What to Wear in Your 30s, 40s, 50s, 60s

We've all been there: gazing at a store window and wondering, Could I wear that? The answer is, maybe. Every season the racks are filled anew, and nailing your chicest look is all about selecting the right pieces at the right time. Luckily for you, we've done the editing. Here's your shopping guide to help you get your style right at every age

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Tropical prints in your 30s

Bold blooms, short skirts, funky accessories.

Soludos X We Are Handsome cotton and jute espadrilles, $65; soludos.com

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Choose flats with flair

For those moments when you give heels a rest, these are go-with-alls.

Kate Spade leather and rubber sandals, $198; katespade.com.

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Don't be shy

Novelty pants (industry-speak for slacks with exotic prints, like these) are all the rage and a fun way to experiment with pattern or color (or both). Bottom heavy? Skip them.

Banana Republic print pants, $90; banana​republic.com.

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Size down

Ah, it's nice to be young and able to carry just the essentials. When you're BRG (before reading glasses), a tiny clutch is all you need.

RAFÉ straw and mother-of-pearl clutch, $225; Bloomingdale's.

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Have fun with trends

Now is not the time for subdued neutrals; now is the time for tongue-in-cheek whimsy. For those blessed with great legs, this scalloped-hem skirt is one mai tai away from a good time.

Cynthia Rowley bonded spandex skirt, $225; cynthiarowley.com.

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Funkify your shades

You've been rocking your aviators for a few years now, but trust us, change is good.

Silvano sunglasses made from recycled skateboard decks, $125; silvanoapparel.com.

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Save on accessories

This Tahitian-inspired fringed neckpiece packs style bang for your buck; we love its earthy feel.

Kate Spade Saturday leather and silk-thread necklace, $50; saturday.com.

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Layer with prints

When cool weather calls for a topcoat, skip the same old, same old and instead opt for this fantastic photo-printed version.

425 Fifth cotton double-weave jacket, $248; lordandtaylor.com.

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Embrace femininity

You're still at a stage when you can pull off something girly without looking silly. Case in point: this blooming T-shirt, which will provide the pretty for your boyfriend jeans.

Eva Franco embroidered ponte top, $270; evafranco.com.

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Don't be so serious

Save yourself from a black-pump slump and instead take a walk on the wild side.

Rebecca Minkoff leather pumps, $275; rebeccaminkoff​.com.

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Go big or go home

It takes youth and chutzpah to wear a statement print, and the way we see it, you've got both. Nothing beats the ease of a shirtdress, and this is the young, zany version you need.

French Connection sleeveless dress, $168; usa.frenchconnection.com.

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Get girly

A pale pink skirt gets a cool assist from an edgy, exposed black zipper.

Sonia by Sonia Rykiel stretch polyethylene skirt, $350; 516-374-1054.

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Bling it up

Because sometimes more is more—whether a choker with drama or a wristful of fun.

Shop Design faux-leather necklace with metal, $32; shopdesignspark.com. Gypsies and Debutantes woven bracelets with vintage Czech crystals, $78 each; gypsiesand​debutantes.com.

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Frame your face

When you need an anchor for all the loud floral prints, this top will do it (with the bonus of a delicate, textural neckline). You're welcome.

Tory Burch sweater, $350; Saks Fifth Avenue.

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Sporty styling in your 40s

Color blocking, silver accents, stripes.

DKNY neoprene coat, $1,200; dkny.com for stores.

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Upgrade your T-shirt

Consider this the decade of better basics. A simple topper gets amped up with color blocking and visually slims your midsection. If that's of interest.

NYDJ color-block tee, $69; nydj.com.

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Drench yourself in color

If your wardrobe mostly spans the spectrum from black to gray (ahem), it's time to reboot. This dress is comfortable enough for errands but polished enough for drinks with friends.

Eileen Fisher silk crepe de chine dress, $258; eileenfisher.com.

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Make casual tops count

Rather than reaching for that boring sweatshirt (or, dare we say, one of your husband's college has-beens), grab this perforated-front beauty and give your weekend look a reinvention.

Vince Camuto faux-leather top, $84; vince​camuto.com.

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Schlep in style

Between your work files, your kids' soccer duds and whatever else you tow around every day, you deserve a snazzy tote. This one is as light as a feather and features a zip top.

MZ Wallace oxford nylon tote, $195; mzwallace.com.

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Brighten up

No, you really don't need another pair of khakis; instead, wake up your legs with these orange tux-striped chinos.

Tommy Hilfiger cotton blend pants, $299; 212-223-1824.

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Bring sexy back

You may not be rocking the exact body of your twenty-something self, but this will prove you've still got it. Hold the hose, cue the stilettos.

Club Monaco polyester and leather skirt, $150; clubmonaco.com.

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Step away from dainty

Your trusty tank watch has served you well for many years, but it’s time (pun intended) to have more fun.

Guess chronograph watch in stainless steel, $160; guess​watches.com.

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Incorporate texture

Haul it all, whether you're headed to the office or the playing field.

Botkier vegan-leather tote, $195; botkier.com.

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Make room for new flats

The slip-on sneaker is a huge spring trend, and we likey. This silver version is more grownup than, say, a plaid or floral print.

Dolce Vita leather sneakers, $139; dolcevita.com.

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Put the cool in casual

Basics get a boost from great design. We’re mad for vests (an extra layer for warmth and interest), especially ones with useful details like pockets and zippers.

Rebecca Minkoff vest, $298; 866-838-6991.

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Sneak in the shapewear

Yes, the control panels are built right in. Best. Pants. Ever.

Lisette L rayon blend pants, $118; lisette-l.com.

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Play peekaboo

Layer this camisole under a jacket or cardi for a surprise hit of color. Don't want to go braless? That's what a strapless is for.

By Chance silk cami, $198; bychancebydesign.com.

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Go bare

If you've been dreaming of a flat, comfortable, indestructible sandal, your wish has come true. This is white done right.

Nine West ankle-strap jelly sandals, $49; zappos.com.

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Basic is better

Best in dress? This one. Wear alone or over leggings.

Loft color-block T-shirt dress, $90; loft​.com.

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Graphic pattern in your 50s

Structured shapes, minimal jewelry, unexpected details.

CH Carolina Herrera floral dress, $610; 310-276-8900.

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Dare to be bold

The delicate prints, the washed-out colors—give them a rest and re-energize with the season’s print trend. This dress  will transport you to your happy place in an instant, leaving all those little black dresses cowering in a corner.

Trina Turk polyester dress, $288; trina​turk.com.

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Rethink your shoes

Proof that you don't have to sacrifice style for comfort, these wedges are lower than they look. They're open toed, which means you'll want to leave your hose in the drawer.

Coye Nokes ankle-strap wedges, $250; coyenokes.com.

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Step out of the box

The playful pattern of these pants will beg you to kick up your heels (or flats, your choice).

Chico's polyester ankle pants, $89; chicos.com.

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Add the unexpected

Our fashion team fell hard and fast for this floral cross-body bag and especially liked it against all the graphic black and white.

Tory Burch leather messenger bag, $435; toryburch.com.

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Mix in some small scale

Any time you reach for one of the dozen basic-black crewnecks stacked in your closet, consider this instead; the small-scale geometrics give it a little more oomph, but you can wear it with just as much. Feeling particularly daring? Pair it with a black-and-white floral skirt.

J. Jill rayon blend top, $69; jjill.com.

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Go all the way

Nothing beats a frock for the ease of one-and-done dressing. What we love here: serenity up top, a party down below.

Talbots cotton sateen sheath, $189; and leather belt, $40; talbots.com.

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Invest in a showstopper

Turn up the style volume on anything and everything in your wardrobe with this light-weight coat. The perforated fabric lets in the light—and also a breeze or two. Yes, it's expensive, but (a) it looks it, and (b) you'll wear it for years to come.

Clover Canyon grid neoprene coat, $660; clover​canyon.com.

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Retire your LBD

The artful print, phenomenal fit and ideal length (to the knee) make this a winner.

Angelys Balek satin crepe dress, $440; effiesinc.com.

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Hit the snooze button on studs

All eyes on you: These attention-getting earrings are so versatile, you can wear them every day.

Dinosaur Designs resin earrings, $205; dinosaurdesigns.com.

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Update your classics

Once you try a coated canvas tote, you'll never look back. Our advice? Keep calm and carry a fabulous bag.

Peter Pilotto cotton tote with PVC coating, $40; target.com.

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Don't play it safe

Bold is beautiful! The tunic's longer length is ideal for today's untucked look, whether you pair it with a skirt or skinnies.

Coldwater Creek polyester blend top, $80; coldwater​​creek.com.

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Pump up the volume

Sexy, stylish and in a scheme that's surprisingly neutral.

Banana Republic floral pumps, $128; bananarepublic​.com.

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Hike your hemline

The black-and-white blocking visually slims your lower half, while the kicky zipper leaves a little—or a lot—to the imagination.

Worthington zipper-front skirt, $36; jcpenney.com.

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Soft neutrals in your 60s

Subtle shine, luxe fabrics, statement accessories.

Etienne Aigner pleated skirt, $345; etienneaigner.com.

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Try blush instead of white

The soft hue glows against skin and goes with everything. The weight of this V-neck is whisper thin, and the shape is roomy—wear it with gray, khaki or white.


Minnie Rose cashmere sweater, $255; minnierose.com.

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Update your everyday dress

The loose, draped style is wearable but still polished and can easily be topped with a cardigan if you desire. Pair with a bag that has a little texture (woven) and metallic shoes for a soupçon of shine.

Halston Heritage boatneck dress, $325; halston.com.

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Try on-trend sandals

All the stability of a sturdy sole but with fashionable details and chic silver accents. Please note: A pedicure is not optional.

Nanette Lepore sandals, $348; nanettelepore​.com for stores.

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Gone are the days of carting around every little thing you can think of, and be thankful that you can actually travel light again. Can't break your tote habit? Stow this beauty inside, then remove it to hold on to your essentials while you park your big bag at coat check.

Loft foldover clutch, $45; loft​.com.

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Modernize your jewelry

Warm gold and earthy materials (stone) look just right with all the soft colors here. Wear this alone or stack with other gold bracelets.

Kara Ross gold bangle with mother-of-pearl resin and rock crystal, $150; kararossny.com

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Class it up

A luxe-looking shirtdress provides comfortable coverage and is as dressy as you ever need to be.

BCBG​-Max Azria georgette dress, $248; bcbg.com.

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Surprise them

It's hard to overlook the comfort of a knit. The single one-strap shoulder provides the wow factor in this ideal weekender.

Eileen Fisher dolman top, $238; eileen​fisher.com.

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Experiment with shapes

Want to look modern? Embrace subtle style updates. The shape of this bag is what's new, thanks to high-design inspiration.

Calvin Klein spazzolato-leather bag, $428.

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Add an edgy detail

Your jewelry doesn't have to be so precious. Baubles with leather accents are all the rage and so cool, you'll instantly look a decade younger.


Earthy Chic leather wrap bracelet with snake, $68.

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Add an edgy detail

Sure, you want to look great, but not at the expense of comfort. With the right accessories, a simple A-line dress such as this one will make you look and feel your absolute best. You can even skip the shapewear and use one of your full slips to keep it from clinging.

Elk rayon blend dress, $135; elkaccessories.com. Chico's cording necklace with metal pendant, $45; chicos​.com.

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Play with accessories

If you want a hip heel, try the on-trend open toed bootie.

Elliott Lucca leather booties, $149, elliottlucca.com.

Mix in some pattern

Whether on a pencil skirt or loose pajama-style pants, a print done in neutrals is easiest to incorporate.

Nic + Zoe cotton and spandex skirt, $128. Ann Taylor pants, $98; anntaylor.com.

Next: New Fashion Dos and Don'ts

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First published in the March 2014 Issue

Share Your Thoughts!


Joanne 04.25.2014

Why the bland neutrals for the over-60 crowd? The feature in the March issue was a real disappointment. Of all people, Goldie Hawn was chosen to represent us. Not a woman who seems to be comfortable with aging. Then, the clothes were all relentlessly BORING versions of beige and brown. Certainly not a very lively or engaging way to dress.

Harise Poland04.24.2014

I have tried more than once to find the items you show in one of these lists, in the store that is shown, using the link provided and it is not among the offerings from that store. it would be helpful if the link actually went to the actual item on the store's site. plus the exact name isn't given so I don't know exactly what to search for. are these items really available at jcp.com for example? or is it just a way to get more customers to click. this happened on a jewelry site as well. where is that rock crystal bangle? where is that zip front skirt?

kathleen 04.24.2014

the clothes you showed are soo expensive for the average woman-maybe 4 items less than $100-Please show us fashions that are more reasonably priced-IMO this would be greatly appreciated to all.

kathleen 04.24.2014

the clothes you showed are soo expensive for the average woman-maybe 4 items less than $100-Please show us fashions that are more reasonably priced-IMO this would be greatly appreciated to all.

kathleen 04.24.2014

the clothes you showed are soo expensive for the average woman-maybe 4 items less than $100-Please show us fashions that are more reasonably priced-IMO this would be greatly appreciated to all.

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