The Best Shoes to Own for Fall & Winter

Easy Fall Outfit I wit & whimsy
After the popularity of sharing my favorite and most worn jeans recently, I thought I’d do the same for my shoes! I am a shoe gal through and through. They can truly make an outfit and as a New Yorker I put my shoes to work so I’m also sharing in this post how I take care of my shoes + protect them.

The Best Shoes for Fall & Winter

Classic, Go-with Everything Sneakers

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. I now bring them on pretty much every trip since they are so versatile. (And I wore them a lot with dresses while in Lisbon!) 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.
Plaid Blazer + Gucci Loafers I wit & whimsy

Gucci Loafers

These Gucci loafers are an iconic shoe you won’t regret. I wear these once a week 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.
Veja Esplar Logo Sneakers I wit & whimsy

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.
Styling Classics I wit & whimsy

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! I wear them year round but particularly love them with Fall sweaters. 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, Sam Edelman makes a similar pair. Original post here.
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. 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. I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week. Original post here.
Sezane Gaspard Sweater 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 a big life change. 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 also own them in black. Original post here.
Leather trimmed coat on Meghan Donovan of wit & whimsy

Over The Knee Boots

Ever since getting these boots in 2014 I have worn them non-stop through Fall & Winter. They also are great to travel with because they collapse down easily. The quality and comfort makes them worth the splurge. They stay up over the knee (a lot of inexpensive brands will constantly slouch down taking away from the elongating illusion over the knee boots are good for) and they’re great over jeans or with dresses. Original post here.
French Girl Style Striped Tee I wit & whimsy
The good reviews on these Sam Edelman loafers made them a new addition to my wardrobe this season and I can confirm they are in fact very comfortable and really well made.
Vince Coat I My Favorite and Most Worn Shoes

Errand Sneakers

On weekends I live in these sneakers. They’re more stylish than a pair of Vans, they’re super comfortable and they’re great with jeans or, let’s be honest, leggings. They’re my go-to for going to/from my workouts and running errands in my neighborhood.  I wear them so much they are almost always in my foyer instead of my closet. Original post here.
Casual Fall Neutrals I wit & whimsy

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. Original post here.
Sarah Flint Perfect Zip Bootie I wit & whimsy

Booties with Detail

And if you like an even lower heel and some detail, check out the Sarah Flint Perfect Bootie. Original post here.
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.
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. 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. They are my favorite casual, be active sneaker. Original post here.
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! Original post here.
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. Original post here.
Cute Cardigans for Fall 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.
Plaid Blazer + Distressed Denim I wit & whimsy

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.
Everlane Denim Guide

The Boots Made for Walking

These Boss Boots are one of my top sellers. They’re 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.


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