Hi, Deborah and JoJami,
I would love your advice on how not to look frumpy when I have to wear clunker shoes because of foot problems. Because of an old skiing injury, I have been unable to wear heels since I was in my 20’s, which makes it hard to look and feel sexy, or even professional, when I want to dress up. I’m limited to certain brands of shoes recommended by my foot doctor and orthopedic surgeon so it’s not just a matter of being able to wear flats.
For example, I’d love to wear leggings this Fall as shown in the photo on your website, but I can’t wear heels.
I’d appreciate any advice you can give me. Many thanks!
- Nancy
Dear Nancy,
We sure wish we could wave a magic wand with your problem, but it is not that simple. However, your problem is one that many women face. We get letters all the time from women that can not wear heels.
That being said, you can still look fabulous but just have to try styles that might not be the latest trends.
The good news for you is that with styles changing so often, almost anything goes when it comes to pant styles.
When you are stuck having to wear clunky shoes, there are several things to make sure you do not do. First off, is leggings will be out of the question for you. Since the style is really a “pencil” shape, no matter what you do, legging will just not look good with a clunky shoe. Instead, you will need to opt for any pant that has a wide leg and (or) has some flair at the bottom.
This will still be stylish, and you can wear almost any shoe. Also, there are some great brands of shoes out there that do sell some comfortable shoes that don’t look orthopedic.
Here are some styles from Zappos.com that we suggest:
 These Taryn Rose flats are comfy and stylish |
Actually if you can wear this type of flat shoe you could still wear it with a skinny jean and look great! |
 This is good with pants only! |
Once you have to start wearing more orthopedic looking shoes like these, you can easily see that style starts going out the window. |
 Another simple but elegant choice |
However once again, if you wear these with the right style of well-fitted pants, you will still look great! |

fashion vending machine for ballet flats
Leave it to my (JoJami’s) niece Abigail to share with me the latest in fashion vending machines!
Have you ever been out late at night in your heels and just find that final walk back to the car can be a real pain!
Here is a vending machine that doles out little ballet flats you can slip on when needed!
Just thought it was amusing and actually really enjoyed the rest of the site too.
It is called The Frisky.com...and I must admit, I think we can all use a little more “frisky” in our life!!!
Wondering how to dress after 40 to look sexy and hip, but still age appropriate? Buy yourself a pair of tall boots! Be they high heeled or flat, boots that cover your calves and sit just below the knee are alluring, chic, and ageless.
Here are 9 Top Tips for How to Wear Tall Boots:
1. When wearing pants tucked into flat boots make sure the boot is tight enough around the calf, so there’s no gap. Any gaping will make your legs look twice as bulky.

2. Boots are most flattering to the leg when they go all the way up to the knee like these chic Croc boots. Be picky, don’t buy a boot that is 2/3 length, unless you will be only wearing them under pants.

3. A suede boot will always be the best choice for comfort.

4. If you have large calves, choose a pair of these Viva Spiga rouge boots with hidden elastic goring that adds stretch at the 15 inch circumference collar.

5. Avoid boots with too many straps or too much bling on them. A simple classic boot looks more elegant and age appropriate and won’t date as fast.

6. For comfort, a wedge heeled boot is a great option. You’ll be able to walk for miles in comfort and still look tall!

7. The newest style of boot has an asymetrical cuff at the top of the boot. It’s a very youthful look and is meant to be worn with a more casual outfit. If you want to give it a try, wear your flat cuffed boots with jeans. Don’t spend too much on these boots as they are super trendy and might not be the “in look” next year.

8. Don’t forget to pair your boots with tights for a modern look. Nylons are too lightweight and will make you look dated. Black tights (or leggings) would be great these gorgeous black suede boots. Your tights should match the color of your boots in order to elongate your legs and make them look lean and sexy!

9. The slimmer the outfit the slimmer, the finer the boot. For example, a slim skirt and chunky, heavy boot like these DON’T mix. Best to save these for pants.
