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.

beth from Style at a Certain Age wears an Everlane grey cashmere crewneck, high rise black cigarette jean, Tory Burch black ballet flats and a double-breasted trench coat

ballet flats here, here, and here.

beth from Style at a Certain Age wears an Everlane grey cashmere crewneck, high rise black cigarette jean, Tory Burch black ballet flats and a double-breasted trench coat


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. 

beth from Style at a Certain Age wears a J.Crew cozy striped cardigan, Everlane cashmere crewneck, Talbots girlfriend jeans, J.Crew Ryan loafers

loafer here, here and here.

beth from Style at a Certain Age wears Ralph Lauren distressed jeans, Talbots cashmere turtleneck, J.Crew brown loafers, and Ralph Lauren glen plaid coat

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.

beth from Style at a Certain Age wears J.Crew polka dot chinos, Everlane cashmere waffle turtleneck, J.Crew Factory puffer vest, and Ann Taylor leopard flats

pointy-toed flat here, here and here.

beth from Style at a Certain Age wears a tartan plaid shirt, black cropped ankle pants, tartan plaid flats, military coat and quilted hobo handbag.

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.

beth from Style at a Certain Age wears a black cashmere Turtleneck dress, faux leather leggings and suede pumps.

black pumps here, here and here.

beth from Style at a Certain Age wears Anthropologie red pants, pink and red shirt, Everlane black raincoat, and black suede pumps

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.

2015 rewind

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!

beth from Style at a Certain Age wears an Everlane cashmere turtleneck, Italian weave ankle pants, leopard pumps, and Talbots green overcoat

leopard pumps here, here and here.

beth from Style at a Certain Age wears an Everlane cashmere turtleneck, Italian weave ankle pants, leopard pumps, and Talbots green overcoat

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.

grey zone

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. 

rainy days and tuesdays

motorcycle boots here, here and here.

ode to winter

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.

beth from Style at a Certain Age is wearing Ralph Lauren faux leather pants, chunky cashmere sweater, green utility jacket, Frye boots, and Frye hobo handbag

riding boots here, here and here.

talbots friends and family

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.

nordstrom anniversary sale goodies

suede knee-high boots here, here and here.

nordstrom anniversary sale goodies

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



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  1. carolyn wrote:

    Your article on shoes was just what I needed. Would you consider doing one
    on handbags also? Your handbags are always on point. I’d love some inspiration from you. Thank you.
    As always, you look wonderful!

    Posted 9.15.19
  2. Kathy wrote:

    I love your style! Maybe I’ve missed it, but it would be so helpful if you would also feature attractive shoes that are in the “comfort” category. Many of your mature fans would be most appreciative!!

    Posted 9.15.19
  3. Bonnie fraser wrote:

    Have you ever worn Ron White’s boots or shoes?
    Made in Italy but a Canadian designer. Apparently the Royals wear them also our Prime Minister’s wife. So comfortable & stylish.

    Posted 9.15.19
  4. Linda Lennon wrote:

    Hi Beth! Love all your choices! My Tory Burch ballet flats were sure worth every penny & have transitioned very well from NY to SoCal. How about a post on casual, slip on sneakers? I own a black Vionic pair, a navy Talbots and a neutral Skechers and seem to reach for those all winter long here. Since you shop so much better than I do, I would love to see what you find!

    Posted 9.15.19
  5. Janice wrote:

    Beautiful as always!

    Posted 9.15.19
  6. Julie Mycock wrote:

    Hi Beth, I think I’ve got most of the shoes/boots you’ve shown in your post. All are so versatile to wear with all outfits. A thumbs up xoxo

    Posted 9.15.19
  7. Cathy Cunningham wrote:

    Love every one of your top 10 choices. ❤️

    Posted 9.15.19
  8. Susan wrote:

    Beth the ootd with you in the lace dress
    printed wrap and nude pumps, takes my breath away! You look stunning!!!

    Finished my prep week Faster Way to Fat Loss, no gluten, no dairy and IF, not as difficult as I thought it would be. Thank you for posting, it was a push for me to join!

    Posted 9.15.19
  9. Carrie wrote:

    Beth, you are my inspiration! You look fabulous in these shoes and coordinated outfits. I have 5 of the shoes you have shown. Do I have permission to go and buy the rest?

    Posted 9.16.19
  10. Clara wrote:

    Great, I just order some loafers

    Posted 9.17.19
  11. Carolyn wrote:

    Thank you for all the time you put into writing this article.
    The lace dress with the orange floral wrap is one of my all time favorite looks of yours. Just lovely!

    Posted 10.4.20
    • that is one of my favorite photos and outfits. thanks so much for your sweet comment.
      take care!

      Posted 10.4.20
  12. Margarita wrote:

    Today’s blog is just perfect for those of us who are shoe lovers! 👠 ❤️ Thanks.

    Posted 10.4.20
  13. adrienne wrote:

    Gorgeous!! I want to look like you when I grow up😉. (I’m 54😂)

    Posted 10.4.20
    • awww, you just made my day!
      take care.

      Posted 10.4.20
  14. Susan Storrs wrote:

    I have noticed the return of the square toe and a movement away from the pointy toe shoe. Is that a trend?

    Posted 10.4.20
    • square toe shoes are indeed trending at the moment. but pointy-toed shoes are still in style.
      take care!

      Posted 10.4.20
  15. Pj wrote:

    Did you cut your hair? Although I wear a bob like the one you were wearing, I find the shorter look on you is amazing. We both have gray hair and I would love to go shorter, but with the shape of my face it just doesn’t work for me. Really just didn’t know if these where new or older pictures.
    Have a Blessed Day

    Posted 10.4.20
    • i cut my hair shorter over two months ago. but today’s post is from the archives so lot’s of photos from different time periods.
      take care!

      Posted 10.4.20
  16. Theresa Rollin wrote:

    Hi Beth,
    I love receiving your ‘ style at a certain age ‘ news every day. You are a glamorous small lady, always showing us mature gals clothes that would look nice on us. Unfortunately, some of us wear plus sizes Would it be possible to show us some clothes and boots, that are also available in plus sizes? I, and many ladies would appreciate that. I like the Talbot’s clothes and jewelry that you show. I tried ordering, but, they don’t ship to Canada.
    Take care and be safe.
    Theresa from Quebec, Canada

    Posted 10.4.20
  17. Kathleen McDermott wrote:

    Very helpful post, especially with the outfits featured. I have an appalling amount of footwear and am often overwhelmed when trying to pick the best shoe for an outfit. This will help me focus. I adore ballet flats, and would add oxfords as #11!

    Posted 10.4.20
  18. Paula wrote:

    Hi Beth; Love all your shoe/boot pics!! Wondering what your thoughts are on Dansko clogs?? I find they look great with preppy outfits!! Thanks!!

    Posted 10.4.20
  19. Tina wrote:

    My favorite pair was the motorcycle boots! I’m seeing a lot of combat boots in our stores. I think it’s fun to see an older woman in combat boots. It’s stylish and says I don’t really care what you think! Ha! I think I’m just too self conscience as I get older. I would love to see you style some. 🙂

    Posted 10.4.20
  20. Nelda M Pattillo wrote:

    Loved them all! I have had a love affair with shoes as long as I can remember! Any chance of a segment on purses? Also a favorite!!

    Posted 10.4.20
  21. Beverly Morris wrote:

    Beth… your style and tenacity….. I’m 68 yrs old, but I want to be like you when I grow up..😊

    Try as I might, I have not been able to find the VC suede knee high boots in this article. I’ve tried the Nordstrom site to no avail. I’m trying to lower my heels this year and those seem perfect.

    Pls help and thank you. Beverly/ATL

    Posted 10.4.20

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