Best Fall Shoes for Women: Timeless Styles I Wear Every Fall

I don’t have a different pair of shoes for every outfit. Instead, I rely on a handful of styles that work with everything in my closet. Once the weather starts to cool, I find myself reaching for loafers, ballet flats, ankle boots, and knee-high boots on repeat. If you’re wondering which are the best fall shoes for women, I’m sharing the styles I actually wear, why they’ve earned a place in my wardrobe, and how I style them throughout the season.

If you’re in a hurry, these are the shoes I wear most each fall:

• Loafers for everyday outfits
• Ballet flats for dresses and jeans
• Ankle boots for nearly everything
• Knee-high boots with dresses and skirts
• Pumps for weddings, dinners, and special occasions

My Favorite Fall Shoes

Best Fall Loafers

Loafers are the first shoes I switch to once sandal season is over. I wear them with straight-leg jeans, wide-leg jeans, pants, and even joggers when I want to look a little more polished. If I could only recommend one everyday fall shoe, this would probably be it. They’re that perfect in-between shoe when sneakers feel too casual but ballet flats don’t quite feel right.

Because I wear loafers so often, I’ve found that different styles serve different purposes. Here’s how I think about each one when I’m getting dressed.

Suede Loafers

I reach for my suede loafers when I want my outfit to feel casual. I like suede loafers because they soften an outfit in a way polished leather doesn’t. The matte texture feels more relaxed and easy to wear every day, and it pairs really well with denim, chinos, and corduroy. The pair I reach for most are the Felize. They are a classic driving loafer that makes them perfect for wearing everyday. If you’re considering them, I share more about the fit, comfort, and how they compare to the Una Loafer in my M.Gemi review. I recommend taking a half size up in these. If you’re new to suede shoes, I also share my favorite tips for cleaning and caring for suede so they’ll last for years.

Classic Leather Loafers

When you want a truly timeless shoe that you can wear with casual or dressier outfits, a classic leather shoe like these ballet loafers, are what I reach for. I have these loafers in four colors because they are that good. And they look much better in person then they do online. I get asked about mine just about every time I wear them.

If you like a slightly more classic look, horsebit loafers are another timeless option. I own a pair myself and find they dress up jeans beautifully. Especially if you want to add something interesting to your outfit, the horsebit hardware is so charming for fall. If you’re looking for outfit inspiration, you can also read my guide on how to style loafers.

Sleek Loafers

For a sleeker version that can also go from day to night, I love these loafers with the elongated toe. They look especially pretty with wider leg pants and jean because the slim profile balances out the wide leg. There is no hardware on these, so there’s no competing with belts or any hardware on your bags. I choose these over my ballet loafers when I want a more polished, minimal look.

In general, if I want something more relaxed, I reach for my suede Felize loafers. If I’m wearing wide-leg jeans or want a slightly dressier look, I usually choose the sleeker Una loafers instead. The ballet loafers are the in-between, and can be worn casually or a bit dressier. For any of the M.Gemi shoes I mention, you can save 15% with TARA15.

Best Ballet Flats

Ballet flats are the shoes I reach for when I want something feminine but still comfortable enough to wear all day. They work just as well with jeans as they do with dresses or pants, making them really versatile. Whether you prefer a classic round toe or a more modern pointed toe or squared toe, they’re a style I wear throughout the year, but especially in the fall. Depending on the outfit, I find myself reaching for different styles for slightly different reasons.

Classic Ballet Flats

Some outfits just call for something simple and classic. A classic ballet flat works with everything from denim to dresses. I reach for mine when I want something understated that goes with almost anything in my closet. I love this pair that reminds me of a classic Chanel flat.

Mary Janes

Although these have a strap, I wear them exactly like I would a classic ballet flat. In fact, if I could only buy one pair of ballet flats, I’d choose the Mary Janes every time. I love the added support of the strap because I don’t have to worry about slipping out of them while I’m walking. These flats have become one of my most-worn pairs because they’re comfortable enough for all-day wear while still feeling feminine. I wear them three seasons out of the year and own them in leather, woven leather, and suede. I especially love how they look with dresses.

Ballet Slippers

If you want something that feels a little more elegant, this style is a beautiful option. Inspired by traditional ballet shoes, the crossover straps make them feel a little more special than a classic ballet flat. I like wearing them with wide-leg pants and dresses when I want my shoes to feel like more of a feature. They are incredibly soft and comfortable too. I have the navy pair and what I love about them is that they blend seamlessly into jeans. Sometimes I don’t want to add another color into my outfit, I just want it simple, and these help do just that.

If you wear flats as often as I do, you might also enjoy my guide to the best jeans to wear with flats, where I share the denim styles I reach for most with ballet flats, loafers, and Mary Janes.

Best Fall Ankle Boots

Ankle boots are usually the first boots I pull out every fall. They’re one of the easiest shoes to wear with jeans, dresses, skirts, and pants, and I probably wear them more than any other boot. Over the years, I’ve found myself reaching for different pairs depending on what I’m wearing.

My Everyday Ankle Boots

Margaux Downtown

Best everyday ankle boot. On any given fall or winter day, the Dowtown boots are usually the ones I reach for. I own them in black leather, brown leather, and brown suede. They’re the pair I wear most often because they work with almost everything in my closet. Plus the 5mm of foam padding makes them really comfortable. I also really love the slightly pointed toe that works with both wide-leg and straight leg jeans and pant styles. They are extremely versatile.

If I could only own one pair of ankle boots, these would be it. They’re easily my most-worn boots because they work with both straight-leg and wide-leg jeans, dresses, and skirts. They can look dressy or casual, all depending on your outfit.

Best for Straight-Leg Jeans

Sarah Flint Perfect Zip Bootie

These are the most elegant boots I own. When I want my outfit to feel a little more polished, this is usually the pair I reach for. I own them in the 70mm and the 30mm heel height, in black and saddle. The rounded toe feels a little more casual, and looks great with straighter silhouettes like straight-leg jeans and pants. The nice block heel works especially well with my longer jeans when I need a little lift (I’m 5’2″). I show how I wear them with skirts too further down in this post.

Best for Wide-Leg Jeans and Pants

Inez Paz

These are my favorite for wide-leg jeans in fall. When I’m wearing wide-leg jeans or pants, I almost always reach for a tapered toe because it peeks out just enough beneath the hem and creates a longer line. The Paz is my favorite boot for this. I own it in both black and burgundy, and the slightly taller heel gives me just enough extra height for my longer jeans while still being comfortable enough to wear all day.

Dressier Ankle Boots

If I’m dressing up for dinner or a night out, I still love a sleek pointed-toe ankle boot like the Inez Valentina. It isn’t always available because Inez tends to restock it seasonally, but it’s a beautiful example of a dressier ankle boot if you happen to find it. As an alternative, these boots are just as beautiful with a slightly lower heel.

Knee-High Boots

Knee-high boots don’t get as much wear in my closet as ankle boots simply because I wear so many straight-leg and wide-leg jeans throughout the fall. But when I’m wearing a skirt or dress, they’re almost always the first shoes I reach for. Especially when I wear sweater dresses. They not only help keep your legs warm, but they are my favorite way to wear skirts and dresses in the cooler weather. And so much more stylish too.

When I’m shopping for knee-high boots, I pay close attention to shaft height and calf circumference because those two measurements make the biggest difference in how they fit. A pair that’s too tall or too wide won’t get nearly as much wear, no matter how beautiful they are.

Sneakers

Even though loafers and boots take over my wardrobe in the fall, I still wear sneakers a few days a week. I tend to gravitate toward classic sneakers in neutral colors because they pair just as easily with denim as they do with casual dresses. A few of my favorites are the Tretorn and the Adidas Samba. They’re comfortable enough for long walks with my dog, but still look polished enough that I don’t feel like I have to change my shoes to run errands or meet a friend for coffee.

Pumps

I don’t wear pumps as often as I used to, but there are still occasions when they’re the right choice. If I’m heading to dinner, a special event, or want to dress up a pair of jeans, I still reach for a classic pump or slingback. Rather than owning lots of different styles, I prefer a few timeless pairs that I know are comfortable enough to wear for several hours. In the fall, I almost always gravitate toward chocolate brown suede.

Classic Pumps

A classic pump is still the heel I reach for most often. I wear them with dresses for weddings and holiday parties, but I also love pairing them with jeans and a blazer when I want a more polished look. If you’re only going to own one pair of heels, this is the style I’d recommend because you’ll get the most wear out of them.

Slingbacks

Slingbacks are the pair I reach for when I want my shoes to feel a little less formal than a classic pump. They’re beautiful with dresses and cropped pants and are an easy way to dress up an outfit without feeling overdressed.

Best Fall Shoes to Wear with Dresses and Skirts

For Everyday Dresses

Ballet flats are usually my first choice for casual shirt dresses and skirts when the weather is still mild. They feel pulled together without looking overdressed, and are comfortable enough to wear all day. I tend to reach for a classic ballet flat or a Mary Jane style depending on the outfit.

For Casual Fall Outfits

If I’m wearing a midi dress or skirt and want the outfit to feel a little more relaxed, I’ll usually choose ankle boots. I like that a little bit of leg shows when I walk because it keeps the outfit from feeling too heavy. This is one of my favorite combinations for everyday fall outfits.

For Cooler Days

Once the weather gets colder, knee-high boots, or calf-height, become my first choice with dresses and skirts. I love the long line they create, and they’re an easy way to stay warm without giving up dresses once summer is over. They’re especially beautiful with sweater dresses and midi lengths.

If you wear dresses and skirts throughout the fall, you’ll also find plenty of outfit inspiration in my guide to the best boots to wear with dresses.

For Dressier Occasions

If I’m heading to dinner, a wedding, or another dressier event, I’ll usually reach for a classic pump or slingback. They instantly elevate a dress while still feeling timeless enough to wear year after year.

Best Fall Shoes for Women FAQ

What shoes are in style for fall?

Timeless styles like loafers, ballet flats, ankle boots, and knee-high boots continue to be some of the best fall shoes for women because they’re timeless, and easy to wear year after year. This season, I’m also seeing rich chocolate brown, deep burgundy, and elegant two-tone shoes everywhere. Rather than buying something completely new every year, though, I prefer investing in classic styles I know I’ll wear season after season.

What shoes do you wear with dresses in the fall?

It depends on the style of dress and the weather. For sweater dresses and midi dresses, I usually wear knee-high boots. For warmer fall days, I reach for ballet flats or Mary Jane flats. If I’m dressing up for dinner or an event, a classic pump or slingback is usually my first choice. For casual midi dresses, ankle boots are another favorite because they keep the outfit feeling relaxed.

Are loafers still in style?

Absolutely. Loafers have become one of the most versatile shoes in my wardrobe and are one of the first pairs I start wearing once sandal season ends. Rather than focusing on trends, I recommend choosing a timeless leather or suede loafer that you’ll continue reaching for year after year.

What color shoes are best for fall?

I get the most wear out of black, chocolate brown, cognac, and taupe because they work with almost everything in my closet. If you already have those basics covered, burgundy is a beautiful way to add color while still feeling timeless.

What are the best comfortable fall shoes?

If comfort is your priority, I’d start with loafers. They’re the shoes I wear most because they’re just as easy to wear as sneakers but look a little more polished. Ballet flats are another great option for everyday wear, while ankle boots become my go-to once the weather gets colder.

How many pairs of shoes do I really need for fall?

You don’t need a different pair of shoes for every outfit. Most of my fall wardrobe revolves around a handful of styles that work with almost everything I own. If you’re starting from scratch, I’d begin with a great loafer and an everyday ankle boot. Those are easily the two styles I wear most each fall.

Building a collection of fall shoes doesn’t happen all at once. Mine has grown over the years, one pair at a time, based on what I actually wore. Start with the styles you’ll reach for most often, then build from there. That’s exactly how I’ve built my own collection over the years. You’ll get far more wear from a handful of thoughtfully chosen shoes than a closet full of pairs you rarely reach for.