Fall shoes this year swing between tall suede boots, refined pumps, preppy loafers, delicate ballet flats and retro sneakers, with buckles, animal print, burgundy and odd textures freshening up the familiar shapes. I always build an outfit from the shoe up, because the shoe decides the hem length, the trouser width and how far you can comfortably walk. So each look below starts with the footwear and then gives you the clothes, the proportions and the accessories that suit it. Pick the pair that fits your days, not the one that photographs best.
Try Boots On in the Afternoon, With Your Real Socks
Most of the shoe problems I see come from the fitting, not the shoe. A few habits make a big difference.
- Shop later in the day. Feet swell as the day goes on, so a shoe that fits at 10am can pinch by evening.
- Bring the socks or tights you'll actually wear. A boot that fits over sheer tights may be tight over a ribbed wool sock.
- For tall boots, measure the widest part of your calf while seated, since that's where a shaft feels tightest. Wide-calf and slim-calf versions exist for a reason.
- Walk on a hard floor, not just carpet. Heel slip and a loose slingback strap show up on tile.
- Leave a thumb's width of space in front of the longest toe for closed shoes, and a little more for pointed toes, which narrow sooner than they look.
If one foot is bigger, and for most people one is, fit the larger foot and add a thin insole to the other. And expect leather to need a little breaking in: a firm heel counter softens with wear, but a toe box that pinches on day one rarely stops pinching.
1. Suede Knee-High Boots With Midi Skirt
Suede knee-high boots bring the most texture for the least effort. Tuck a light knit into a flowing midi skirt, add fitted suede boots in chocolate, camel or taupe, and top with a tailored wool coat and a leather shoulder bag. The gap between hem and boot is where this look goes right or wrong: I want the skirt to end a few inches above the shaft or overlap it slightly, never a thin strip of leg at mid-calf. If you're petite, an almond toe and low stacked heel give you length. Sheer tights and small gold earrings keep it easy for daytime.
2. Over-the-Knee Boots With Sweater Dress
Over-the-knee boots turn a sweater dress into a cold-weather outfit. A relaxed ribbed dress at mid-thigh or just above the knee, sleek leather boots with a low heel, and only a sliver of leg showing between them. The common problem is the shaft slipping down as you walk; opaque tights grip better than bare skin, and a boot with a stretch panel or tie at the back stays up far better than a stiff one. A long tailored coat balances the short hem. Keep the colors linked, gray with black, cream with tan, burgundy with chocolate, and add a structured top-handle bag.
3. Kitten-Heel Pumps With Tailored Trousers
A kitten heel gives a pump's polish without the ache of a tall one, and it's what I recommend most for long office days. Wear pointed kitten heels in black, oxblood or cream with full-length tailored trousers, a silky blouse and a soft blazer. Hem length is everything: wide trousers should nearly touch the top of the shoe without dragging, while straight legs can stop at the ankle and show off the pump. Have trousers hemmed while wearing the actual shoe. A medium leather tote and a narrow belt in the shoe's color pull it together.
4. Ballet Flats With Straight-Leg Jeans
Ballet flats soften jeans instantly. Square or almond-toe flats with straight-leg denim, a fine cardigan and a fitted tee. Dark denim looks polished; faded denim feels like a weekend. Most flats have almost no arch support and a thin sole, so for a full day of walking I'd look for a pair with a cushioned insole or slip one in. Leather, suede, mesh or a quiet animal print, depending on how much detail you want. Jeans should finish near the ankle so the shoe shows. A cropped trench, a compact bag and ribbed socks on cool days.
5. Mary Jane Shoes With Pleated Midi Skirt
Mary Janes give a pleated midi a neat, preppy edge. Tuck a turtleneck or crewneck into a high-waisted skirt and add single-strap Mary Janes, flat or with a low block heel. The strap does more than look sweet; it keeps the shoe on your foot, which makes these one of the easiest low shoes to walk in. Burgundy, glossy black or deep red adds a seasonal accent. Sheer tights carry it into cooler weather, a cropped jacket marks the waist. Narrow pleats with a soft drape add less bulk than wide box pleats.
6. Chunky Loafers With Wide-Leg Pants
A thick-soled loafer is the right weight for wide-leg trousers; a dainty flat looks lost under all that fabric. Black or dark brown chunky loafers with pleated pants, a crisp shirt and a fitted knit vest. Let the trouser fall onto the shoe without hiding it. The lug sole also lifts you off wet pavement, which is why I reach for these in rainy weeks. New chunky loafers are stiff across the top of the foot, so wear them around the house with thick socks for a few evenings first. Ribbed socks in charcoal, cream or burgundy add color. A roomy tote and a long trench finish it.
7. Buckled Moto Boots With Denim Skirt
Buckled moto boots toughen up a denim skirt. Mid-calf black leather boots with a sturdy sole and one or two buckles, a dark denim midi, a fitted long-sleeve top and an oversized bomber or leather jacket. With bulky boots and a bulky jacket, the top must stay slim. The skirt should either clear the boot shaft or have a front slit, because a hem that hits right at the top of a mid-calf boot cuts the leg in half. Silver jewelry repeats the buckles, and a crossbody with minimal hardware keeps it clean. Add opaque tights and a soft scarf when it turns cold.
8. Western Boots With Floral Maxi Dress
Western boots ground a floral maxi and make it work for fall. Pointed or almond toes in brown, tan, black or weathered suede, with a long-sleeve dress in muted florals. If the maxi is very long, a low stacked heel keeps the hem off wet ground. A fitted denim or cropped suede jacket adds structure without hiding the dress. I'd stop at the boots: add a fringe bag, a hat and a big buckle and it tips into costume. Layered fine necklaces and a wide belt if you want a waist, and a leather crossbody.
9. Burgundy Shoes With Neutral Knitwear
Burgundy shoes are far more versatile than they look on the shelf. Loafers, pumps or ankle boots in deep burgundy, with cream trousers, a gray knit and a camel coat; the quiet palette lets the shoe stand out without looking like it came from another outfit. Repeat the color once in a small bag, belt or scarf, but don't match it exactly, since a close-but-off match looks like a mistake. Gold jewelry suits the warm red. For a casual day, swap the trousers for straight jeans and the shoes for burgundy flats; Mary Jane and ballet-flat shapes in rich red are among the easiest ways into this shade.
10. Animal-Print Flats With Black Jeans
Animal-print flats wake up black jeans more than any top could. Leopard, snake or zebra ballet flats in a plain shape, with black straight-leg jeans, a white shirt and a camel or dark brown blazer. Jeans ending at the ankle show the print properly. Printed calf hair, a common finish on these flats, wears bald where your feet rub together, so I'd save that version for less walking-heavy days. Muted brown, cream and black prints are the gentlest way in; they behave almost like a neutral. A black leather shoulder bag, small gold hoops and a watch.
11. Retro Sneakers With Satin Midi Skirt
Retro sneakers take the formality out of a satin midi skirt. Low-profile sneakers in cream, navy, green or burgundy, a bias-cut skirt and a relaxed crewneck. A slightly oversized leather or denim jacket bridges sporty and silky. Satin is slippery, so tuck the sweater only at the front or it'll keep creeping out. Keep socks low or choose a neat ribbed pair in the sweater's color. The skirt should land between mid-calf and ankle so the slim sneaker shows. It's a good way to wear a dressy skirt on an ordinary day.
12. Mesh Ballet Flats With Cargo Pants
Mesh flats are a September shoe, honestly. They're airy and pretty, but they let in cold and rain, so I treat them as an early-fall and indoor pair. Wear them with relaxed cargo pants, a fitted ribbed top and a cropped utility jacket; the delicate shoe stops the cargos looking rugged. Black mesh is the most versatile, a crystal-detailed pair the most decorative. Cargos need to taper or cinch near the ankle so they don't swallow the flat. A sleek shoulder bag, sunglasses, small earrings.
13. Pointed Slingbacks With Pencil Skirt
Pointed slingbacks give a pencil skirt a sharp finish and feel lighter than a closed pump. Knee-length or midi skirt, a soft blouse, a fitted blazer. A short kitten heel gives lift without the strain of a stiletto. Black, chocolate, cream or burgundy all suit fall tailoring. The strap is the fit test: it should sit snugly above the heel bone and not slide down as you walk, and an elastic insert in the strap helps. Sheer tights close to the shoe's tone keep the leg line unbroken. A structured work bag and slim belt.
14. Slouchy Boots With Knit Mini Dress
Slouchy boots are the relaxed cousin of a sharp knee-high. Soft leather or suede boots with a long-sleeve knit mini dress and an oversized wool coat. The loose shaft gives texture while the plain dress keeps it from looking bulky. On slim calves, slouch looks deliberate; on fuller calves, a very slouchy shaft can pile up, so I'd pick one with gentle rather than heavy rouching. Low block heel for every day, slim heel for evenings. Opaque tights connect dark boots to the short hem. A knit tunic over leggings works for more coverage.
15. Embellished Heels With Trouser Suit
Embellished heels turn a plain trouser suit into an event outfit. A single-breasted blazer and straight or wide pants in black, navy, charcoal or deep brown, with a silk camisole or simple fitted top. Crystal pumps, feather-trimmed heels or sculptural hardware become the focal point, so the bag stays small and plain. Let the trouser hem show at least the front of the shoe, otherwise the detail you chose disappears. Crystal trims snag on the opposite ankle and on fine tights, so I check where the stones sit before buying. Polished earrings and clean hair finish it, and it's a smart alternative to a dress.
Puddles, Road Salt and the Shoes on This List
Fall weather is hard on shoes, and each material on this list reacts differently. Here's how I handle them.
Suede and nubuck
Spray new suede with a protector before the first wear and again every few weeks. If it gets soaked, stuff it with paper and let it dry at room temperature, never on a radiator, then brush the nap back up. A suede eraser lifts most scuffs and light salt marks.
Smooth leather
White salt lines come off with a cloth dampened in a mix of water and a little white vinegar, followed by conditioner once dry. Give leather shoes a day off between wears so moisture from your feet can dry out; cedar shoe trees help them keep their shape.
Mesh, satin and embellished pairs
These don't really recover from a soaking. Check the forecast, carry them in a bag to an event, and keep a plainer pair on your feet for the walk there.
Start With the Pair Your Week Needs Most
A good fall shoe sets the proportions and the polish of everything above it. This season has dependable classics alongside bolder ones: suede boots, delicate flats, retro sneakers, buckled moto boots and embellished heels. You don't need all of them. Pick the one shape that suits your routine, build outfits from its color and shape, and get the hems right. If I had to start a fall shoe wardrobe with one pair, it would be a dark chunky loafer: it handles rain, trousers, jeans and skirts, and it lasts for years with a little care.
Related posts:
