7 Fashion Mistakes I Avoid Over 50

Today, I'm going to share with you 8 things that women over 50 never wear. If you’re interested in fashion over 50, follow along to avoid a few common fashion mistakes.

Please feel free to cherry pick these tips! Take what you find helpful and leave what you don't.

1. No short and tight dresses

The first items I’ve retired from my wardrobe as a woman over 50 are short and tight dresses with nothing else. 

If I’m planning to wear a short and tight dress, I’m going to make sure that I pair it with a third layer, perhaps knee high boots or panty hose. 

More often than not though, I tend to skip this trend all together for an outfit that I feel comfortable and confident in.

Instead of a short and tight dress, I love a midi dress for my fashion over 50 ladies. 

This denim piece looks like a skirt and top but it’s actually a dress. It looks flattering plus it feels comfortable and chic. 

Pair it with faux fur and heels or go for a more casual vibe with your go-to sneakers.

2. No tight dresses and skirts without hose

I also avoid tight, short dresses and skirts without hose or opaque tights.

By the time you reach your mid-50s, your skin may appear crepey. For me, I don’t feel my most attractive with that much skin showing. 

Instead, I’d wear a dress like this cute houndstooth piece. It’s a one-and-done, easy-peasy dress which I paired with opaque tights, slingback mules and a Gucci coat.

3. No crop tops

The next fashion rule I follow as a woman over 50 is no crop tops! If I’m going to wear a crop top, it will be with high-waisted denim, but honestly, I haven’t really been wearing crop tops at all.

Instead, I like to sport cropped jackets with high-waisted denim in 2024. They’re incredibly chic and are trending really hard right now. They look amazing with the wide-leg denim trend. 

Another great thing about this cropped denim jacket is that it will transition well into spring because of the lighter color combination. 

I’ve paired the jacket with these super flattering, wide-leg, high waisted jeans that are so good that both Kathy and I own them!

I’m 5’4 so I’m wearing them with gold platforms which give me a few inches, making me look taller. 

4. Off-the-shoulder tops or cut-outs

My next fashion no-no is off-the-shoulder tops or cut-outs.

These can look nice on some people but for me, when I move around or just sit down, they become unaligned, some skin might hang out and this doesn’t feel flattering to me. 

What I do love is a striped shirt and a bomber jacket! I love the sherpa fabric paired with faux leather. 

I’m also wearing black denim and boots to complete this look. 

5. No sky high stilettos 

Simply put, sky high stilettos are uncomfortable and when I wear them, I can’t walk! Considering fashion over 50, my maximum heel height these days is about 4 inches. 

I’d reserve these beautiful, suede, 4 inch pumps for a date night since that’s not an all-day event. 

A black, suede pump is a timeless shoe that will polish off so many outfits. 

 Cuffed denim is trending really hard this year. My top is a gray bodysuit and my outer layer is a chocolate brown bomber jacket. 

7. No overly ripped denim

I avoid overly ripped denim, but I would still wear a pair of jeans that are more subtly ripped, like these:

Most of the time though, I will opt for jeans that aren’t ripped at all. I’ve paired these jeans with this perfect, camel colored cashmere sweater and a black, long sleeve, sweetheart neck sweater. 

While I might wear minimally distressed jeans, Kathy, on the other hand, will not wear ripped denim at all. She finds that the skin looks unflattering when it is pushed through the ripped sections. 

An alternative look that Kathy loves is pairing denim (no rips) with a tucked, cashmere sweater, a faux fur jacket and boots. 

Fashion mistakes to avoid over 50

No matter your age, let us know in the comments which fashion mistake you’ll be avoiding this year and onward!

Next, learn 10 chic ways to style fall’s hottest fashion trend: fashion over 40.