The Biggest Outfit Mistakes for Women Over 50

Time to give clothes that are too revealing, ill-fitting or plain old uncomfortable the boot

Lois Joy Johnson,

AARP

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Published January 09, 2026

a collage with models wearing outfits and icons with checks and x marks to indicate whether the fashion choices are correct

(From left) Lane Bryant Ponte Twill Tie-Waist Long-Sleeve Dress in Black; Chico’s Collared Denim Trim Cardigan in Caramel Apple Heather; Banana Republic Factory Women Velvet Off-Shoulder Top in Douglas Fir

AARP (Shutterstock, Getty Images, Lane Bryant, Chico’s, Banana Republic Factory)

“Sorry, but designer logos make me feel rich!”

“Are jeans and a tee too underdressed for this?”

“Why do my classic clothes feel frumpy?”

“Are low Vs and clingy pants tacky over 50?”

sharon stone, jennifer lopez, garcelle beauvais and tracee ellis ross wearing questionable red carpet looks

(From left) Even fashionable celebrities like Sharon Stone, Jennifer Lopez, Garcelle Beauvais and Tracee Ellis Ross make occasional wrong turns.

AARP (Getty Images, 4)

We’ve all had that great moment when an outfit made us feel slimmer, sexier, more stylish and confident. We’ve also had times when what we wear feels too tight, too casual, too trendy, stuffy, outdated, overdone, too big, baggy or boxy. Those outfits bashed our self-esteem, wrecked our comfort and made us squirm with embarrassment until we got home. Here are the most common mishaps — and and how to avoid them.

a collage with models wearing a blue button down shirt, a pleated leather skirt and a pair of fitted black trousers

(From left) Nine West Women’s Drapey Button Down Shirt in Resolute Blue; Madewell Women Pleated Midi Skirt in Dark Chicory; Lane Bryant Ponte Pull-On Straight Pant in Black

AARP (Kohl’s, Madewell, Lane Bryant)

1. The mistake: skintight clothes go too far

So, you love skinny jeans, bodysuits, leggings and stretch tops?

A body-positive attitude is great, but there’s a difference between proudly displaying your body and betraying it. Are you flaunting a voluptuous silhouette, or are you just drawing attention to a tummy bulge and back fat? Are you boasting a newly firm shape or simply strutting a slim, albeit a bit flabby, one? Wearing formfitting outfits can be a payoff for losing weight, sticking to an exercise regimen or regaining your mojo, but too much of this good thing can be just plain tacky.

The solution: Unless you’re onstage in Cirque du Soleil, headlining a show in Vegas or nominated for a Golden Globe, avoid a head-to-toe skintight look. Don’t wear skinny jeans with a fitted stretchy top. It offers too much information. Save the big reveal for swimsuit season. Instead, try body-skimming clothes that leave something to the imagination, such as straight jeans and relaxed tops that accentuate your shape. If you’re truly stuck on serious flaunting, at least elevate the look by pairing a formfitting piece with a looser one.

Try a close-to-the-body top, like the Gap Stretch Jersey Scoopneck Top in Black ($10, gapfactory.com), paired with an A-line skirt, such as the Madewell Women Pleated Midi Skirt in Dark Chicory or Black ($148, madewell.com). Or add the figure-revealing Lane Bryant Ponte Pull-On Straight Pant in Black ($35, lanebryant.com) to a relaxed tee, like the Banana Republic Women Relaxed Cotton Boat-Neck T-Shirt in Red Stripe or Navy Blue ($100, bananarepublic.gap.com). They’ll get the message.

a collage with a model wearing black leather cropped trousers, a brown rib knit top paired with a gold necklace, and a model wearing a black and white ensemble

(From left) A New Day Women’s Faux Leather Sailor Pants in Black; Gap Factory Women Bell Sleeve Boatneck T-Shirt in Dark Brown; Chico’s Faceted Gem Drop Off Bib Necklace; Aqua Satin Button-Front Blouse in Black

AARP (Target, Gap Factory, Chico’s, Bloomingdale’s)

2. The mistake: showing up overdressed or underdressed

“I wish I could go home and change my clothes.”

Have you ever said this? It happens. Sometimes your idea of “dress casual,” “casual chic” or “creative cocktails” is either too laid-back or too glammed up. When you’re in jeans or athleisure wear and everyone else is in cocktail party clothes — or vice versa — it’s time for a dress code reset.

The solution: Always take a dress-to-impress approach. No matter how casual or dressy, err on the dressier side. One of the most foolproof looks is to wear black pants and a black top. Sounds simple, but this gives you a polished, slim base that’s fashionable day or night. By styling it up or down, you control the level of dressiness.

For example, black denim jeans and a black boatneck tee are not as dressy as faux leather pants with a black silky blouse or cashmere sweater. When the dress code is uncertain, always pair a basic piece with an elevated one. Wear a black tee, like the Gap Factory Women Bell Sleeve Boatneck T-Shirt in Black ($16, gapfactory.com), with upscale black leather pants, like A New Day Women’s Faux Leather Sailor Pants in Black ($45, target.com); or a sophisticated satin blouse, like the Aqua Satin Button-Front Blouse in Black ($78, bloomingdales.com), with basic black jeans, like the Gap Women High Rise 90s Slim Straight Jeans in Black Wash ($53, gap.com). Then, depending on your style and taste, add one statement accessory. A wow necklace, like Chico’s Faceted Gem Drop Off Bib Necklace ($67, chicos.com), or metallic shoes, like the Bella Vita Kimiko Ballet Flat in Champagne Leather ($100, dsw.com), is really all you need. It’s better to receive compliments or appreciative second glances for your style than to get a side-eye for lacking it.

a collage with models wearing a brown knit ensemble with wide leg trousers, a brown midi skirt and a blue and black striped button down top

(From left) Vince Camuto Women’s Pull-On Wide Leg Pants in Nude; Woman Within Plus Size 7-Day Knit A-Line Skirt in Chocolate; Madewell Women Straight-Hem Shirt in Poplin in Riviera Coast.

AARP (Macy’s, Kohl’s, Madewell)

3. The mistake: looking chic but feeling uncomfortable

“I can’t sit in this.”

“These shoes are killing me!”

“I think my bra is showing.”

Sound familiar? Never choose fashion over comfort. If what you’re wearing doesn’t feel good, it shows up in your body language and facial expression. Do yourself a favor and skip anything that feels tight, itchy, scratchy or just plain annoying. Common complaints include extreme shapewear; high heels and pointy-toe shoes that pinch; clingy pencil skirts and those with a too-high slit that make walking and sitting a chore; jeans with a rise that’s too high or too low; sheer blouses and tops that make bulges when tucked in; and heavy dangly earrings that stretch pierced lobes.

The solution: First, give your wardrobe some tough love and donate anything that makes you fuss, fidget or complain. Do a test run and wear any clothing piece or shoe you’re on the fence about for a home-alone day. Try walking, sitting, crossing your legs, climbing stairs, reaching for something and crossing your arms. Many women over 50 say they have “home” clothes and never wear their “away-from-home” or “going-out” outfits until the day of the outing or event.

Look for stress-free swaps like stylish flats with roomy almond or square toes, such as the Vionic Orinda Flat in Dark Brown Leopard Print, Black or Tan Leather ($105, dsw.com). Opt for comfy, elastic-waist, pull-on skirts and pants, like the Woman Within Plus Size 7-Day Knit A-Line Skirt in Medium Heather Gray, New Khaki, Toffee, Black or Chocolate ($36, kohls.com) or Vince Camuto Women’s Pull-On Wide Leg Pants in Rich Black or Nude ($109, macys.com), that ease weight fluctuations and bloat; and not-too-short, not-too-long tops like the Madewell Women Straight-Hem Shirt in Poplin in Riviera Coast ($98, madewell.com) that end at the hip and can be easily worn untucked or semi-tucked.

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a collage with a model wearing a black leather midi skirt, a model wearing navy blue cropped trousers with gold tone buttons and a model wearing a knit cardigan with a double breasted lapel

(From left) June & Vie Women’s Plus-Size Paneled Faux Leather Midi Skirt in Black Onyx; Chico's Emme Sailor Straight Crops in Passport Blue; Nic+Zoe Elegant Knit Blazer in Sugar Cookie.

AARP (Macy’s, Chico’s, Bloomingdale’s)

4. The mistake: an outfit’s fit is all wrong

Do your midi skirt hems stop at the widest part of your calves? Are your jacket sleeves hiding your hands? Do your new wide-leg pants crease and puddle over your shoes? Are your boxy “boyfriend” blazers and overdone oversized sweaters making you invisible? If the answers are “yes,” you need a new full-length mirror and a tailor/seamstress ASAP.

Anything that’s too long, boxy, baggy or shapeless is an outfit breaker and makes even the most fashionable clothes look sloppy. No matter how trendy or expensive a skirt, jacket or pants, clothes that don’t fit your proportions need a fix or a return. Give your clothes the personalized tweaks your body deserves.

The solution: Get picky about fit. Midi skirts and dresses should hit just above or below the widest part of your calf, not sit at it (this makes your legs appear wider and shorter). Long, full-length pants should hover over your shoes and not hide them or puddle (dirty hems are never stylish). Ankle pants should end at or above the anklebone. Blazers, coats and jackets should cover your wristbone, not your hands, when your arms are straight down; shoulder pads should look realistic, not hulky.

Haul all new buys, and even old clothes you wear regularly, to the tailor. Often, just getting skirts, pants and jeans hemmed, and jacket sleeves snipped to the right length for your proportions, makes a huge difference in how you look. It’s worth the expense.

Check out the fit of the June & Vie Women’s Plus-Size Paneled Faux Leather Midi Skirt in Black Onyx ($94, macys.com), the Nic+Zoe Elegant Knit Blazer in Sugar Cookie or Dark Indigo ($198, bloomingdales.com) and Chico’s Emme Sailor Straight Crops in Passport Blue ($110, chicos.com) for some visual guidance.

a collage with models wearing four different styles of belted midi dresses

(From left) Sonoma Goods for Life Women’s Three-Quarter Sleeve Midi Dress in Dark Blue Stripe; Universal Thread Women’s Puff Elbow Sleeve Midi Shirtdress in Black and Blue/Orange Floral; Lauren Ralph Lauren Plus Size Twill Point Collar Midi Shirt Dress in Navy/Cream Multi.

AARP (Kohl’s; Target, 2; Macy’s)

5. The mistake: feel-good dresses that add extra pounds

Almost every woman I meet, no matter how confident, still looks in the mirror and says, “Does this make me look heavier?” Even worse, when trying on a loose dress, she says, “Does this make me look fat?” The frank answer: sometimes, yes.

Let’s address the fashion elephant in the room: the trend toward voluminous dresses that feel great and hide bellies and jiggles but lack body definition. Learn to benefit from the ease, but understand how to manage it to your advantage.

The solution: The secret, regardless of your shape and size, is to always hint at body definition. When it comes to voluminous dresses, that often means adding a belt to loose styles, or choosing dresses that come with a self-tie.

Before you say, “No, that makes my belly bulge,” hear me out. A self-tie or a narrow belt, like the J.Crew Factory Women’s Skinny Leopard Calf Hair Belt in Leopard Suede ($30, factory.jcrew.com), can control volume in a flattering way, with no belly bulge. The trick is to position the belt or tie just above your real waist on your ribcage, not at the fuller circumference of your belly. No need to cinch; even a subtle indent does the trick.

When shopping, look for midis or maxis (the length helps balance the volume) like Sonoma Goods For Life Women’s Three-Quarter Sleeve Midi Dress in Dark Blue Stripe, Tonal Plum Leaf or Ivory Berry Spritz ($45, kohls.com), Lauren Ralph Lauren Plus Size Twill Point Collar Midi Shirt Dress in Navy/Cream Multi ($225, macys.com) or Universal Thread Women’s Puff Elbow Sleeve Midi Shirtdress inBlack or Blue/Orange Floral ($42, target.com). And yes, just cut off any belt loops first (or have a tailor do it) that can get in the way of belt/tie placement.

a collage with a faux fur swing coat, a white flower hair accessory, a navy blue handbag and a model wearing a brown and blue collared knit cardigan

(From left) Ann Taylor Satin Rosette Brooch in White; Echo Collarless Faux Fur Jacket in Silver; On 34th Jynna Glazed Baguette in Rainstorm Blue Glaze; Chico’s Collared Denim Trim Cardigan in Caramel Apple Heather.

AARP (Ann Taylor, Bloomingdale’s, Macy’s, Chico’s)

6. The mistake: vintage clothes are appealing but they don’t love you

Women often say things like:

“I’m so glad I saved these pants; they’re back in style!”

“It’s a 1985 Donna Karan!”

“I always looked good in neon green!”

This happens when back-of-the-closet oldies get rejuvenated without really considering whether they still work for your life, body, skin tone and style.

The solution: Comeback clothes and accessories have a history, but not every one is a keeper. For example, those wide-leg pants? You don’t need the belly-emphasizing pleats and leg-shortening cuffs of your oldies. Power blazers? Sorry, but smaller, more natural shoulders or small shoulder pads are better. And neons? They’re often too harsh to flatter mature skin tones.

So what does work? Vintage accessories and basics such as cardigans are the easiest way to add personality to your outfits without a dated or costume-like effect. Stick to one item at a time. The best revival pieces right now are ’90s-style “baguette” bags and chain-strap quilted bags that can be worn as crossbody slings; printed silk scarves; statement jewelry such as cuffs, brooches, one-of-a-kind necklaces and bold earrings; kitten heels and slingbacks (make sure those toes are not pointy pinchers!); faux fur jackets; and twinsets.

That said, if you love a vintage look, you can also try updates with new features, like the On 34th Jynna Glazed Baguette in Rainstorm Blue Glaze or Black Glaze ($80, macys.com) with shoulder and crossbody straps; the Echo Collarless Faux Fur Jacket in Silver ($129, bloomingdales.com), lightweight with comfy raglan sleeves; Chico’s Collared Denim Trim Cardigan in Caramel Apple Heather ($150, chicos.com), a mix of casual and classy; or the Ann Taylor Satin Rosette Brooch in White ($45, anntaylor.com), a minimalist’s idea of embellishment.

a collage with two different styles of maxi length animal print dresses, a gray felted jacket and a brown leather shoulder bag

(From left) H&M Women’s Tie-Belt Shirt Dress in Beige/Leopard Print and Cream/Zebra Print; Madewell Women Double-Faced Cropped Chore Jacket in Light Heather Gray; Mango Women Suede Shoulder Bag With Stitching in Brown.

AARP (H&M, 2; Madewell; Mango)

7. The mistake: overdoing logos and obvious branding

Are you a brand snob? Let’s be honest, many women do love a status symbol, logo or item. For them, the initials or a specific look-alike item (counterfeit luxury goods are illegal, but imitations persist) convey a certain aesthetic that hints at taste and wealth, validating the item and giving their self-confidence a boost. Nothing wrong with that idea in general, but when chasing logo-this and logo-that becomes your outfit goal, it can have the opposite effect.

The solution: Wear a maximum of two “showy” logos at a time. A recognizable branded bag or a signature belt oftentimes gives low-cost clothes just enough oomph. Also try getting into “quiet luxury.” This category of fashion brands whispers its sophistication rather than shouts it. You’ll get posh fabrics, tasteful contemporary designs and the upscale neutral colors that elevate your wardrobe without disrupting your budget.

Check out Banana Republic, Mango, H&M, Quince, J.Jill, Madewell and J.Crew instead of longing for logos. For inspiration, take a look at the sophisticated Quince Women Mongolian Cashmere Boatneck Sweater in Oatmeal, Truffle Brown, Heather Charcoal and Black ($80, quince.com), the head-turning H&M Women Tie-Belt Shirtdress in Cream/Zebra Print ($30, hm.com), the elegant Madewell Women Double-Faced Cropped Chore Jacket in Light Heather Gray ($248, madewell.com), and the refined Mango Women Suede Shoulder Bag With Stitching in Brown ($180, shop.mango.com).

a model wearing a black leather knee length skirt, a model wearing cropped beige velvet trousers and a pair of black kitten heel pumps with pointed toes

(From left) Kenneth Cole Women’s Faux Leather Wrap Skirt in Black; Eileen Fisher Corduroy High-Rise Ankle Jeans in Biscuit; LifeStride Women’s Madelyn Mary Jane Kitten Heels in Black Sheer.

AARP (Macy’s; Bloomingdale’s; Kohl’s, 2)

8. The mistake: classic clothes get boring

Many women over 50 prefer their clothes on the traditional side. They tend to buy and wear the same kinds of clothes year after year and often put outfits together in the same way. As a steady fashion diet, their closet and outfits can feel dull, stuffy and boring. This is when women say to me, “I have nothing to wear” and “How can I look new when I’m not into trendy clothes?” It’s easier than you think.

The solution: One way out of this predicament is to start mixing your wardrobe pieces. Pair basics with fancy, sporty with tailored, day with night. This is what fashion stylists do, even with conservative clothes. It expands your wardrobe and allows you to be more creative. Afraid you’ll look messy or get it wrong? Here are three tips.

First, know that if you stick to a neutral or one-color scheme, everything “goes” with everything. Next, change how you wear your clothes and give them a modern, lived-in look. Roll your sleeves and unbutton button-downs to a V; untuck or half-tuck tops. Lastly, add new classics, like Mary Jane kitten heels and contemporary versions of classics — ankle pants instead of full-length, or a pleated or wrap skirt in leather — this time around.

Good examples include the LifeStride Women’s Madelyn Mary Jane Kitten Heels in Black or Black Sheer ($80, kohls.com), Eileen Fisher Corduroy High-Rise Ankle Jeans in Biscuit ($139, bloomingdales.com), and the Kenneth Cole Women’s Faux Leather Wrap Skirt in Black ($119, macys.com).

a model wearing a black knee length belted dress, a model wearing a beige rib knit ensemble with an off shoulder top and a model wearing a light green velvet asymmetrical top with black trousers

(From left) Lane Bryant Ponte Twill Tie-Waist Long-Sleeve Dress in Black; Universal Thread Women’s Off the Shoulder Top in Oatmeal; Banana Republic Factory Women Velvet Off-Shoulder Top in Douglas Fir

AARP (Lane Bryant, Target, Banana Republic Factory)

9. The mistake: thinking cleavage and short skirts are sexy

Some women say, “My legs are still good enough for minis!” and “My bust is great! Who says no showing cleavage?” That level of body pride is terrific, and how much breast or leg you choose to reveal is really your own business. However, here’s my advice for those women over 50 who — like Sylvie in Emily in Paris — wear necklines down to there and dresses up to here without a care. It’s fun to see celebs over 50 take fashion risks on film and the red carpet, but c’mon, set some boundaries.

The solution: Designate one dare-to-bare show-off spot at a time, making it relevant to where you are and what you’re doing. If you’re interested in flattery, consider issues like sun damage, varicose veins and crepey skin before you leap.

For most women over 50, the shoulders have become a universal show-off spot that works well in situations where you want to look sensual or just sexy. That’s because shoulders — which frame your neck, collarbones and upper chest — will always have an appealingly firm, smooth, sculptural look regardless of our weight, size or shape. You can’t lose with off-the-shoulder tops such as the Ann Taylor Ribbed Off-The-Shoulder Sweater in Aubergine or Winter White ($69, anntaylor.com) and the Universal Thread Women’s Off the Shoulder Top in Black or Oatmeal ($30, target.com), or one-shoulder variations like the Line & Dot Favorite Geometric Neck Sweater in Black ($79, bloomingdales.com) and the Banana Republic Factory Women Velvet Off-Shoulder Top in Black, Douglas Fir or Dusty Calliandria ($41, bananarepublicfactory.gapfactory.com).

If you’d rather highlight your legs, try a knee-length or just-covering-the-knee skirt or dress with some swish at the hem, like the Kasper Pleated Hem Pencil Skirt in Vanilla Ice ($79, nordstrom.com), or the fit-and-flare Lane Bryant Ponte Twill Tie-Waist Long-Sleeve Dress in Black ($66, lanebryant.com) — and add your favorite kitten heels.

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Lois Joy Johnson is a beauty and style editor who focuses on women 50 and older. She was the beauty and style editor at Ladies’ Home Journal and a founding editor of More magazine. She has written three books: The Makeup Wakeup, The Wardrobe Wakeup and The Woman's Wakeup.