The Business Casual Shoes I Can Actually Walk In (Yes, Even Over 50)
Every now and then, I get comments that ask for more “working gurl” outfits. I spend a lot of time working, but since I work from home, I don’t always think about typical office attire. When I think business casual, I want shoes that look polished enough for a business-casual outfit but don’t make me want to cry after an hour of wearing them.
Comfort and style can go hand-in-hand! These picks all have cushioned insoles, good structure, and a little personality. Perfect for a day at the office, running errands, or dinner out without needing a shoe change in your car (we’ve all been there). If you’ve ever struggled to find work shoes for women over 50 that feel as good as they look, I’ve rounded up a few favorites I can actually walk in, no break-in required.
Comfortable Business Casual Shoes That Actually Feel Good
Quince Pointed Toe Ballet Flats
You can never go wrong with a timeless leather ballet flat. Think soft, buttery leather in neutral shades like beige, blush, or camel. These are perfect for work, casual outfits, or even travel days when you need a comfortable yet polished shoe.
- Classic style
- Neutral color that goes with everything
- Versatile enough to pair with dresses, jeans, or shorts
Eileen Fisher Leather Sandals
These Khaki Leather Sandals are comfortable right out of the box with a cushioned footbed that makes long days on your feet a breeze. The khaki shade is a neutral classic that pairs easily with any outfit. I have become a HUGE fan of Eileen Fisher shoes! I’ll admit, I was surprised that their shoes are so comfortable.
- Cushioned sole provides all-day comfort for sensitive feet.
- Neutral color elongates the look of your legs.
- Adjustable straps ensure a secure fit.
Classic Flats and Sandals for All-Day Comfort
Talbots Vera Patent Mary Jane Ballet Flats
These sweet Mary Jane Ballet Flats are a classic, but with a nice two-strap detail. I love the color and the patent crinkle finish. And of course, a cushioned insole so they’re comfy.
- Crinkle patent finish adds subtle texture
- Cushioned insoles for comfort
- Strap detail keeps them secure without being fussy
Sam Edelman Alie Ballet Flat
This little Ballet Flat comes in the prettiest colors for fall. There are a lot of options, including a fun blue version for a pop of color. I’m partial to this shade of brown this year, and my closet is already bursting with chocolate/cafe. These are lightweight and flexible; they are perfect when you want something simple but elevated.
- Soft leather upper
- Cushioned insoles for comfort
- Stylish color that freshens up neutrals
Sam Edelman Kasey Square Toe Ballet Flat
I love a square toe for something modern. These toffee suede Ballet Flat add a little bit of edge while staying elegant. They’re comfy and easy to dress up with trousers or down with jeans.
- Square-toe shape looks sleek
- Soft suede upper
- Flexible sole for easy walking
Loafers That Are Both Stylish and Supportive
Loafers are such a staple this time of year, and these business casual loafers for women offer everything from flexible soles to polished finishes. You can wear them with ankle pants, denim, or even a midi skirt and still feel pulled together.
Talbots Audrey Nappa Loafers
How luxe do these Nappa Loafers look! Made from nappa leather, they are made to mold to your feet. Wear them with slacks, ankle pants, or even jeans for a classic vibe. They’re called the Audrey. Do you think these are Audrey Hepburn inspired, maybe?
- Timeless, structured loafer design
- Padded footbed for all-day wear
- Great with both tailored and casual outfits
Sam Edelman Elaina T-Strap Buckle Loafer
I love that these are a bit rugged. Business casual doesn’t mean boring! These T-Strap Loafers are chic, unexpected, and comfy with their cushioned insoles. They would look fabulous with cropped pants or a great pair of dark denim jeans.
- Unique T-strap detail for extra style
- Suede finish adds texture
- Cushioned insole for all-day support
Old Navy Faux-Leather Pointy-Toe Loafer
Budget-friendly and super versatile, these Pointy-Toe Loafers look way more expensive than they are. They slip on easily, have a bit of structure, and the sleek shape works with slim pants or wide legs.
- Affordable and stylish
- Lightweight with a comfortable fit
- Easy slip-on design
Old Navy Faux-Leather Loafers
The chunky sole and heel keep these Loafers from being boring. Plus, they’re another very affordable option! Reviews are good with people saying they are comfortable and fit true to size.
- Simple design for casual outfits
- Comfortable to slip into for quick trips
- Great with cropped trousers or jeans
Affordable Work Shoes That Don’t Skimp on Comfort
If you’re looking for affordable work shoes that don’t sacrifice comfort, Old Navy has some surprisingly stylish picks. These are great for anyone building a business casual wardrobe on a budget.
Quince Leather Pointy Penny Loafer
You know that Quince is my fave! These loafers from Quince have that classic penny loafer style with a modern, sleek pointy toe. They’re made from quality leather, and the fit is tailored but flexible. I already own this Soft Leather Loafer that I wore all summer, so I think I need this pair for fall.
- High-quality leather upper
- Classic style with a modern silhouette
- Comfortable for all-day wear
Quince Leather Lug Sole Loafer
If you need a little more grip and edge, these Leather Lug Sole Loafers are perfect. They’re a little more expensive than the Old Navy version, but hey, they’re Italian leather! The bone color is fresh for fall and works with just about everything in your closet.
- Lug sole adds traction and trendiness
- Soft leather for a polished look
- Great paired with wide-leg trousers or slim jeans
These supportive shoes for office wear give you the best of both worlds: comfort and confidence. Whether you’re at your desk or dashing to an appointment, you don’t have to choose between style and stability.
👟 Guess the Shoe!
Guess the 5-letter shoe word. You have 6 tries!
How it works: After each guess, the box colors will tell you how close you are:
Green = correct letter in the correct spot,
Yellow = letter is in the word but in the wrong spot,
Gray = letter is not in the word.
FAQs About Comfortable Work Shoes
Q: What makes a shoe “business casual”?
Business casual shoes are polished but not overly formal. Think ballet flats, loafers, or low-heeled sandals that pair well with trousers or dresses.
Q: Are flats or loafers better for all-day wear?
It depends on your feet! Flats are lighter and more flexible, while loafers usually offer more support. If you walk a lot, loafers with a cushioned footbed are usually best.
Q: Can women over 50 wear trendy shoes?
Absolutely! Comfort doesn't mean boring. Many of these picks have modern shapes, colors, or details that keep your style current without sacrificing your feet.
Comfortable Work Shoes for Women Over 50: Final Thoughts
Finding the perfect pair of business casual shoes can be tricky, but these give you a solid mix of comfort, style, and versatility. I love that these stylish, comfortable flats don’t just look good, they actually feel good too. That’s something I never take for granted anymore! Whether you’re a loafers-all-day kind of gal, love a pretty flat, or need something easy to slip on, these shoes can handle your workday and still look good when you head out for dinner after.
Which ones are calling your name? Are you Team Loafers, Team Flats, or Team Both?
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😀. Love my loafers!
Comfort is key. Thanks for the suggestions. 😊
2nd guess
😊 Fun game; I love Wordle. My favorites are the Quince ballet and the lug sole!
😀got it the first try! Maybe because I have been looking a pair of that kind of shoe for transition weather & had it on my mind! Lol
Again, I can’t find the smiley, but I got the word game on the second try. I play that one daily on Words with Friends with no categories. Love it!
Am I not understanding the game? I typed in a 5 letter shoe word and it was put at the top all in green, but then I couldn’t type any more words in. Aren’t we supposed to fill in all the boxes with shoe words? Am I missing something? (LOL probably)
All green means you guessed the correct word. You could play the game again since it would load a different word if you want.
🙂 I love Quince and their products. I would look into these ballet flats!
😀 I got this one on the third try. But I like the match game best.
I like the Match game best!
Whew!! Got it on the 4th try. I like the different choices of flats that still look nice for work.
Liked both games, however the “wordle” type game, I couldn’t get it to “work” properly.
Thank you for introducing me to the Quince ballet flats a few months back. They are so pretty, comfy, and classy. I also recommend Birdies and Rothys. Lots of options!
Loved the word game. It was not as easy as I thought it would be.
🙂 I have gotten rid of all the shoes in my closet that were not comfortable. If I couldn’t wear it all day, it’s gone. The majority of shoes that I own are Vionics.
😊 SHOES!!! When in doubt- shoes. Lol
🙂 Like this game too.
🙂 I liked both games, I play wordle every day, got it in 3.
🙂 I’ve always loved a good penny loafer. Thank you for such a variety of options as well! This game was more of a challange for sure.
Some very cute choices!
Fun game! Two tries! Great selection of flats!
the pointed toe loafers look cute. like all of the games so far. I love games!
Love the square toe Sam Edelman ballet flats. And so does my bunion. lol
Got it in two tries. Fun game .
Thank you for your creativity.
I guess I’m not so good at Wordle any more. 🙁 I like the chunkier loafter types. I don’t dress up much any more. I usually wear my sketcher sneakers or sketcher sandals. I do like wearing boots in the fall and winter.
😊I like them all!
I also could not get the game to work. It would not let me type in a letter.
Loved the game. Got in 2 tries.
☺️Loved the shoes. This game was my favorite!
🥰I like a wordle game. I play several every day. I’m leaning towards the ballet flats because they feel more feminine.
Comfort is a must.
Got it in 3. Fun game.
😊 I like Talbots ballet flat. The word game didn’t work for me. I’ll keep trying!
🙂 could not get the word game to work. I liked the Quince loafer.
🙂 Finally got it! Harder than you think!
I need a shoe with a wide toe box. The Sam Edelmen T-strap shoes look like they they would be good for me – the strap looks like it could be adjusted.
🙂
I really like the earrings that you are wearing in the first photo. Could you remind me where they are from?
Completed the word game on my 2nd guess!!
Here is the link to the earrings: https://amzlink.to/az0LifdKcV12C
Ilove that Quince is selling shoes now. Game was fun
🙂 I could not get the word game to work!
I’m sorry it didn’t work for you.
Type your guess into the Enter your guess line. It took me several attempts to figure out how to play. Hopefully you can get it to work!!
😊 I like this game too. I love the Khaki Leather Sandals and Quince Penny Loafer.
🙂cute shoes. I liked the quince.
A
Wordle-style version for fashion! 3 tries
🙂 I really like the Khaki Demo Leather Sandal the best. Got it on the second try. I didn’t think I would like this game, but I do now.
I’m so glad you liked it!
I like the Vera Ballet Flats. All of the shoes are nice but the Vera are my favorite.
Loved both games!
And the shoes.
I’m terrible at wordle-style games!
I usually start with a word like aisle so that I can get a lot of vowels. That make it easier to figure out the word.
Very cute shoes! Yay….got it,….play Wordle every day!
I’m glad you liked the Wordle-Style game based on shoes
🙂 This penny loafer would look great with just about anything!
love it!
very fun!! games are good at brain! Thank you 😊
🙂My favorite is the Elaina t strap
Yay I got it! Another wordle-style game for the day! 😀
Found it 🙂 The shoes are cute.
🙂
Couldn’t get this game to work on my iPad.
Love all the loafer styles.
Hmmm, I know it works on desktops, laptops, and phones.
🙂 Love the Quince loafers!
😊Love the Quince pointed toe loafer and the Sam Edelman t-strap loafer!
Oh my, the game was hard but I solved it, after 2 tries LOL.
The word will change, so you can try several times.
Love the song
The Sam Edelman T strap loafers are my favorite. Unfortunately sold out in my size in the toffee suede. The game was fun!
Love all the loafers & the game
😊I love loafers and boots! Bring on fall!
The games are fun.
Thank you
love the penny loafers, they look so comfortable. I love the Joe stories 😍.
😀would love to try some shoes from Quince – they look so nice!
Enjoyed the “Wordle-Style” game 😊
Thanks! My mom loves games like this.
😀team flats
🙂 Great shoes! I really like comfort and flats alot of the time. TY!
☺️ love a comfy pair of loafers.
😀 very nice and professional
🙂 I like all of these shoes.