What Not To Wear

Don’t you just hate those proclamations? I do. What not to wear was a very popular television show about 15 years ago which I could not watch. The premise was that a style “felon”, who was nominated by family and friends, would agree to throw out their current wardrobe and be given $5,000 to go shopping for a new one.

Stacy London, Clinton Kelly, and the viewing audience would watch this “felon” (not my word) shop while the two hosts critiqued what they chose. I couldn’t watch it without my stomach-turning. Seeing a woman ridiculed for her shopping choices may have made for interesting television but I felt they were needlessly demeaning her.

Whew…OK, I got that off my chest. Now let’s talk about what not to wear. The things we choose to not wear for no other reason than the limitations we put on ourselves.

Doesn’t it always seem easier to narrow down the styles and fashion you would absolutely never wear? The ones that feel too old for you.

For me, there are several things starting with orthopedic shoes because although my feet would feel wonderful in them, they make me feel ancient. That means I’m always on the hunt for comfy shoes with a modicum of style. You’ll also never see me wearing elastic waistbands, that show. I love the easy comfort of pants and skirts elastic waistbands but I never let them show.

How about the fashions you’d never wear now because they seem too young for you? The ones you’d feel silly wearing lest someone thinks you look like “mutton dressed as lamb”.

What about fashions we won’t wear because of our aging bodies? Sleeveless comes to mind as does short items where our knees and elbows are on display. Why are we limiting ourselves at a time when time itself seems so much more precious?

There is a style that never seems to look too old or too young. It’s classic style. A pair of chinos with a button-down doesn’t look appreciably different on a 15-year-old or an 80-year-old. What is different is how you style it and the accessories you add. That makes classic garments ideal for investment dressing so you can buy fewer items of better quality.

And so right about now, I’m reconsidering trends. I know they help to keep us looking current, but at what cost?

I would love to know, is there a style you avoid like the plague because of your own prejudices?

Be well and remember to wear what makes you feel confident.




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  1. Joan
    May 27, 2020 / 1:40 pm

    First, I found your assessment of What Not to Wear interesting. I used to watch that show all the time and loved it. But I would have preferred to watch a “regular” person getting makeover/updates. Some of the people they chose were pretty outrageous in their style choices beforehand. And those episodes when the person was very emotional and spilling their guts on camera were a bit “over the top” for me.

    As for my personal style choices, many things are dictated by my current body. For instance, while I might consider wearing sleeveless, I can’t because I need to buy a size large enough to cover my hips but then it gaps at the armholes giving a clear picture of bra, etc. Like you and others, fashionable heels are a thing of the past. I can’t even wear a small wedge because I tend to twist my ankle and fall. I have never liked the preppy look for me. I like colors and patterns but don’t buy based on trend or style. I buy because I like the outfit and it looks good on me. There are many shapes and sizes that no longer work on my sadly overweight body. I constantly struggle to lose weight but without success. So in the meantime, I dress for the body that I currently have and hold onto all those wonderful outfits in my closet (many still with tags) that I hope one day to fit back into.

  2. Anon
    May 27, 2020 / 1:14 pm

    That show was really about people who were living in the past. The lesson is that we all do, to varying degrees. So I’ve got some clothing to donate now.

  3. Pat
    May 27, 2020 / 12:59 pm

    With my 60th birthday approaching, there are somethings I won’t wear anymore. Two years ago, I had to accept that high heels would need to go. I threw away those that were worn out, gave some away to a niece, and sold others. I have been purchasing stylish flats – boots, loafers, mules, sandals, slides, sneakers and lower block heels or wedges. My back thanks me daily….;-) In terms of clothing, I try to look at trends critically and assess why I am drawn to the trend, then I figure out if it can be adapted to my lifestyle and age and my look. Lots of times, I have an item in my closet that can be adapted to look on trend and current. I rarely “invest” in trendy items, but I may be willing to purchase an inexpensive item that is on trend because I know I will use it for the next year or so and will get my money’s worth. I do invest in high quality core and basic items that I know I will wear for years to come, and I am willing to pay a bit more for higher quality craftsmanship, great fit, and natural fabrics. I don’t want to be uncomfortable nor do I want to look younger. I want to look stylish, chic, and confident at my age – and comfortable in my own skin. I avoid clothing that is too tight or too revealing. My style is mostly classic, but I adapt some trends that appeal to me with out going overboard. I wear some skirts and lots of trousers or slacks (for work) and straight-leg or skinny jeans (for casual) – I pair these with tanks, tees, turtlenecks sweaters, shirts, and silk blouses mostly in solid colors. I have some tanks, shirts, and blouses in classic prints (animal, polka dots, plaids, etc.) to mix it up a bit. I have lots of blazers and cardigans that I use as the third completer piece. I have both work and casual dresses as I find them easy – one and done. These days, I review my closet regularly and donate or sell items that don’t flatter or get little wear. I am pretty happy with my wardrobe and can shop my closet to create a look. I am now investing more in accessories – silk scarves, belts, French Kande jewelry (purchased my first piece based on your recommendation, Jennifer), and higher-end luxury handbags and shoes.

    I loved What Not to Wear and Stacy and Clinton. I did not think they were mean; it seemed that they were presenting the woman with an approach that would make her look better and feel more confident in her clothes. In many cases, the women had never learned to shop properly. That is me. My mom taught me to look for good value and how to tell if a garment was well made, but not much about what fit and flattered. She is a good dresser, but I do not think she tried many trends. She has a style and a look and a uniform that has been the same for all my life. I did learn to care about my appearance from her. I learned what I did not know from reading fashion magazines and trying things on. I felt like Stacy and Clinton were personal stylists. I loved both their books, and now have a collection of style books that inspire me regularly. It was always an interesting process to watch in each episode. Many of the women featured embraced the opportunity to learn how to flatter their body shape and it was inspiring to see them feel better about themselves. Some were less open to the process, and those were painful to watch in some cases. I actually learned a lot about how to select items that flatter my body. What was more interesting to me was that I learned to “trust the process” in all aspects of my life. I feel that I am more open and flexible as a result, and not just in terms of my wardrobe choices. I remember someone once telling me that an outfit I was wearing was a What Not to Wear outfit and looked fabulous on me. I still remember that outfit as it was one of my favorites and I wore it till the top and pants nearly fell apart and I had to throw them away. I still have a version of that outfit in my closet!

    Thank you for creating space for this great community to share our thoughts. Be safe!

  4. Kay
    May 27, 2020 / 12:07 pm

    For some people, physical handicaps make the fashion decisions for them. I imagine my shoe styles would not appeal to the able-bodied.
    I have physical issues that make heels impossible for me, as well as buttons and zippers on pants. Fortunately, my arms are still good and I wear sleeveless all the time. My boho-esque style works for me. What would I absolutely never wear? Spandex.

  5. Karen
    May 27, 2020 / 11:50 am

    I never go sleeveless in public, partly from avoiding sunburn and partly because I’d be cold.
    I love bright tank tops with a cotton shirt (often a man’s white shirt) open over it in the summer. At 62, I love wearing bright colours and patterns that make me smile and often include a cotton scarf in my look.
    I haven’t ever found a pair of regular capris that fit me right, but I love capri and bicycle-shorts length leggings with a longish tank or peasant blouse.
    My work in the community allows me to dress casually but not sloppy or low-cut.
    Living on the West Coast my winter style is slim jeans, flannel shirts, fleece hoody vests and classic + ethnic wool sweaters with my Blundstones.
    Great reading all the comments.

  6. Eve
    May 27, 2020 / 11:44 am

    I gave up wearing peasant blouses in the summer because I thought I was too old to wear them. Thank God, I decided this year to give them another try. I am having so much fun getting dressed now. It’s gets hot here and these are perfect.
    My comfort level is somewhere around straight leg, hi rise jeans, shirts, v neck soft blouses and loafers, tennis shoes, sandals with little to no heel. Loose soft, unstructured jackets in winter and boot, boots, boots. Bomber jacket, denim Jacket. Don’t follow fads or most trends.

  7. Janet
    May 27, 2020 / 11:11 am

    I also remember the teasing if pants were too short so I have never worn cropped or capris. Also white socks were considered tacky when I was young and I still can’t wear them. So strange how these childhood impressions stick.
    I have never liked animal prints or large florals, also nothing lowcut in front or back. I only wear athletic gear when exercising. Athletic shoes and all boots have always been too hot for me. I’m fortunate not to have any foot problems and go barefoot at home but I’ve never been able to walk in heels. I never wear shorts in public but would definitely wear a shortish skirt.
    Thanks for letting us express ourselves!

  8. Pam Curtis
    May 27, 2020 / 10:36 am

    I wore distressed jeans and oversize flannel shirts as a broke art student and again as a broke young mother. I am not interested in revisiting that look (although I like a distressed hem on a jean). Cold shoulder tops look cheesy to me – not a fan. I do like the look of a modest off the shoulder top. I would love to be wearing dresses, especially in the summer but they no longer suit my 70-year-old pear to apple figure. A bad knee means its flats for me but I have found cute and comfortable options in Vionics and Taryn Rose for my retail job.

  9. Susan B
    May 27, 2020 / 10:15 am

    I enjoyed WNTW. I think they really cut back on demeaning people in the later episodes. I generally found their advise quite helpful. Sometimes when an outfit doesn’t quite feel right, I think of Stacey’s advice mantra, color, pattern, texture, shine, and can usually think of something to add that just hits the right note.

    I like a basic classic look, but with a spark to keep it modern and interesting. I know several women who wear mostly classic, but end up looking dowdy and a wee bit like the Queen Mum. I want so badly to add a scarf, layered necklaces or fun earrings. But of course, they are entitled to dress as they please and I would never say anything unless asked, which occasionally, I am.

    I love the look of a crisp white button down shirt. I buy them occasionally, but they never seem comfortable. It seems like I’m fighting with them the whole time. I either have gaps or the shirt is so big to fit my girls, that it feels like a tent or a lab coat. I’ve tried taking in the sides or putting in darts, but usually end up wearing them as a topper and eventually giving them away. I just need to settle with the fact that this style is not for me.

  10. beth byrd
    May 27, 2020 / 10:09 am

    This was such a great post, Jennifer. I’ve enjoyed reading all the responses and can relate to so many of them. Similar to several others I will be 62 this summer.

    I’m still working in an office (albeit office casual) so my work clothes are bit less casual than when I am at home. However, I will not wear bare legs with a dress/ (unless it’s a maxi), won’t wear cropped pants (ankle length yes), no cold shoulders and no distressed jeans.

    My feet are extra wide, but I refuse to wear shoes that have that orthopedic look. I’ve had much success with Cobb Hill, Aravon and Clarks.

  11. Nancy Walden
    May 27, 2020 / 10:00 am

    Your body definitely changes as you age. My waist has thickened so I no longer tuck in my tops. No mini-skirts for me! I like my skirts at mid-knee or at the bottom of my knee. I always wear tunics with my leggings. I love classic pieces however I’ve never liked chinos and button-downs. It’s just not a look I’ve ever liked on me, even when I was younger. I have a lot of sleeveless tops and, even though my arms are beginning to look older, I am not ready to give them up. I like comfortable shoes and won’t buy one that isn’t. When it’s cooler, I wear a lot of flats. I can’t tell you how many sandals I own! They’re my go-to most of the year. I bought new heeled sandals for my granddaughter’s wedding My dress is a classic sheath with an attached sheer “cape” that camoflauges my problem areas.

  12. Elaine @ Following Augustine
    May 27, 2020 / 9:46 am

    I clearly remember the day when I stood in the girls changing room after gym class and watched some of my classmates struggling back into their girdles. Never will I ever wear something like that, I vowed, and I never have! On the other hand, there was a time when I swore I’d never wear an underwire bra and I’ve been wearing them for years! I’ve learned never say never where fashion is concerned (except maybe to girdles!) When I was younger, I refused to go sleeveless because my arms were so skinny, but now, as a 67 year old who regularly bench presses 100 pounds I love wearing sleeveless tops and dresses in the summer.

  13. Cathy
    May 27, 2020 / 9:43 am

    sometimes shorts and sleeve less have to work during warm weather and outdoor exercise – but I also have not found any store or brand that would offer what I would like – exercise or running shorts in the same light fabric that barely cover knees – also yes these are much more flattering that crops . Even Chico’s and I kill don’t have light loose
    Shorts to cover knees. Will keep looking!

    • Linnie S Z
      May 29, 2020 / 8:01 am

      That is what I am searching for as well! Jennifer, any suggestions?

      • kate
        May 29, 2020 / 8:18 pm

        Cathy, they are expensive, but the Lululemon Align 10″ short is of this wonderful lighter weight material. For an exercise short they are great. I also wear mine with a tunic for during the day.

  14. Marian
    May 27, 2020 / 9:43 am

    Such a great discussion!

    I don’t wear brown or beige because my mother thought they went so well with my eyes, that I wore them too much until my twenties, when a friend once asked me why my I was afraid of adding color to my wardrobe. Ouch! But she was right! My whole closet was really drab.

    I learned a lot from WNTW. But the British version (came first) was better! The 2 female hosts made some awful comments but they also had shows where we saw them – they themselves chose badly and improved. You can see them on YouTube.

  15. Catherine
    May 27, 2020 / 9:43 am

    sometimes shorts and sleeve less have to work during warm weather and outdoor exercise – but I also have not found any store or brand that would offer what I would like – exercise or running shorts in the same light fabric that barely cover knees – also yes these are much more flattering that crops . Even Chico’s and I kill don’t have light loose
    Shorts to cover knees. Will keep looking!

  16. Catherine
    May 27, 2020 / 9:42 am

    I am a bit
    With one earlier reaDer – sometimes shorts and sleeve less have to work during warm weather and outdoor exercise – but I also have not found any store or brand that would offer what I would like – exercise or running shorts in the same light fabric that barely cover knees – also yes these are much more flattering that crops . Even Chico’s and I kill don’t have light loose
    Shorts to cover knees. Will keep looking!

  17. Holly
    May 27, 2020 / 9:02 am

    I will not go out of the house in shorts or sleeveless tops anymore. I cannot wear button down shirts because if they fit across the chest then the shoulders are huge & they always seem to gap, so I prefer pullover tees & sweaters. I do not like cropped or Capri pants, so stick with full length pants. I did watch WNTW
    With my friend & we always found it entertaining & informative. I confess when we were out in public, we would people watch & occasionally spot someone & then look at each other & say: What not to wear!
    Enjoy reading everyone’s comments

  18. Linda GR
    May 27, 2020 / 8:37 am

    I have decided to leave cropped pants and leggings in the past. I used to buy them because that was the fashion, but I am bring true to myself from now on. I prefer ankle pants in natural fibers, and boot cut Jean’s in all colors. I’ve gone back to button shirts tucked in, and the well made, good quality knit pullover. I’ve started to replace items in my closet and I am much happier.

  19. Jo
    May 27, 2020 / 8:34 am

    Apparently everyone loved this post. Reading the responses was as much fun as reading the original. So great to have a “conversation” during these isolated times. Thanks, Jennifer!

  20. Cynthia
    May 27, 2020 / 8:28 am

    I am about to turn 70. I have tried to wear a classic button-down with a pair of chinos and absolutely hated it. Never me, never going to be me. I love boho, lace, kimonos, embellished jackets, and jewel tones. I avoid ruffles and anything tight or revealing. My favorite look is a long top over leggings or slim pants (leather in winter) and ankle boots. In the summer I wear breathable cropped pants or capris under a lightweight boho top (bright colors, breathable fabrics, embellished with embroidery or other pretty trim). I wear comfortable supportive sandals or Skechers.

  21. Sheila in Garden City SC
    May 27, 2020 / 8:21 am

    I must go for the classic look always, khaki and denim are timeless. Retirement has given me a more casual lifestyle but I’ll wear pearls any day of the week. I owned an orthopedic shoe store many years ago, prefer to say comfort shoes though. The Comfortable Shoe, loved my little shop! Slimsation is a great brand to consider for your pull on pants, capris, or shorts.

  22. candice clement
    May 27, 2020 / 8:18 am

    My only complaint about other women is when women who should know better show ugly knees. I truly believe there is a time when knees should no longer be shown, especially when they look like a double chin. I have seen this on the most slender of women, it is not a good look. WNTW did teach me why I need a V or scoop neck and they were right. I already knew about the bra.

  23. Ann
    May 27, 2020 / 8:16 am

    Count me in with the Vionic fans! They saved my feet. I refuse to wear cropped pants; I have some bad mental images of them as “old” (especially on me) – but I don’t mind lightweight pants that are above ankle for summer. I’m giving a second thought to my love for a flowy boho look since so many here say no to that, hmmm…is that a bad thing? I do wear leggings but not as often as I used to, and only with a decent-length top – no way does a shorter top/too-tight leggings look good on anybody who’s not in the gym. I love fun dresses in summer instead of shorts. Not too-young-fun, LOL, but a nice knit t-dress that’s not too tight, etc. I’m also with the crowd here who say no to sleeveless, ugh, BUT…if it’s really hot, it’s silly not to. I think the thing that I wonder most about these days is that, on my formerly slender-ish self, in mid-60s I’m getting thicker around the middle. I don’t like tops that are too tight, but when I default to my usual bigger tunic tops, etc., sometimes they look like I’m hiding more “huge” than is really there. I want to find a happy medium.

    I’ve just recently found your blog and I’m so glad I did!

  24. Sandy
    May 27, 2020 / 8:11 am

    Ok, I am 68, I no longer have my girlish figure, I love leggings, crops, and Bermuda shorts. I thought I was too old for the deconstructed jeans but my mother who is 85 wears them and cold shoulder tops and looks amazing in them, so I feel they are ok if you like them. I have never been a girly girl so I don’t care fore ruffles, butterfly sleeves, lace, crochet etc but I do like pattern rod. Paisley. I used to avoid reds, pinks, corals, because I had a ruddy complexion but now I can wear any color except yellow. Because of a serious ankle/leg fracture, I can no longer wear heels or any sandals that fit around my ankle.

  25. Diane
    May 27, 2020 / 8:10 am

    At 72, I wear pretty much what I want. I have my own style that is fairly conservative. I don’t like cold shoulder, ruffles, capri pants, short skirts, most florals and sleeveless tops. If I wear anything sleeveless, I make sure I can wear a lightweight jacket or sweater. I do not wear platform shoes but do wear pumps with kitten heels. I wear Jamaica or Bermuda shorts, but always use self tanning lotion when I do. I like flowy maxis and midis, and almost any type of pants, (wide straight or skinny leg.) I don’t wear leggings very often, but when I do, it is almost always with boots and a long tunic top. You must cover the bum! ( This is mostly in the winter.)

  26. Linda
    May 27, 2020 / 8:08 am

    I dress in clothing that makes me feel comfortable, That includes my shoes. Due to Rheumatoid Arthritis, my left foot can’t wear “normal” pretty shoes. I am in the orthopedic shoes , which throws off my dress. So for now, I just dress in what is comfortable to me. It doesn’t always look good to the outside world and I am sorry about that but comfort means more to me than others acceptance of what I must wear at this point in time. I plan to get my foot fixed and that will open a lot if now closed avenues for me.

  27. Kate
    May 27, 2020 / 7:53 am

    I have many things I won’t wear! Sleeveless/short sleeved tops, unless I have a third layer. Anything that shows my heavy legs—shorts, skirts, leggings, jeggings, skinnies, ripped jeans, capris, ankle or cropped pants (I need a 34” inseam, so these remind me of the days when I couldn’t find pants long enough—they were derisively called “floods”). I don’t wear white pants—reminiscent of my old nursing uniforms, and they don’t flatter my pear shaped figure. Uncomfortable shoes, heels, or that are too wide for my 11 AAA shoe size.

  28. Phyllis Hughes
    May 27, 2020 / 7:44 am

    Vionics, Naots, and Clarks are wonderful for people with bad feet. I won’t wear ripped jeans, cold shoulder styles, or the half tuck. Oh, and unhemmed anything. I seldom wear shorts because my knees get cold and too many visible veins on my legs. I do like leggings because with a tunic length top they are modest, but make my legs look good. I seldom wear dresses, but keep saying I am going to get back into wearing them; at least maxi length dresses. I feel like pantyhose are a necessity for shorter dresses.

  29. Susan
    May 27, 2020 / 7:29 am

    What Not To Wear For Me- at 63 years of age, 5’2” and curvy- ripped, frayed jeans- too trendy and not elegant, cropped anything-unflattering proportions and too revealing, cold shoulder tops- dated and impractical, neon colours-unflattering, camo, animal, large floral or abstract prints- ugly to my eye, low necklines- not for daytime wear, high heels- unfortunately uncomfortable, plastic jewelry- can do better, hair ornaments- too juvenile, shorts- find skirts more flattering, baggy or tight tops- can do better….

  30. Gloria
    May 27, 2020 / 7:23 am

    I am 62 and was and still try to be fashionable. I love sleeveless and shortsleeve in summer with long flowy skirts, capris and a lot of cute tops!! I still have a decent figure so I feel fortunate I can pull off some slightly form fitted clothes.
    HOWEVER, two years ago I had to forgo any type of fashionable shoes for my part time retail job and any type of on my feet activity. My extremely flat feet totally gave out and I wear heavy duty orthotics in my shoes. It was and still a very life changing moment and my moments of feeling totally put together are gone. It took a lot of soul searching to realize I just want to be healthy and pain free and this is the price I have to pay if I want to be ambulatory at the finish line. I have tried all types of shoes, but my feet are so bad there is no choice. Age and life changes things, but we adjust. But hey I look great and fashionable from the knees up!

    • Cindy
      May 27, 2020 / 7:36 am

      I feel exactly as you do ( and I will be 62 this summer). I’ve been searching for cute, supportive shoes for a few years now. Can you share what you’ve found? I live in Berkenstocks and Vionics in the summer.

    • Nancy
      May 27, 2020 / 7:47 am

      I am 67, have very flat feet and feel your pain!! I have ortho inserts and my podiatrist told me never to wear shoes without them. However, I spent 6 weeks in Japan two years ago and not wanting to go against customs, I began to go barefoot in the home I was staying. I felt that I could always put them back on if needed. Surprisingly, by the time I got home, my feet were less painful and I continue to go barefoot when I can. My feet are still flat and standing long periods is painful. I wear Rockports and a British brand Hotter, but I believe my feet are stronger and more a agile with yoga stretches and going barefoot at home.

      • Debbie Bell
        May 27, 2020 / 8:11 am

        I had a highly recommended Oysio Therapist tell me that orthodics are Best ysed temporarily in favour of giving your feet the chance ro repair themselves and having better posture than we sometimes do when wearing extreme ones.
        I find inserting my orthodics in boots or shoes with little support, such as ballet slip ons is enough time spent with them.
        Of course, in ten years, everything may change ….grrr!

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