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Style · 23 picks

23 Things Women Over 60 Wish They'd Worn Sooner

The red coat didn't need a special occasion. It needed to come off its hanger.

By Margaret Hale, Travel & Lifestyle Editor
Updated · 10 min read

Read to the end: #1 is the one outfit that puts saved clothes back into your week when you lay it out tonight.

There was a red coat on the back of the closet door, still buttoned on its hanger. The good occasions came and went. So did the ordinary Tuesdays when it would have looked terrific. It stayed there because wearing it seemed to require a reason. By winter's end, the hanger had seen more of it than anyone else had.

Here are 23 things worth wearing before another Tuesday passes.

23The Red Coat

A red coat fills the middle of a city sidewalk scene as a woman over 60 waits at a bus stop with a grocery bag.

A red wool coat is hard to miss at a bus stop.

You bought it for an occasion, then decided each occasion wasn't quite enough. That bright wool looks just as good beside a grocery cart. A coat doesn't know where you're going. You do, though, and for years that meant checking the invitation before reaching for it.

The first trip needn't be memorable. Think of the hardware store, the library, or the walk to pick up a prescription. Nobody at the counter knows which day you saved it for. The coat still keeps you warm.

Wear it on an errand this week, without changing anything else.

22The Sleeveless Dress

A sleeveless dark cotton dress is centered on a woman over 60 reaching for a glass in her home kitchen.

Bare arms show up clearly against a dark sleeveless dress.

For years, the rule was to cover them after a certain birthday. Who set it? A cotton dress with room through the shoulders feels better in August than a cardigan worn out of duty. The armhole matters more than the age of the arm: it should sit close enough to keep your bra covered.

Try the dress on, raise both arms, and keep it if you can move freely.

21White Jeans After September

White jeans are centered on a woman over 60 walking through a leaf-covered park in a navy sweater and boots.

White denim stands out beside a row of dark winter coats.

The old Labor Day rule outlived its usefulness. Thick white denim works with a navy sweater and boots when the weather turns cold. Thin summer denim is another story; the fabric, not the calendar, makes the difference.

Put the white jeans beside your winter shoes and see what works.

20A Pair of Flat Sandals

Flat leather sandals are centered on the feet of a woman over 60 crossing a tiled café floor.

Flat leather sandals leave both feet firmly on the pavement.

A heel was once treated as the price of looking dressed. Then came the evening spent searching for a chair. A flat sandal looks deliberate when its straps hold your foot securely. Check the sole, too: smooth leather slips on wet tile. Comfort is no favor if the shoe slides off before you reach the door.

Walk across the shop floor twice before buying a pair.

19The Wide-Leg Trousers

Wide-leg trousers are centered on a woman over 60 walking across her living room in her usual shoes.

Wide trouser legs move separately as she crosses the room.

You didn't need to earn room in your clothes. Look for a waistband that stays put when you sit, then check where the hem falls over your shoes. Too much fabric at the ankle gets underfoot.

Try a pair with the shoes you actually wear, then sit down.

18A Black Turtleneck

A black turtleneck is centered on a woman over 60 standing by her kitchen window in daylight.

The black knit frames her face against the kitchen window.

Some women were told black near the face looked severe. A turtleneck also solves the cold-neck problem without a loose scarf in the way.

The useful test is the collar: it should turn your head without tugging at your throat. Wool is warm but scratchy for some skin; cotton or a smooth knit gives you another choice.

Wear it for a full afternoon at home before deciding whether the collar stays.

17The Silk Scarf

A silk scarf is centered at the collar of a woman over 60 drinking coffee at her kitchen table.

A silk scarf sits loosely over the collar of her shirt.

You saved it because the silk felt too good for an ordinary day. A short scarf tied once stays clear of soup and purse straps. That hand-rolled edge looks better in motion than folded in a drawer.

Tie yours over a plain shirt tomorrow, then leave the house.

16The Oversized White Shirt

An oversized white shirt is centered on a woman over 60 rolling up its sleeves beside a bedroom mirror.

The white shirt hangs past her hips, sleeves pushed up.

It belonged to the category of clothes you admired on other women. The trick is choosing where the extra cloth goes. Broad through the body gives you movement; shoulders that drop too far pull the sleeves into your hands. Cotton poplin creases, and that's part of wearing it rather than storing it.

Try one over straight pants, and roll each cuff above your wrist before judging the fit.

15A Pair of Bright Sneakers

Bright yellow sneakers are centered on a woman over 60 walking along a gray neighborhood sidewalk.

Yellow sneakers interrupt the gray sidewalk and her black pants.

The pair was bought for walking, then kept out of sight under longer trousers. There was no rule against seeing your shoes. A clean pair in a color you love makes the walk to lunch look like part of the day, not a chore before it. You don't have to dress everything else around them.

Start with the clothes already by the door. Let the yellow show below a skirt or at the hem of black pants. If you like the look, leave the longer trousers in the closet.

Wear them with a skirt once, even if you expect to change.

14The Denim Jacket

A faded denim jacket is centered on a woman over 60 reaching across a kitchen table.

The denim jacket has faded at the elbows and cuffs.

Perhaps you wore one for years, then decided it belonged to a younger woman. Denim has no age limit, but a stiff collar or tight upper arm can ruin the reunion. The old jacket you kept has already softened where your body moves. That matters more than whether its wash matches your jeans.

Pull yours from the closet, put it over a dress, and check whether both arms reach forward easily.

13A Full Midi Skirt

A full midi skirt is centered on a woman over 60 coming down the stairs at home.

The full skirt sways below her knees on the stairs.

You were told it would make you look too dressed up for daytime. Cotton, denim, or a soft wool blend changes that. The real nuisance is a waistband that twists when you walk, not the amount of skirt.

Take it up and down a staircase before cutting off the tags.

12A Leopard-Print Blouse

A leopard-print blouse is centered on a woman over 60 standing between two plain black jackets hanging in her bedroom.

The leopard-print blouse sits between two plain black jackets.

Animal print spent years being called too loud or too much. Small brown-and-black spots read differently from a head-to-toe costume. A blouse lets you see the print beside clothes you already own. If the fabric clings or the neckline bothers you, skip it; the permission is to wear what you like, not to endure a bad shirt.

Put the blouse on with your oldest black pants and look in daylight.

11Gold Hoops in Daylight

Gold hoops are centered on a woman over 60 seen from the side as she pours coffee at home.

Gold hoops catch the light while she pours coffee.

The jewelry box held them for dinners that kept getting postponed. Small or large, hoops belong to the morning, too. Check that the clasp closes fully and the weight doesn't pull at your ears; an earring that hurts won't become comfortable through determination.

Wear the pair through breakfast first, then decide whether it stays on.

10A Jumpsuit With Pockets

A jumpsuit with pockets is centered on a woman over 60 reaching into a kitchen cupboard.

The jumpsuit hangs in one clean line from shoulder to ankle.

It looked like too much of a statement on the hanger. On your body, the question is practical: can you sit, reach, and use the bathroom without a struggle? Pockets help, but only if they lie flat when filled. A waist tie should meet your actual waist, not the one the maker imagined.

Try it in a fitting room with a door, and practice getting out of it before you decide.

9The Short Haircut

A short haircut ending above the collar is centered on a woman in her sixties seen from the side by a daylight window.

The hair ends above her collar, clear of her earrings.

Long hair wasn't the price of looking feminine. Short hair isn't a requirement, either. But if you kept the same length to avoid comments, that's a poor reason to keep it. A cut with shape around the ears grows differently from a blunt chop.

Tell your stylist, “I want to see my earrings,” and discuss the back before any scissors move.

8A Bold Red Lipstick

Bold red lipstick is centered on a woman over 60 smiling at her kitchen table beside a window.

Red lipstick draws the eye straight to her smile.

Maybe someone once called it too much for daytime. That was their opinion, not a dress code. The useful question is whether the color looks right to you in natural light. A pencil along the lip edge gives a crisp border; blotting with tissue takes away the excess before it reaches your teeth. You needn't save that careful line for dinner.

Try the shade by a window, and wear it to buy milk.

7The Leather Jacket

A creased leather jacket is centered on a woman over 60 picking up her keys near the front door.

The leather jacket is creased at the elbows from use.

It wasn't waiting for you to become a different woman. A close-fitting jacket works only when it closes without pulling across your back. Try it over the thickest shirt you'd wear underneath. If the shoulders fight you, no amount of confidence fixes the cut. If they don't, stop treating it like a costume.

Wear it over the clothes already hanging by your door.

6A Pair of Tall Boots

Tall boots are centered beneath the wool skirt of a woman over 60 walking across a hardwood floor.

Tall boots rise to the knee beneath a wool skirt.

Perhaps you worried they looked too bold, or that skirts were required. They aren't. A shaft that pinches your calf gets worse as the day goes on; a gap wide enough for a hand changes the shape entirely. Test the zipper while seated, and walk on a hard floor to hear what the heel does.

Keep the pair that lets you take a normal stride, not the pair that wins in a mirror.

5The Linen Pants

Wrinkled linen pants are centered on a woman over 60 sitting at an outdoor café table.

The linen pants wrinkle across her lap at the café.

That crease is what linen does when you sit down. It doesn't mean you chose badly or failed to dress properly. Loose linen lets air move on a hot day, but pale fabric needs a check for transparency. Look at it against daylight, not only the dressing-room mirror.

Wear the pants for lunch, and let them come home wrinkled.

4The One-Shoulder Top

A one-shoulder top is centered on a woman over 60 reaching for a glass at a dinner table.

One bare shoulder shows above the table at dinner.

It wasn't reserved for a younger guest. What matters is whether the neckline stays put when you reach for a glass. Some tops need a strapless bra; others have enough structure to wear with the support you prefer. Test that at home before committing to an evening of adjusting fabric.

Raise your arms, bend forward, and sit down in it. If it stays where you put it, make a plan to wear it.

3The Colorful Swimsuit

A bright blue swimsuit is centered on a woman over 60 walking toward the water at a beach.

The blue swimsuit is bright against the sand and water.

For years, the swimsuit decision was tangled up with being seen. You were going to swim, not ask the beach to grade your body. Look for straps that stay on your shoulders and leg openings that don't ride up after a few steps.

Put it on before the trip, move around the house, and pack the one that holds its place.

2A Dress With Big Pockets

A dress with big pockets is centered on a woman over 60 with both hands tucked into them in her kitchen.

Both hands disappear into the pockets of her dress.

You were handed plenty of clothes that expected you to carry everything elsewhere. Real pockets hold keys and a folded tissue without pulling the skirt out of shape. Slip your hands in and check the lining; shallow pockets are decoration with extra seams. A dress that works while you're moving deserves more than a special-event hanger.

Wear it on a regular day and put something in those pockets.

1The Skirt and Blouse You Already Own

A plain skirt and blouse lie together in the middle of a made bed as a woman over 60 selects earrings and shoes nearby.

A plain skirt and a good blouse lie side by side.

No purchase solves a closet full of clothes you've been saving for permission. This skirt and blouse haven't gone anywhere together yet, though both fit. Choose the shoes and earrings you want to wear with them. Put everything where you can see it. Morning gives the clothes you've laid out a fair chance against your usual rush.

Choose that unworn combination tonight, and give it an ordinary place to go tomorrow.

The bottom line

All 23 share the same obstacle: waiting for a day important enough to justify wearing them.

You already know a Tuesday counts. Put the clothes on before you talk yourself out of them. Which one have you kept in your closet?

Bonus: The Skirt and Blouse You Already Own

  1. Pull out the skirt and blouse you've kept apart, and lay them together on the bed.
  2. Add shoes and something warm enough for tomorrow's weather.
  3. Try the whole outfit on tonight; sit, walk, and reach.
  4. Change what doesn't work, then leave the finished outfit where you'll see it in the morning.

Margaret Hale

Travel & Lifestyle Editor

Margaret has covered travel for 25 years and has ridden every long-distance train route in the U.S. at least once.