I notice fall has really started when I stop grabbing sandals without thinking. One morning, I’ll pull on loafers or ankle boots, which always feels like turning a page. The mornings are cooler, the leaves look a little tired, and somehow every outfit looks better once you’ve got something substantial on your feet.
When I’m building my seasonal rotation, I’m not hunting for whatever’s trending in my feed. I’m pulling pieces that will still feel right next year, and the year after. The pairs that look as good with denim as they do with a dress, that don’t pinch by midday, and that make me stand a little straighter when I walk.
Here’s my list of fall shoes for women that I keep coming back to, the classics worth making space for in your wardrobe.
1. Leather loafers
A well-made leather loafer is the kind of shoe that bridges summer and winter without any awkwardness. I wear mine with cropped trousers to the office and with straight-leg jeans on weekends. Go for a rich brown or black for the most wear, and look for a sole with just enough cushioning so you can actually walk all day.
If you love the old money aesthetic, loafers are a quiet nod to it. Pair them with a wool blazer and you’re halfway to a business casual outfit without even trying.
Shop here: Velasca, Margaux, Bass Weejuns
2. Chelsea boots
The beauty of Chelsea boots is how easy they are. No laces, no fuss, you just pull them on and go. A black leather pair will see you through almost anything, but I also love a dark brown suede version for days when I’m feeling a little softer in my styling.
They work with slim jeans, but I also like them with a lighter dress since the boots keep it from looking too summery. The ankle height matters more than you’d think. For me, just above the bone always seems to look best.
Shop here: Chelsea Boots Collection
3. Ballet flats
Most people pack away their flats when the weather turns, but I wear mine until it’s truly cold. They smarten up jeans and make a formal outfit feel a little softer. I usually go for leather or suede in camel, taupe or navy so they work with my old money color palette closet without me having to think about it.
On colder mornings, I’ll add fine-knit socks in the same color. It feels simple and a little French.
Shop here: Charles Keith, Sam Edelman
4. Heeled ankle boots
If I need fall shoes that look nice but still comfy, I go for my block-heeled ankle boots. I’ve worn them to dinner, to work, and even on weekends, and they never feel out of place… they always seem to work.
I try to stay around two inches because anything higher ends up impractical. Leather ages beautifully, but suede has that softer, dressier feel that makes even jeans look special.
5. Riding boots
Every few years, I bring my tall leather riding boots back from storage and wonder why I ever put them away. They’re elegant in a way no other boot is, especially in deep brown leather with minimal hardware.
I love to wear them with slim trousers or a wool midi skirt. The rest of the outfit can be simple… maybe add a cashmere sweater, a classic coat, and the boots feel like the main character without much effort.
You can also shop here: Ariat, Aeyde, Dover Saddlery
6. Brogues or oxfords
Not everyone thinks of brogues when fall comes around, but I always find myself pulling them out. They add a bit of sharpness to softer outfits and somehow make me feel more put together. On the days when sneakers look too relaxed and heels feel like overkill, these end up being the pair I grab.
I like patent leather in autumn because it can take a wet sidewalk without looking ruined, which makes them easy for everyday wear.
Shop here: Crockett & Jones, Sezane
7. Suede ankle boots
Yes, suede boots are high maintenance and take more effort, but I still keep a pair around every fall. The lighter shades, beige, grey, even a soft taupe, somehow make outfits look thought out without much trying. They do need a spray with protective coating before you wear them outside, so they won’t get ruined in the rain… I learned that the hard way.
I like them best with midi dresses or a long coat, where just the tip of the boot shows. It feels subtle, but people always notice.
8. Sneakers (but make them clean)
I’m not talking about gym shoes. I mean a clean, minimal leather sneaker in white, cream, or even a soft blush. These are the pairs you wear with trousers and blazers, or with dresses when you need to walk a lot but still look like yourself.
If you keep them spotless, they work surprisingly well with the clothing storage habits that help extend a shoe’s life.
Try: Veja Esplar, Adidas Samba OG or Superga
9. Kitten heels
A small heel can make more of a difference than you think. I keep a pair of kitten heels in rotation every fall, and I end up wearing them more than I expect. They’re not dramatic, but they change the way clothes sit. They add a bit of height… just enough that I notice. I’ll wear them with cropped jeans, especially if I don’t want to think too hard. Other times it’s a pleated skirt, just because it feels right that day.
On colder days, I’ll pull them out with tights and even shorts, which sounds odd but always works. The pointed toe helps the leg look longer, and in autumn, I’m drawn to black patent or a deep burgundy leather. Both feel classic without trying too hard.
Shop here: Charles & Keith, Mango
10. Waterproof boots (that don’t look it)
It took me years to find rain boots that didn’t ruin an outfit. Now, I won’t go through fall without them. Look for styles in matte black or dark olive, with minimal branding and a sleeker shape than the usual chunky wellie.
Pair them with a trench coat and you’ve turned a dreary weather day into an excuse to look pulled together.
Shop here: Nordstrom
How to choose your fall shoes wisely
Fall is a tricky season, warm one day, cold the next, so you want fall shoes that can shift with the weather and still work with whatever I’m wearing. A few things I think about:
- Color palette: I lean on neutrals in autumn, browns, navy, black, because they go with everything.
- Material: Leather and suede always look better over time, as long as you take care of them.
- Comfort: I usually ask myself if I could walk a good ten blocks without thinking about my feet. If not, they stay on the shelf.
- Care habits: A bit of attention goes a long way. I’ll slip in shoe trees, brush off any dirt, and give them a quick polish before putting them away for winter.
Fall shoes aren’t just there for the weather. They set the mood. Some mornings, jeans and a sweater feel complete once I’ve got the right pair on. Other times, the shoes are off and the whole outfit falls flat. I’ve had mornings where I liked my coat and felt fine about the rest, but the shoes threw it off. It’s strange how they can shift the whole mood, even how you walk.
If you invest in the classics, choose boots, flats, and sneakers that are a little more refined. You’ll find yourself wearing them year after year. By the time fall comes around again, they feel familiar in the best way.
