The 10 shoes below run from $68 Italian glove leather flats to premium calf hair booties, with most landing between $76 and $130.
The list below splits by what your day demands: a rubber-soled Mary Jane for the mile-plus walker, a pointed-toe block heel for the subway commute, a backless mule for the morning you are out the door in under a minute.
The burgundy penny loafer I keep coming back to starts there because it is the one pair I have found that handles coffee runs, client meetings, and dinner without a change.
1. Classic Leather Loafers
A pair of burgundy penny loafers with ribbed white socks and cuffed jeans is about as close to a uniform as I get in October.
The leather keeps its shape through years of wear, and the color goes with black, navy, or olive without any morning deliberation.
Black or brown works if burgundy feels like too much commitment. For the office, I look for a streamlined sole rather than the chunky lug versions that dominated last year; the slimmer shape tucks under straight-leg trousers without bunching.
Sarto by Franco Sarto’s Minerva line runs $130 in suede shades like camel and terra rosa, while Gap’s vegan suede version costs less if you are testing whether you will actually wear them daily.
Mine see coffee runs, client meetings, and dinners without a change. That is the test: one pair that handles three settings.
2. Ballet Flats
A thin buckled strap on a flat is what signals this year, not the color or the material. Designers finally added arch support and raised the topline so your foot sits in rather than spilling over the edge.
Quince’s Italian glove leather flat at $68 includes a cushioned insole and a heel pull tab; the topline sits higher than the old ballet flats I wore into the ground a decade ago.
Sam Edelman’s Alie Stud adds hardware if you want the shoe to do more of the outfit’s work.
Cognac or almond leather warms up fall neutrals better than black, in my view.
Check that the sole bends at the ball of the foot before you commit; a stiff flat is just a heelless pump with all the same problems.
A great autumn-ready pair, be they trendy sneakers or sleek ballet flats, can instantly make any chic outfit more interesting.
3. Mature Mary Janes
A single strap across the instep, no elastic, no mesh overlay: that is the Mary Jane I would actually wear.
That is the version worth trying this fall: the strap sits secure without the playground look of patent leather T-bars or the limp stretch bands that sold last summer.
A low block heel changes the shoe from costume into something you can wear with a midi skirt to work.
I would try them with cropped wool trousers and a thin sock in a contrasting color, or with a denim jacket and plaid skirt if that reads more like your closet.
PUMA’s sneaker-soled Mary Jane is an alternative if you walk more than a mile daily.
The hybrid keeps the strap detail but trades the heel for rubber. Decide based on your pavement, not your age.
4. Retro Sneakers
Brown suede with clean white stripes, no visible logo beyond the 3 lines: that is the silhouette that replaced bulky trainers this year. A low-to-the-ground sneaker slides under wide-leg jeans without the cuff stacking up awkwardly.
White, cream, and sage green are the colors I see most in this shape. Birkenstock’s Oswego and Josef Seibel’s Claire follow the same low-profile logic; the Josef Seibel runs narrower through the heel if you are between widths.
Pair them with a maxi skirt so the shoe stays quiet and lets the length do the work.
The minimal branding is the point. Let the line of the shoe read as a shape, not a billboard.
5. Clogs and Mules
Tan suede with a single buckle, backless, sitting on a white rug: the UGG D&K Sheepskin insole is visible, which tells you the comfort priority.
These are for mornings when you are out the door fast and still need to look like you decided.
Leather or suede both work; the wooden sole that is trending adds weight and a slight clatter that I find either satisfying or distracting depending on the floor.
Mules with a low block heel, like Lucky Brand’s Myrila at $76, pair better with bootcut jeans than flat versions because the heel keeps the hem from dragging.
Your toes stay covered; your heel does not.
That is the trade. Wear them with long pants and the gap matters less, or accept that some October days you will switch to a closed heel before dinner.
6. Platform Shoes
White platforms with "FASHION" printed on the side, cropped jeans, an anklet: the photo commits fully to the look.
I would leave the lettering and choose a plain leather or canvas upper in a color that does not shout, but the height and the block construction are worth keeping.
Two to three inches is the useful range.
Higher than that and the platform starts to wobble; lower and you might as well wear a standard sole. The chunky Chelsea boot version with a lug sole is an alternative if you need grip for wet sidewalks.
Block heels give you height with more stability than a stiletto, though any heel still shifts some pressure forward.
That is the mechanical fact that makes these wearable for a full day. Pair with wide-leg denim or a midi skirt so the proportion reads intentional, not like you stepped out in shoes from a different outfit.
7. Streamlined Heeled Booties
A pointed toe on a block heel is the compromise that actually works: the line reads sharp under trousers, but the heel width keeps you stable on subway grates and wet leaves.
J.Crew’s Stevie ankle boot in leopard calf hair comes in at a premium; Mango’s block heel leather version in burgundy gives you color for less if patterns are not your thing.
The key measurement is shaft height: too low and it gaps above the ankle bone, too high and it fights your jeans hem. A bootie that sits just above the ankle reads cleanest with slim pants or a skirt.
I would choose smooth leather in brown or burgundy over black; it softens faster and shows scuff less. Wear with straight-leg denim or a midi skirt with tights; the boot does the structure, the rest of the outfit stays simple.
8. Knee-High Boots
Knee-high boots are how I wear summer dresses into November without looking like I forgot the season. The boot replaces tights and most of the leg coverage; the dress stays the same.
Black leather with minimal hardware is the starting point; brown or deep burgundy are options once you know you will wear them weekly.
The shaft should hit just below the knee cap, not mid-calf, or the proportion cuts your leg in half. A riding boot cut, streamlined with small buckles, is the shape that reads current rather than costume.
Pair with a mini skirt and a tucked-in sweater, or over skinny jeans if the shaft is wide enough to zip.
They take longer to pull on than ankle boots, but one good pair means you are not rotating your whole closet when the temperature drops.
9. Leopard Print Shoes
Leopard print reads as a neutral in practice, not in theory. I treat mine like navy or cognac: they go with denim, olive, black, cream, and anything else I already own.
Start with a flat or a slingback if the pattern feels loud; the lower the heel, the less the shoe reads as a statement.
A pointed-toe slingback keeps the shape restrained so the print can do the talking and the cut can do the work. Mango’s block heel leather slingback in burgundy is $90, a useful comparison for construction quality at that price.
Snakeskin and zebra are alternatives if leopard feels expected, though I find snake harder to pair and zebra more limited in season.
Check that the print is printed leather or calf hair, not synthetic; the texture matters more than the pattern, and plastic-looking leopard is what turns the idea cheap.
10. Sleek Oxfords
I would wear the same shoe in all-black leather with charcoal or navy if I needed it to behave in a conservative office, but the two-tone version is the one I would choose for my own closet.
Platform oxfords with anti-skid soles are the variation if you walk more than a few blocks; the height adds presence without the instability of a heel, and the lug sole handles rain.
A review from a two-week trip to Southern Europe mentioned dry feet through two rainy days, which tells you the waterproofing on that pair.
Fitted trousers or a straight midi dress are the pairings that make sense; wide pants swallow the laces and the whole purpose of the shoe.
The polish is in the contrast between the tailored upper and whatever you wear below it.
How to Style These Trends
A leopard print flat against black trousers and a cream sweater reads intentional; the same flat with a patterned scarf and textured bag fights for attention.
Mix textures at the shoe itself rather than across the whole look. Suede clogs against denim, smooth leather loafers with ribbed wool socks, or calf hair booties with a cotton midi skirt give the eye one place to land.
Balance proportion from the ground up. A platform or chunky heel needs a wide-leg pant or full skirt so the silhouette reads as one shape.
A slim ballet flat or low-profile sneaker works with a cropped or straight leg where the ankle shows. The shoe and the hem should agree on how much space they take up.
Comfort and Versatility
The shoes that earn repeat wear are the ones that pass the three-setting test: coffee, work, dinner, no change needed.
A streamlined loafer or low block heel Mary Jane manages this because the structure holds up to scrutiny without demanding attention.
A stiff flat or a platform that sits too high turns into a problem by hour four, whatever it looked like in the morning.
The choice depends on your actual route, not an ideal one.
Color Trends
Burgundy is the fall color that acts like a neutral without being one.
Navy and deep olive function similarly: dark enough to anchor an outfit, colored enough to soften the harshness of all-black.
Earth tones like tan suede or terra rosa work best when the texture is visible; flat synthetic finishes turn camel cheap.
White and cream in leather or canvas stay relevant through fall if the shape is minimal and the branding quiet.
A true neutral, worn head to toe, lets a colored shoe become the single point of interest. The reverse, a colored outfit with a neutral shoe, is harder to pull off without the whole thing going flat.
Frequently Asked Questions
What shoe is trending for fall?
Loafers, knee-high boots, and retro sneakers are the shapes I see most this season. Mary Janes with a single strap and block heel, plus backless clogs with shearling insoles, also keep showing up in the styles worth trying.
What shoes are women wearing this autumn?
Women are choosing comfort that does not look like surrender. The common thread is construction details that do not photograph but show up in how long you stay on your feet.
What shoes to wear in October?
October is the month of switching, not committing fully to winter gear yet.
Brown suede or cream retro sneakers stay clean under wide-leg jeans without any cuff stacking, and backless mules last through most evenings until I need to change into something with a closed heel.
