five 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. 

A similar look for less from Marc Fisher HERE.

Classic Loafers

The good reviews on these Sam Edelman loafers made them a new addition to my wardrobe a few Fall seasons ago and I can confirm they are in fact very comfortable and really well made. I took my usual size 7.

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

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.

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 and have blogged about this great shoe here, here & here.

The Suede Ballerina 

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

The Comfy, Sporty Sneaker

These APL Techloom sneakers were a best buy of 2019 and I haven’t stopped loving wearing them. They are so comfortable and I love that I don’t have to wear socks with them. (I sized half a size down to a 6.5 as a result).

They are the shoe I reach for every time I am heading out for a long walk, going on a light hike or want to be extra comfortable in a sneaker that doesn’t sacrifice style. In addition, they are my favorite casual, be active sneaker. 

The Heeled Bootie

These heeled Marc Fisher boots are so good for Fall and Winter that I now own them in two colors. The heel is the perfect height and they go with pretty much my entire wardrobe for these seasons. I love the different materials and colors they come in, too! 

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 Chic Winter Boot

My favorite boots for Winter, these Marc Fisher Izzie boots are as stylish as Winter boots come. They are warm, so chic and crazy comfortable. They sell out every single season for good reason (I’ve already seen them sell out once this season!) I just bought them in the suede version as I know I’ll wear those a lot, too (see below!) Original post here.

The Stylish Sock Bootie

These Inez booties are so comfortable and I love the perfect neutral color of them in the Ginger Suede. A full review can be found here. I wore the Ginger so much since I got them back in 2019 that I bought the Black last year and plan to buy the Rye this year.

You can use code MEGHAN15SPRING25 for 15% off your purchase of Inez shoes.

The Shaft Boot

A stylish vintage boot perfect for pairing with skirts and dresses – meet the Inez Mila Boot.

You can use code MEGHAN15SPRING25 for 15% off your purchase of Inez shoes.

The trendy, sporty sneaker

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. This year they’ve been my go-to when heading out the door in my favorite joggers. 

The Chelsea Boot

These Boss Boots are comfortable enough for loads of miles but also stylish to go with most of your Fall & Winter outfits. Better yet? They hold up in rain and light snow, too. 

This style is no longer available but there are loads of similar styles sold like this pair and this pair from reliable brands.

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!

Knee High Suede Boots

The Sarah Flint Alexandra Boot have a low tortoise heel that’s as striking as it is practical so you can really trot in these boots. They’re slim to the leg making them very flattering and have a hidden zipper so the boot doesn’t get bulky.

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

Suede Knee Hight 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, I also own and love the J.Crew Stevie boots. So good for walking around.

I got so much wear out of mine from last year and can’t wait to pull them out again.

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-MEGHAN 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.

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.

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 WITWHIMSY15 for 15% off your first Freda order!

This pair by Sam Edelman are equally great but definitely heavier and therefore I won’t travel with them usually. They are also water proof though and work well as a stylish yet weather-friendly shoe in colder months.

The Casual Knee High Boot

I wanted to add a chic, yet casual low heeled boot to my favorite boots this season and these Sezane Adele Boots fit the bill. They are beautifully made, comfortable to walk in and have a looser calf shaft so I didn’t have to have them adjusted at all.

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.

I took a half size down to a 36.5 as that’s all they had (they sell out regularly – it took me a year of waiting to have these restocked till I got them!) and they fit perfectly. I could have probably done a 37, too however.

Toteme has a similar looking pair.

The Riding Boot

These Sarah Flint Perfect Riding Boot 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.

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

. . .

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:

• My Favorite Sweaters.
• Casual Fall Outfit Ideas With Jeans.
• A Roundup of My Favorite Boots and Booties.

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