I’m still trying to figure out what an older person is supposed to wear

By Caitlin Kelly

It’s got to be tough to maintain standards if you were once the fashion director for both Vogue and Harper’s Bazaar, as was Paul Cavaco, a New York City fixture in the stylish world.

Harper's Bazaar
Harper’s Bazaar (Photo credit: Wikipedia)

But I was struck by his comment, the headline to this post, as it resonates for many women I know, mostly those of us north of 40.  Good to know it’s a challenge for some men as well.

Bits of you head south. Bits of you are little less appealing, (upper arms, upper thighs), than they once might have been. The late Norah Ephron wrote a whole book, published in 2008, called I Feel Bad About My Neck.

Choices that are cute or fun in your 20s and 30s suddenly start to look cheap, tacky and weird in later decades. Grooming — hair, nails, pedicures and (yes, please!) trimming men’s nose and ear hair — becomes even more essential. Careless starts to look disheveled.

For years, I’ve loved watching the TLC television show What Not To Wear, and have learned a lot. But it’s ending next month. Noooooooooo!

So…what to wear?

Do you know about this terrific blog — Advanced Style? Ari Seth Cohen focuses his lens only on older New Yorkers with panache.

Have you heard of Iris Apfel? Now 91, the self-described “geriatric starlet” gave an interview to Harper’s Bazaar in April, 2013. I liked this:

If your hair is done properly and you have on good shoes, you can get away with anything. That and having a good attitude — try to keep yourself on an even keel. All the plastic surgery in the world isn’t going to help if you are unhappy.

My father just turned 84 and, when he dresses up, still sets a very high bar for elegance — navy blazer, polished loafers, a silk pocket square. My husband, in his 50s, is known around his Manhattan office for a splendid array of socks and ties. I bought him a great pair of fawn suede Lacoste sneakers as my wedding gift.

I see far too many women in their 50s and beyond who look like hell, as though they have simply folded the tent of style, (if they had one in the first place) and jumped the express train to schlumphood. No, I say!

I’m not arguing for the size-2-ropy-arms drama very prevalent in the wealthier precincts of America, as much a uniform as a diktat. But surely we have better options than crappy haircuts and dumpy clothes?

Russian VOGUE magazine - April 2011
Russian VOGUE magazine – April 2011 (Photo credit: jaimelondonboy)

Then what? Shop where?

For me, it’s a varied mixture of vintage, J. Crew, an H & M shift, a bit of designer, some classics: an Hermes silk carre or a pair of Ferragamo suede loafers or an Edwardian necklace.

Then something unexpected to shake the whole mess up. This week I did something utterly out of character, emboldened by a surprise check, and bought a big, blingy watch. I wear it loose, like a bracelet. It’s a hoot and I love it.

The worst sin we make as we age is to give up, to stay stuck in a style rut, to assume that color and wit and fun is something only enjoyed by the young ‘uns. There are several women on my apartment floor who are north of 80 and look great — sparkling eyes, make-up, coiffed hair, fab outifts. Bless them for being a role model.

And so I still read Vogue and Bazaar and Elle and Marie-Claire. I buy very little of what they suggest — both the sizing and prices shoving much of it beyond my reach — but I have fun keeping up, knowing what the cool kids are wearing, and sometimes snagging an H & M copy for $30 or $50 instead.

I’m more willing to invest real cash on great shoes, accessories and jewelry.

Ladies and gentlemen, how has your look changed as you’ve aged?

Any fab shopping tips/sites to share?

37 thoughts on “I’m still trying to figure out what an older person is supposed to wear

  1. Fit. Always important, imo it’s more important as you age. A well fitted outfit can make the least expensive dress look fabulous, and a poor fit most expensive look like trash. And a good bra can make a world of difference.

  2. Well said! The difference between a well-fitted bra and poorly-fitted one is quite amazing. Thanks for the reminder! 🙂

    Too few people remember that many items can be tailored, as well. It seems to be a lost/forgotten art.

  3. I don’t have anything in terms of tips, really, except look how you want to look and keep up the proper hygiene. Then again, I’m not sure what you’re talking about when you say older people looking like schlumps. A lot of the adults I know look very well dressed and aren’t slobs at all. If anything, the only appearance issues they may have are weight-related.

    1. You may be in a specific sub-set…I live in a building with many older people, all of whom have sufficient incomes to keep things going. Women tend to disappear from public view/notice as they age and some just give up and don’t care. I think it’s sad. Vanity is silly, but self-care is healthy.

      1. Indeed. And I think I do live in a different sub-set: Midwestern people, some of whom are Jewish and regularly attend synagogue and many of whom have professional jobs. It makes sense for them to keep up appearances.

      2. Exactly.

        When I go into NYC I can always tell who the foreign tourists are (clothes, shoes, accessories, hair color) and who is NOT from NY but from…somewhere else: pastels, fanny packs, horrible haircuts (sorry, but true) and color, tank tops and super tight/short shorts in midtown, the most conservative part of the city.

        I was very struck when I moved here from Montreal (which is one seriously stylish city), how few NYers have much style, either…many just dress super-conservatively or expensively (i.e. to impress and minimize business/social risk). Zzzzzzzz.

  4. For a long time I mocked the fashionable and looked at them only as people who were materialistic snobs who valued only Things. As a result, I refused to wear a suit and even did the bare minimum that the Army would accept when it came to my appearance. I simply didn’t want to be the materialistic, shallow and judgmental person I (often incorrectly) perceived.

    Then, I was hired by my current director. He required that I wear a suit and tie to work. Grudgingly, I went to The Men’s Warehouse and a few other stores to pick up what I needed for work. I probably would have done the bare minimum yet again, in protest, were it not for the earth-tone green tailored suit that I picked up. I put it on – and felt like I was Brad Pitt, only cooler. I realized that wearing the clothes meant that I could feel a little better about myself. It’s helped me develop a healthier self image, advance my career, and ensured that I was respected in situations when I was otherwise less-than-optimally prepared. I’ve gone from a guy who generally thought he was ugly to realizing I’m at least average and in the right outfit I’m a sexy beast. Clothes can’t grant confidence, I don’t think, but they can bolster it significantly. I think a lot of people just get busy and forget that, or like me, they maybe never learn it until they’re forced into the lesson.

    I’d still rather be wearing my Ren-faire costumes though. 🙂

    1. Thanks for weighing in with such a great story….that’s pretty much my point.

      I work alone at home about 90% of the time and, I admit, it’s easy to schlub around my small town when all I’m doing, alone, is running boring errands. But in any professional situation — I had two Manhattan meetings this week with new-to-me people — I absolutely want to up my game. It’s challenging for me to figure out what to wear, though, as journalism is an odd blend of corporate and creative. I don’t have to wear anything as formal as a suit, but I have to be careful not to get too boho. I also work with many people 20 to 30 years younger, so looking stuffy and prim is not a good option, either.

      No matter how much we may whine about it, we all form instant, snap — often permanent — impressions of people and much of it is based on dress, grooming and confidence. I want mine to be positive and hope they are!

      Suits, when well-chosen, well-fitted/accessorized and well-worn, can be very sexy indeed! 🙂

  5. Camping for more than a week without access to even a blow dryer has a way of making you reevaluate your look. Even though we had showers and loos available, there was not a lot that could be done to look presentable when reduced to wearing clothing that had been rolled up in a bag. I put a little make-up on to make myself feel a bit more presentable … not enough for anyone to notice really, but I felt better and I couldn’t help hearing your voice when I was standing at the mirror as I imagined you saying ” Makeup? You’re camping! ”

    Which leads me back to your post on style and wardrobe. I was okay when I wore suits and was a size 6, but now I live in tiny village in England where it tends to be chilly and grey and my waistline is becoming harder to locate. Since my old body appears to have decamped permanently, I am going to have to have a makeover fairly soon that doesn’t involve a charity shop or the Salvation Army sale racks.

    * Sigh *

    1. Oh dear…transAtlantic nagging?! 🙂

      I hear you. It’s much tougher at our age. I find *some* dresses both forgiving and flattering and you can accessorize the hell out of them. I have a few that I can layer a sweater over in the fall/winter and toss on opaque tights and boots. Maybe when I get there (spring 2014 is my goal) we can go shopping!

      Sounds like a shopping trip to a larger city is in order…? Might be worth checking out some great online stores as well…ASOS has a lot of too-young stuff, but some is cool and very affordable. I also love Plumo, based in the UK. Not cheap, but really interesting grownup stuff.


      This dress is on-sale and perfect! A scarf, some cool, low boots…rock it!

      1. It is perfect! That look is great for my short-waisted self. Cool low boots … I may need to consult with you on those when I find some. Thanks for your help. 🙂 I feel like I have a place to begin. (Spring of 2014 sounds great)

      2. You are not going to believe how much money I spent clothing shopping online last night (until 3:00 AM) after your blog post and our fashion ‘chat.’ The darling dress you suggested was not available in my size, but I found a few, (notice I said a few) at Land’s End and Macy’s that were. A wool winter coat (less than 1/2 price) and several swimsuits found their way into my online cart as well and did I mention tops? Yep, there are a few of those winging their way to my step-mom’s house in Marietta too. Fortunately both stores have easy return policies and I didn’t have to pay for shipping. Last thing, it was all on sale which is good because I’m going to need some new shoes now.

  6. This is all so interesting, Caitlin. Even going to the grocery store I put on something decent and certainly a little makeup and earrings. But decent here may mean denim capris and a nice top. The west is very casual but when I go out to plays and concerts I try to look spiffy. I do shop at consignment stores but mainly for jewelry – Mexican silver – as I have a bit of a thing about wearing previously worn clothes. Canada was very stylish so when I moved to New England; I looked totally out of place – talk about frumpy! When I moved west, New England frumpiness had to go but I still refuse to buy into the fringed jacket/cowboy hat set. I recently bought a lovely grey tunic dress with an interesting hem – with a nice scarf, jewelry and black tights it will look great this winter. I love scarves and scoop up the best I can find. I think your personality and body type have to figure into your style – I would look ridiculous in anything flouncy, tailored looks best on me.

    1. I love consignment shops — I drive 20 minutes west to Greenwich, CT and score triple-ply Neiman Marcus cashmere cardigans for $100 (usually $600+ new) and wear them for years; rich ladies wear their clothes for 15 minutes!

      New England almost killed me. I couldn’t bear all that Puritan, no makeup, no bright colors, ugh! That was also pre-Internet and I was broke and a 2 hr drive each way from Boston so it was impossible to find anything I liked. I was very glad to flee.

      Sounds like we have similar taste. I like simple lines and solid colors and then have lots of great scarves in linen, silk, cotton and jewelry and shoes/boots. I’d rather shop for those (and can get some great stuff used as well) than for clothing. I always score great things when I got back to Toronto and Montreal (more European choices there than here) and also when I travel. I got great stuff in Tucson and last fall in Decatur, Georgia when I spoke at the literary festival.

  7. Wow, do I ever resonate with this. I have a select few boutiques I visit and I haunt the LL Bean catalogue. Shopping in department stores upsets my stomach. I’m inspired by Gloria Pritchett in “Modern Family” but have no idea where to buy styles that will flatter my hourglass figure. Why are so many women’s clothes designed to fit boyish physiques? Since I go to the barn every day I wear mostly jeans or breeches and a shirt of some description. I love cowboy boots and an upscale country look. My taste runs to the classic, and whatever I select from the rack is invariably the most expensive. I like a decent sale but won’t shop one just for the sake of it. You won’t catch me crossing the border to get a deal. I shop when the spirit moves and that is usually when I’m most successful. Still, when my ship comes in I plan to hire the services of a fashion stylist and figure out how to dress this body with which I’ve been blessed once and for all. … Great topic!

    1. I was really lucky — in spring 2011, and started doing a lot of public speaking and TV to publicize my book, I blew some very serious coin at Neiman-Marcus and came out with an entire wardrobe — after the dept. manager took me in hand and brought every single piece to the dressing room for me. I loved it all, (and I loathe shopping, am short-waisted and curvy) and that was an eye-opener. A very good stylist will be very helpful indeed.

      One of my tricks is to buy a dress or skirt with some stretch in it, (not slutty, short, shiny or see-through, of course) and throw a great cardi over it. I got a fantastic cherry red cotton sheath at H & M for $50 or so and wore it to give a speech. The accessories (and Spanx!) up the game.

      One of my favorite websites — a 40s retro look but really pretty, often made in silk — is Trashy Diva, in New Orleans. I bought one of their dresses on a visit there and got compliments every single time I wore it.

      I love this dress…

  8. Pingback: Broadside Prompt – What’s in YOUR Closet? | themodernidiot

  9. I love following fashion as an artform. Though I may disagree or shake my head at some of the material or compositions used in some collections, I love looking at the vision and seeing the body celebrated as such. And some of these visions and collections are innovative and truly spark inspiration, which is what any artist hopes to do with their work. So, yes, “What to wear” is a big question indeed, but with a very simple answer:

    “Whatever the f*** you want.”

    Seriously. That’s no cop out-wimp answer. That’s a BIG answer! That’s “I defy what I’m dictated!” “I defy what is expected of me and live my truth!” “I am my own art, I speak my own voice!”

    Regardless of your body type or age, when you feel magnificent, you are. It’s really that simple! And in my heart, I believe that’s what the whispers behind the shouting in fashion are really trying to say: You are a work of art. You are your own canvas, your own song, so compose the notes yourself and dance to that tune to your grave. In the meantime, live your truth.

  10. I’ve probably regressed with age. From smart in my early teens to hippy by my late teens heading eventually for casual jeans in my thirties. From the forties onwards it’s been mainly smart slacks/chinos, shirt and waistcoat ( vest). My greatest pleasure in my late fifties and now in my sixties is to wear a frock coat when I go out somewhere nice. The natural elegance of the Edwardian era has great appeal and I’m hoping to be a trendsetter if it ever comes round with kids again.
    xxx Hugs xxx

  11. Mary Portas, would be the ultimate woman to design and dress women of age and distinction! She had a television show that gave viewers and inside view to her collection, and the process to providing the public (a demographic of older women who were not being marketed toward) with stylish, modern, sexy clothes.

    I fucking love her. Look her up…watch the show too, she’s brilliant.


  12. I believe that fit is most important and something that is difficult to achieve when buying bargain clothes. If I feel good wearing something I feel more confident. More often than not I regard the people who are slaves to fashion as appearing ridiculous because they don’t choose items that are right for their bodies. You need to be aware of what works for you.

    1. I agree.

      But it’s not easy…too many people larger than a 10 or 12 just fall into baggy, no-shape clothing because they are so frustrated trying to find flattering clothes. Too many manufacturers save $$$ with cheap fabric or unflattering cuts — like a sleeve that is short/tiny — when something with even two or three more inches in length would work better for an older woman. I have little patience to spend my days looking for stuff and it can be very time-consuming.

      1. I do exactly what they say not to do on What Not to Wear… If I find something that I like and is flattering I buy it in every color. I really dislike shopping now that I’m older and I wonder if it is because nothing is really designed for my age group.

      2. That show has been hugely helpful for me! I’m really going to miss it. Stacy has a new book out, though, which is worth reading.


        I agree, very few clothes are designed for women older than 40. The assumption is that we’re all (hah) still skinny and toned enough (if we ever were) to wear things that are short, tight and poorly cut — or sheathe ourselves in muumuus. I will buy anything anywhere I think is going to work…opaque tights, great shoes and accessories and top-notch grooming help a lot.

        I had to do a formal event a few years ago and did a Carolina Herrera copy — got a gorgeous taffeta skirt for $80 and threw on a white LL Bean cotton shirt. I added a flea market deep green silk sash, black high-heeled boots…very YSL circa 1972. Looked great, felt great. It takes imagination!

        The worst look is mutton-as-lamb. I see a lot of that here.

  13. I like fabrics with some structure/stiffness to them, which are forgiving of any bumps because they don’t cling. Classic is good. Simple is good. I also find that design styles from the 40s and 50s were very flattering to women’s bodies, and I always get compliments when I wear modern versions of those styles — think about June Cleaver’s clothes with different shoes and hair –they still look great on a woman, even now! Classic styles are classic because they stand the test of time. The important thing to remember is that good clothing can be just as *comfortable* as bad clothing, if it is well made, with a good fabric and fits you properly.

    1. All true. Part of it, for me, is expense. I am loath to spend a lot of money when I’m trying to drop two dress sizes…at least one. But I have three structured cotton sheath dresses and they’re great.

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