The Best Shoes to Own for Fall & Winter

October 17, 2023

Cafe Pigalle Paris Khaite Sneakers J.Crew Trousers Fall Outfit

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

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.

Plaid Blazer + Gucci Loafers I The Best Shoes for Fall & Winter

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. Original post here.

Gucci Loafer

Classic Gucci Loafers

Striped Sweater from Bash Paris, Senreve Bag, MMLafleur Pants, Veja Sneakers

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. This Veja sneaker comes in a variety of color ways.

Nike Daybreak Sneakers

Another casual style I own and love with a more vintage vibe is the Nike Daybreak Sneaker. I size down a half size in Nikes.

The Best Shoes for Fall & Winter

Chanel Heeled Slingbacks

Every year for my birthday I buy myself a gift and a few years ago 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 just as easily as they can 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

Chanel Slingbacks

Chanel Flat Slingbacks

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

Teddy Coat and Kick Flares on Meghan Donovan of wit & whimsy 3

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. 

Black Converse in Paris Outfit

Black Converse

Sneakers with a bit of an edge – enter the black Converse. I reach for these in Fall & Winter to wear with all my neutrals. The perfect cool French girl inspired sneaker.

The Best Shoes for Fall & Winter French Girl Style Striped Tee I wit & whimsy

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!

Casual Fall Neutrals I The Best Shoes for Fall & Winter

Comfortable Suede Booties

A thoughtful heel height and careful construction of these Margaux suede boots make them great for walking around. I’ve worn them with jeans and with skirts for Fall & Winter. They come in three shades. 

Margaux Downtown Boot

If you prefer a pointed toe, the Margaux Downtown Boot is perfect for you.

Sarah Flint Natalie Bow Flat in Nude I wit & whimsy

The perfect 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.

Fall Outfit featuring Veronica Beard Blazer, Agolde Straight Leg Jeans, Manolo Blahnik Ballerina Flats

The suede ballerina flat

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

Weekend Casual Athleisure Outfit I wit & whimsy

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. 

Barbour Icons Collection I 125th Anniversary I wit & whimsy

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! O

A Guide to the best of the Vail Valley I wit & whimsy

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.

Marc Fisher Izzie Snow Boots

Inez Boot Review I wit & whimsy

The Stylish Sock Bootie

These Inez booties are so comfortable and I love the perfect neutral color of them. A full review can be found here. Original post here

You can use code WHIMSY15 for 15% off your purchase of Inez shoes.

Celine Box Bag

I have the higher heel version also seen above. But I don’t wear them as much as the lower heel style.

Use code WITWHIMSY15 for 15% off.

Inez Mila Boot Fall Outfit

The Shaft Boot

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

You can use code WHIMSY15 for 15% off your purchase of Inez shoes.

Plaid Blazer + Distressed Denim I The Best Shoes for Fall & Winter

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. Original post here.

I also have this colorway which I love particularly in the Fall.

Everlane Denim Guide

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 another favorite brand of mine.

Rag & Bone Rover Boots

The Comfortable Suede Bootie

This timeless style of bootie is so versatile and I think investing in a pair comfortable enough to walk all over town in is so worthwhile. (So many less expensive styles exist but they are painful!) These Rag & Bone boots are my favorites. They go well with jeans as well as skirts and dresses in the Fall. Other colors are available, too.

M.M.LaFleur O'Hara Blazer Review Fall Outfit

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.

& Other Stories Coat and Sarah Flint Pumps with Celine Bag

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. 

Knee High Suede Boots

The Sarah Flint Alexandra Boots are so perfect for a walkable boot you want to wear with dresses and skirts.

Plaid Blazer Tweed Fall Outfit in Paris

The Leather Knee High Heeled Boot

Similar in style – 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.

Dress Boot

Every girl’s closet needs a pair – the perfect dress bootie to wear all Fall & Winter. This pair is so sleek and yet comfortable.

Mule Kitten Heel

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

A Tour of The Ritz Paris I wit & whimsy

Chanel Ballet Flats

These Chanel ballet flats were another investment pair of shoes I thought about for a long time before I actually bought them in 2016. I treasure these shoes and the sentiment they hold as I bought them while in Paris just before I started my self employment journey. They remind me of a time where I was full of hope and excitement and they always remind me of one of my most special trips to Paris.

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.

Freda Salvador Boot Fall Outfit

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.

Aqua Puffer Jacket and Sam Edelman Lug Sole Boots

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.

Jenni Kayne Mules

The Shearling Mule

Certainly not my most versatile shoe and definitely more novel but I love that this is a pair of shoes with personality and great for throwing on around the neighborhood.

Sezane Fall Boots

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

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.

Khaite Riding Boot

The Riding Boot

I looked for what felt like years to find the perfect riding boot. I wanted something unbranded (read: no logos!), something that felt really timeless, was comfortable and was slim. When I saw these Khaite Riding Boots I loved them but not at their price point. But by some stroke of luck and a tip from a friend, they were briefly marked down on Saks during one of their sales and I scored them for over 40% off. 

I took my usual size 37 in these and I did have to bring them to my cobbler to have the shafts stretched as I found them rather narrow.

A good look for less I recently spotted is this pair from & Other Stories.

. . .

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.

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

. . .
Shop the Post



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

You May Also Like:

This post contains affiliate links. Should you purchase something from an affiliate link, I may earn commission, at no cost to you. Thank you for your support of my work!

comments +

  1. This is such a solid list of must-have shoes for the colder season. I will definitely keep it in mind for future shoe purchases to complement what I already have. Plus, love that all the shoes you mentioned are super versatile and be worn with so many outfits!

Leave a Reply

Your email address will not be published. Required fields are marked *