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!

Similar outfit

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

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.

Similar Outfit

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

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.

Similar Outfit

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

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.

Similar Outfit

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

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.


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

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

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.
I have the same question as Cyndi: Are original Bass Penny loafers in style? Thanks, Beth.
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.
Thank you, Beth! Answers my question.
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.
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.
Hi Diane!
I am so pleased to hear your shopping expedition was a success!
Thanks so much for being here; we so appreciate you.
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
Hi Janeen,
That necklace is years old from Bauble Bar.
Hope this helps!
Hi Beth, I’ve noticed you wearing eyeglasses more often. Could you do a tutorial on how to pick glasses that compliment your face?