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5 Essential Fall Shoes Every Woman Should Own

Happy Thursday, ladies!  The past few weeks I’ve shared 5 fall essentials and 5 more fall essentials that every woman should have in their closet.  Today, I’m drilling down into one of my favorite topics:  shoes.  I’ve got 5 essential fall shoes.  Today, we’re talking:

  • pumps;
  • Chelsea boots;
  • loafers;
  • pointy-toe flats; and
  • motorcycle boots.

Just like with my other essentials, these are all classic shoes that will stand the test of time—worthy investment pieces, particularly the boots.

For each shoe.  I’ve pulled together two inspirational outfits that show you how to style them.  And just like a few weeks ago, for each item type, I pulled in 4 of my favorites from my favorite retailers.

The Summary

  Today I’m focusing on 5 essential fall shoes every woman should own

 The outfits I’m sharing are old, but I’ve built similar boards for them

 For each essential, I pulled together 4 of my favorite picks from my favorite outfitters

5 Essential Fall Shoes Every Woman Should Own

1. 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

Similar outfit

Screen Shot 2022-09-22 at 12.37.12 PM

Board:  Daphne Topcoat (J.Crew) | The High Wool Ankle Pant (Ann Taylor) | Cable Knit Turtleneck | Calf Hair Pointed Toe Pump (Nine West) | Marilyn Round Sunglasses (Talbots) | Xena Suede Clutch (J.McLaughlin)

Shop the Board

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

Shop Pumps

2. 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.  Black and brown are my top choices for Chelsea boots. Elastic inserts on either side make it easy to slip into this boot.

grey zone

Similar Outfit

Screen Shot 2022-09-22 at 12.57.50 PM

Board: Mid Rise Ankle Skinny Jeans (Wit & Wisdom) | Cashmere Classic-Fit Crewneck Sweater (J.Crew) | Rivoli Corduroy Blazer (Banana Republic) | The Citywalk Lug Sole Chelsea Boot (Madewell)

Shop the board

10 wardrobe essentials

Shop chelsea boots

3. Loafers

What can I say about the mighty loafer except it goes with so many outfits? Straight-leg jeans, skinny jeans, skirts—they all work perfectly. 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 Ralph Lauren distressed jeans, Talbots cashmere turtleneck, J.Crew brown loafers, and Ralph Lauren glen plaid coat

Similar Outfit

Screen Shot 2022-09-22 at 1.38.04 PM

Board:  Logo Timeless Trench Coat (Banana Republic) | Cable Knit Turtleneck Sweater (Talbots) | The Corinne Lug Sole Loafer (Madewell) | The Slouchy Boyjean (Madewell)

Shop the board

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

Shop the outfit

4. 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 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

Similar Outfit

Screen Shot 2022-09-22 at 2.08.11 PM

Board:  Quilted Barn Jacket (Talbots) | High-rise Slim Demi-boot Pant (J.Crew) | Turtleneck Tunic Sweater (Ann Taylor) | Wanda Pointed Toe Flat (Sam Edelman)

Shop the board

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Shop pointy-toe flats

5. Motorcycle Boots

If you want a durable boot to slosh through fall rain or winter 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.

rainy days and tuesdays Screen Shot 2022-09-22 at 2.34.21 PM

Board: Slim Ankle Jeans (Talbots) | Puff-Sleeve Crewneck Sweater (J.Crew) | Checked Scarf (Ann Taylor) | Veronica Short Slouchy Boot (Frye) | Checked Scarf (Ann Taylor)

Shop the board

ode to winter

Shop motorcycle boots

In Case You Missed It

This morning, Kelly shared some of her favorite skirts to transition into fall. Click the title or image below to read the article.

Kelly’s Fall Skirt Picks

About The Author

  1. Cyndi Anderson

    Question Beth, are the J Crew School Boy Blazers in style and the original Bass Penny loafers?
    Love the daily fashion tips. I have been following you for years. We are the same age and born in the same wonderful month of August.

    1. Carolina Girl

      I have the same question as Cyndi: Are original Bass Penny loafers in style? Thanks, Beth.

      1. In my humble opinion, Penny loafers are a timeless classic that never goes out of style. I wear simple loafers like Bass non-stop throughout the fall.

        1. Carolina Girl

          Thank you, Beth! Answers my question.

    2. Hi Cyndi,
      In 2022, blazers are more oversized than schoolboy blazers and loafers have lug soles. That said, I still wear my schoolboy blazers from J.Crew and Penny loafers are a timeless classic.
      Hope this helps.

  2. Diane

    I’m 65 and have been following SAACA.
    Today, I put to use ALL of the great advice you offer. While in TN, I visited Tanger Outlet, and went to the stores you shop at recommend.
    Today’s purchases:
    Black Knit Blazer, Crop Boyfriend Jeans Loft Outlet
    I also found a few great items at Talbots, and Chicos.
    Thank you for opening up my eyes to SAACA.

    1. Hi Diane!
      I am so pleased to hear your shopping expedition was a success!
      Thanks so much for being here; we so appreciate you.

    2. Janeen Casella

      Hi Beth!
      I love the spiky gold necklace you wore with the tan corduroy blazer and Chelsea boots. Would you share where you found it? Thanks, Janeen C

      1. Hi Janeen,
        That necklace is years old from Bauble Bar.
        Hope this helps!

  3. Marcia B

    Hi Beth, Iโ€™ve noticed you wearing eyeglasses more often. Could you do a tutorial on how to pick glasses that compliment your face?

Navy Coat winter outfit

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for women

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