You are currently viewing 87 Fashion Mistakes that Make You Look Old
Coach bag, Max Mara boots, Statement belt, and self-sewn shirt dress

A listicale of the most common fashion mistakes that make you look old, but that you can easily avoid. Tips are given as well.

  1. Don’t Dress Yourself Old
  2. Watch Out for these Fashion Mistakes to Not Look Old
  3. Top of the World Style linkup No. 257

Disclosure: There are affiliate links in this post.

Don’t dress yourself old

Remember back in high school when we were fresh(wo)men and tried to look older than we were? Remember when we dressed in power pants suits, pearl necklaces to come across more experienced when we graduated from college, when we dressed for a job interview and when we were on our first job?

In the retrospective, it makes us smile. Today, we try everything to look the best ever in midlife, turn fashion into style, not age pre-mature, fight these under-eye dark circles even when it is hopeless because they are not a discoloration, but an inherited “hole.” You can’t fill it, and hide it. Depending on the light it just shows, no matter how great your concealer or makeup is.

Oh, if we had known back than how bad the sexy tan would be for our skin! We are the last generation of women who laid in the pool on a floating silver mattress. We used the reflection of the water to enhance the UV radiation to get an even darker tan. Some of us even lay down between mirrors or had a subscription to the It tanning studio in town. If only!

Well, of course there are anti-aging creams out there and they are pretty good. I tried several of them. When you missed them check Zenmed anti-aging cream review, or the Snowberry serum review at the links.

However, it’s not only our body that can make us look old. Styling mistakes can do that too. The good news is that we are in control of our dressing and can avoid the mistakes that make us look Old Lady.

Watch out for these fashion mistakes to not look old

However, we shouldn’t overlook that there are so many things we can avoid that make us look old. And, yeah, of course, just keeping attention to these 85 most common mistakes can go a long way.

  1. Mom jeans.
  2. Elastic waistbands.
  3. Cardigans on plus size women.
  4. A cropped jacket with low-rise jeans.
  5. Shawls or capes instead of a coat.
  6. Mommy robes.
  7. Muumuus.
  8. Baggy cargo pants.
  9. Three piece suits – read skirt, blazer plus vest, or pants, blazer plus vest.
  10. Rompers.
  11. Overalls and jumpsuits.
  12. Wearing holiday sweaters.
  13. Flannel shirts.
  14. Crochet sweater, vest or jackets in Woodstock 70s style.
  15. Crochet bikinis.
  16. Short, tight and clingy knits.
  17. Fair Isle crew-neck or sweater vests.
  18. Boxy shapes or baggy shapeless clothes to hide love-handles, a tummy, saggy arms, etc.
  19. Tweed skirt suits, tweed anything that is styled conservative, i.e. matronly. See this post how to wear tweed right over 40.
  20. Tan pantyhose.
  21. Body conscious or tight clothes in metallic. See this post for how to wear metallic right over 40.
  22. Wearing more than one brocade item in an outfit.
  23. Metallic tops with leggings and stiletto heels.
  24. Washed out or acid wash jeans. Remember, we were teenagers or kids when we sat in the bath tube with our jeans on and brushed the thighs so they jeans looked “washed?” We were just a bit older when we used bleach to distress them.
  25. Jeans or jackets with an ethnic print. If you love them wear learn how to look ageless in ethnic prints right over 50.
  26. Tie-dyed anything.
  27. Big shoulder pads.
  28. Over-embellished anything.
  29. Fussy details like little gold or flower-like buttons
  30. Knit sweaters with pom-poms and/or fringe all over the place.
  31. Laura Ashley like garden prints, prairie prints and other sweet prints that would look cute on a kiddo.
  32. Palm Beach floral prints outside of a vacation resort.
  33. Any animal prints in tight, body conscious, shiny or short clothes.
  34. Mixing different animal prints in one outfit when it is not a trend. You are not the advertising board for the zoo. See the link for how to look sophisticated in animal print.
  35. Souvenir or college Tees when you are not working at a university/college. It is how long ago that you graduated?
  36. Meant-to be funny Tees like “The bags under my eyes are … (add you favorite bag brand here)”, or “My face is up there.” It’s not funny, it is tasteless, and no taste is for sure opposite to personal style.
  37. Retro-style short cardigans with embroidery, beading and/or sequins unless your personal style is Romantic. However, the older you get the harder this personal style is to pull off.

Don’t know what your primary style is? Take this free style analysis quiz.

mature fashion blogger in floral boots and DIY corduroy dress
Max Mara floral print boots, self-made corduroy shirt dress, Hermes collier de chien bangle, and statement belt (all own)
  1. Ruffles, embroidery, sequins and beading all in one outfit.
  2. Items with quarter size or larger sequins. Any sequins larger than a pinky nail look just plain cheap. Period.
  3. All expensive designer clothes in one outfit. Recall money doesn’t equal style.
  4. Whimsical tiny necklaces.
  5. Necklaces and/or rings that tell how many kids/grand kids you have. For many men it lowers your market value.
  6. Your kids’ or grand kids’ photos as background or screen saver on your cell phone. Go for your pet, something hobby-related or a hot sport car instead.
  7. Über-bling, i.e. jewelry in  all possible places including the toes. You are still too young for this style. Only Iris Apfel can rock this look.
  8. Wearing over-sized earrings or loops that are the size of your bangles.
  9. Cheap (fake) pearls and chains look just plain cheap on us over 40, while they look great on Millennials.
  10. Accessories from just one designer in one outfit. It looks immature and non-confident. A designer doesn’t mean style, they design fashion. Style is picking and choosing what works for you to turn fashion into personal style. Read why buying only designer clothes fails to make you look effortlessly stylish.
  11. Wearing the wrong bra so you get a uni-boob or quadruple boobs,  saggy boobs or to high boobs.
  12. Not wearing the right shape-wear or no shape-wear at all.
  13. Wearing a corset or bra visible under a pants suit.
  14. Granny undies. Yes, there are underwear issues.
  15. Reinforced toe stockings or pantyhose.
  16. Comfort or orthopedic shoes that look like what they are. There exist stylish orthotics.
  17. Chunky 2.5 inch (5 cm) or lower heels with formal or semi-formal attire. So Old Lady!
  18. Shock absorbing white sneakers with jeans. So 70s senior high and high school students.
  19. Sneakers with socks outside the gym.
  20. Penny loafers.
  21. Wearing these Mary Janes or slider type plastic shoes with round wholes and foot-bed no matter how funny the print or how cool the color is anywhere else than in the yard for gardening. Doing so conveys the message “I gave up on me.”
  22. Flip flops anywhere else, but at the beach, no matter how embellished or expensive they are or what designer designed them.
  23. Wearing these faux shearling hideous shapeless boots, which look like a foot brace. you know these boots that every teenager is wearing. And no, it doesn’t make them look more stylish when they are covered with silver sequins. Sorry Heidi Klum, it probably wasn’t your idea.
  24. Wearing sky-high heels you can’t walk in. Exercise walking in your heels before you go with them in public (e.g. wedding, opera, date night, girls’ night out).
midlife style blogger looking posh chic in a 40s retro corduroy dress
Retro style self-made corduroy shirt dress with leather buttons, Hermes collier de chien bangle, purple statement belt for a pop of color, Coach lavender bag, and Max Mara floral boots (all own)
    1. Wearing the wrong shoes with respect to your pants’/jeans’ leg width or the length of your skirt/dress.
    2. Outdated accessories including shoes unless your personal style is eclectic style.
    3. Matching shoes and bag. So 1960s and 1970s. What did you do in the 1980s, when Patricia Gucci mixed it all up in the name of Gucci?
    4. Wearing an old-fashioned or distressed bag.
    5. Reading glasses hanging on a necklace around your neck. You convey the message that you would loose them otherwise.
    6. Bifocal glasses with demarcation line. Yuck!
    7. Fit-overs instead of prescription sunglasses or instead of contact lenses plus great modern sunglasses.
    8. Dated or boring frames, especially, round comic type granny frames.
    9. Coke bottle lenses.
    10. Half glasses.
    11. Skin on all burners, read short skirt length, large front and back cleavage, bare shoulders and arms all in one outfit.
    12. Butt cleavages, exposing the Y of your thong, belly button or your love handles.
    13. Too much skin. Go for sexy colors and fabrics instead. Show skin strategically. Less is so much more sexy. #midlifestyle Click To Tweet
    14. Too long or too short skirts or dresses.
    15. Cut-offs and short-shorts. Just wear shorts in an ageless style way.
    16. Wearing any color that washes you out just because it is the color of the year. Who cares about the It color anyway? You can fake the look of Pantone colors with look-alikes.
    17. Any color close to your face that enhances your wrinkles, e.g. black.
    18. An unnatural look, i.e. pieces with weird or odd proportions.
    19. An outfit all in matching girly pastels or sludge brown.
    20. Wearing too many trends or no trends at all in one outfit.
    21. Wearing your daughter’s (or grand-daughter’s) clothes.
    22. Looking like you tried too hard.
    23. Looking like you didn’t try at all.
    24. Dark eye circles.
    25. Little Laura Ashley like prints.
    26. Menswear from head-to-toe. See the post at the link to get it right.


I am sure there are many other points that make us midlife women look “old” at least in the eyes of the young like typing text messages with our index finger. What do you think is the thing that makes a person look old? What do you think is the biggest fashion mistake that makes a midlife woman look Old Lady? I would love to hear from you.

When you are interested in getting it right in any dressing situation, you may be interested in my style recipe book How to Dress for Success in MidlifeBuy it now.

midlife fashion book is available on amazon

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Top of the World Style linkup No. 257

Top of the World Style linkup party every week on Thursday

Welcome to the 257th Top of the World Style linkup party.

lipsticks in various pinks
Mimi’s post at In My Primetime became the Top of the World OOTD Readers’ Fav. Photo from her post.


Christine of Bon Chic Style in hat and blush skirt suit with shirt, belt and pumps french style outfit
Christine of Bon Chic Style became Top of the World OOtD My Fav. Photo from her post.


Top of the World Style Winner Penny Kocher in olive jumpsuit, sneakers, denim jacket, head scarf and scarf mask
Penny Kocher of Frugal Fashion Shopper became Top of the World Style Winner. Photo from her post.


Congrats Ladies! Grab your award buttons.


Gateway to the party


See these awesome looks at the Top of the World Style #linkup party. #timelessstyle Click To Tweet

Photos of me: G. Kramm

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