top 10 shoes for fall and winter | the sunday brief

it’s full steam ahead into fall which means we’re trading in our flip-flops and sandals for loafers, boots, and booties. today, i’ve put together a list of my top 10 shoes for fall and winter.

ballet flats

ballet flats always make my top 10 shoes for fall and winter list. these shoes have been in constant rotation since i was a teenager. back then i wore ballet flats with tights, skirt, and a sweater for an east coast preppy vibe. a ballet flat is my go-to shoe for skirts or jeans. or for those days when i know, i’ll log in more than one mile. this pair by Tory Burch travels with ease as it folds in half and tucks into your suitcase without taking too much space.

ballet flats here, here, and here.

loafer

what can i say about the mighty loafer except it goes with so many outfits? straight leg jeans, skinny jeans, skirts even shorts come summer. look for quality leather and a sturdy sole, and you’ll have a pair of shoes that lasts for years. 

loafer here, here and here.

pointy-toed flat

if you want to add elegance to an outfit, pick a pointy-toed flat. the pointed toe visually elongates your leg. whenever you’re in doubt as to what shoe to wear a pointy-toe flat will work nine times out of ten. it’s a perennial favorite on my top 10 shoes for fall and winter.

pointy-toed flat here, here and here.

black pumps

if you only owned one pair of shoes, it would have to be black pumps. they go with everything. and are the perfect partner with suits or jeans. don’t forget there are a variety of heel heights to choose from. so pick a height that your tootsies will thank you for.

black pumps here, here and here.

nude pumps

just like their hard-working sister, the black pump, nude pumps go with everything. when in doubt on what shoe to wear i always reach for nude. dress them up for work or special occasion. nude pumps always make my top 10 shoes for fall and winter as they work hard for their money. they go with even the trickiest of color combinations.

nude pumps here, here and here.

leopard pumps

a pair of pumps will take you anywhere you want to go in style. and they look great with jeans as well as dresses. black and nude are the most versatile colors but don’t be afraid to add color!

leopard pumps here, here and here.

Chelsea boots

a cute ankle boot that soared to popularity during the swinging sixties is the Chelsea boot. who remembers the Beatles? as if we could ever forget the fab four. white boots are going strong this year. but black, brown or leopard are my top choices for Chelsea boots. elastic inserts on either side make it easy to slip into this boot. one reason it makes it onto my top 10 shoes for fall and winter.

Chelsea boots here, here, and here.

motorcycle boots

if you want a durable boot in the dead of winter to slosh through the slush, then consider the combat or motorcycle boot. this pair has been in my closet for several years. if i want to look stylish yet need a durable boot, this is the pair i reach for. it’s by a favorite brand of mine Frye based in Boston, Massachusettes. Frye has been making boots for over 100 years which is why i own several pairs. Frye boots are durable and stylish made from the best leather or suede. 

motorcycle boots here, here and here.

calf-high riding boots

i have to admit i have a soft spot for the timeless and classic riding boot. this boot has been in existence since the 10th century when riding boots were developed to make horseback riding more comfortable. several key design features were incorporated. the knee shaft protected the rider’s leg, a rigid toe was intended to protect their foot in case it was stepped on by a horse. and the sturdy heel helped keep the foot secure in the stirrup. this boot looks great with tights and a skirt. but a pair of skinny jeans and riding boots are a match made in heaven. that’s why a riding boot always makes it on my top 10 shoes for fall and winter.

riding boots here, here and here.

suede knee-high boots

suede is a more delicate fabric than leather so wear suede boots when the weather is mild. i picked up this pair from Vince Camuto at the Nordstrom Anniversary sale this year. i’ll be wearing these boots over jeans and under a skirt or dress all season long.

suede knee-high boots here, here and here.

there you have it, ladies. my top 10 shoes and boots for fall and winter.

About The Author

Beth Djalali

is the Founder and CEO of Style at a Certain Age. She writes Sundays-Fridays on all topics ranging from fashion, health, wellness, home design and more.

She’s 66, 5’8, and size 8.

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