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The 10 Biggest Outfit Mistakes for Women Over 50

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


illustration of red x through four different outfits
AARP (Getty Images, 6)

Who doesn’t struggle to pull together a flattering and fashionable outfit? As a fashion editor, stylist and personal shopper for women over 50, I see every mix, match and style mistake in the book. Despite what you may think, fashion faux pas are not really all about having the wrong clothes. It’s more about how you choose and put together the pieces in your closet. Here are the 10 most common outfit mistakes and how to fix them.

two women in black dresses
(Left to right) Madewell Tie-Waist Straight-Leg Jumpsuit in True Black; Quince Mongolian Cashmere Wide-Rib Midi Dress in Black
AARP (Madewell, Quince)

1. The mistake: Being underdressed or overdressed.

Situation 1: You’re in joggers, a mock neck and sneakers, and everyone else is in dresses or fancy tops, slingback heels and full makeup. Situation 2: You’re in a flow-y dress and velvet Mary Janes, and everyone else is in jeans and sweaters. Both feel like a bad dream, but scenarios like these happen to all of us. Dressing too casually or too glam for a situation is one of the most common outfit mistakes women over 50 make.

The solution: Take the middle road but aim on the high side.When you’re unsure of the dress code being a little overdressed earns compliments; being underdressed gets the side-eye. My motto is it’s better to stand out in a crowd for your style than for your lack of it. An elevated head-to-toe outfit in black never fails. This can be anything from black pull-on pants and a black cashmere boatneck sweater to a jumpsuit or a black sweater dress. Not too dressy, not too casual. The last trick is to add one standout accessory — great shoes or a dramatic bracelet that lift a solid basic to special. Try these for starters: The Quince Mongolian Cashmere Wide-Rib Midi Dress in Black ($150, quince.com), the Madewell Tie-Waist Straight-Leg Jumpsuit in True Black ($180, madewell.com) and the Ross-Simons Sterling Silver Wide Polished Cuff Bracelet ($269, ross-simons.com).

2. The mistake: Wearing out-of-date clothes.

Some women recycle their old clothes and say, “It’s in again! So glad I saved it!” They add items like an 80s power blazer with huge shoulder pads, a real leather jacket with fringe and studs, platform pumps and low-rise whiskered bootcut jeans. However, there’s a difference between a stylish comeback and items that date your outfit and you. Fashion trends do circle back every 20 years or so, but they’re never exactly the same — and neither are our bodies, which means some of those pieces you covet are not doing you any favors. For example, new blazers are relaxed and feature small shoulder pads for structure not attention; leather jackets are now mostly faux leather and have a streamlined look; platforms are on loafers and sneakers, not heels; and bootcut jeans are high waisted, in even washes and comfy stretch denim.

The solution: Love the vintage, but get choosy about which items are worth a wear. Select one piece to give a contemporary outfit a dash of personality. Those that are most successful now: trendy-again bag shapes like 90s baguettes, fanny packs (wear them as crossbody slings this time around) and chain-strap shoulder bags (wear them as a crossbody too); statement cuffs, pendants and large earrings; kitten-heel shoes and colorful traditional cardigans to spark ho-hum outfits (try wearing them as tee substitutes), faux fur in jackets and coats, and of course, anything in an animal print. Leopard never ages.

a pink sweater and a neutral stripped sweater
(Left to right) Boden Women Catriona Cotton Crew Sweater in Carmine Rose Pink; Charter Club Women’s Striped 100% Cashmere Turtleneck Sweater in Pearl Taupe Heather Combo
AARP (Boden, Macy’s)

3. The mistake: Trying to mix colors and prints like a YouTube influencer.

Pushing the boundaries of what you wear can be fun, but misguided mixes are everywhere. Wearing two unexpected colors and combining prints really does take a little restraint and know-how. There are two foolproof ways to avoid a faux pas. One is to combine prints with a common color theme; the other trick is to combine solid colors within the same cool or warm category.

The solution: Arrange your closet by color to make both strategies a snap. Most women have more same-color pieces than they think. Make sure you include prints and textures from every season, day and night. You might pair a striped sweater in black, brown and gray with a floral skirt in the same colors like the Charter Club Women’s Striped 100% Cashmere Turtleneck Sweater in Pearl Taupe Heather Combo ($83, macys.com) and Nation LTD Belinda Print Button Midi Skirt in Night Floral ($180, nordstrom.com), or wear a leopard blouse with a brown and tan plaid blazer.  Combining two solid colors in a pleasing way is even easier. Just choose two warm tones — like hot pink with red, as in the Boden Women Catriona Cotton Crew Sweater in Carmine Rose Pink ($60, bodenusa.com) shown with red pants. Leave more extreme mixes of complementary colors — like purple and yellow, blue and orange — to the runways.

black fitted jeans and a tann. flowing skirt
(Left to right) J.Jill Smoothing Ponte Leggings in Black; Vineyard Vines Metallic Pleated Midi Skirt
AARP (J. Jill, J. Crew)

4. The mistake: Overdoing the skintight look.

Many mature women still love the form-fitting effect of leggings, skinny jeans and snug tops. It’s the payoff for losing a few pounds, a consistent exercise regimen or a self-love reset. But the pleasing hug of these pieces can turn sour when both top and body are clingy.

The solution: You have two choices. Balance a tight bottom with a looser top or modify cling on top with a looser bottom. Grab any tunic top, spacious button-down or slouchy sweater and slip on your leggings or skinnies. Or keep the bodysuit or fitted top and swap skinny bottoms for an A-line midi skirt or wide-leg pant. No need to go to extremes. Even modified volume, as in relaxed tops and pants or straight-leg jeans, offers enough room for contrast if extra volume isn’t on your love-to-wear list. Check out the J.Jill Smoothing Ponte Leggings in Black, ($79, jjill.com) shown here with a white tunic and long vest, the Cupshe Women’s Striped Drop-Shoulder Sweater in Colorblock ($37, target.com) over skinny jeans, and the Vineyard Vines Metallic Pleated Midi Skirt ($120, nordstrom.com) worn with a snug striped top.

two women in black pants and a black belt
(Left to right) Banana Republic Factory Cable Turtleneck Sweater in Black; The Colette High-Rise Cropped Wide-Leg Jeans by Maeve: Sparkle Edition in Rinse Wash-Plus; Zara Women Rectangular Buckle Thin Belt in Black or Burgundy
AARP (Banana Republic, Anthropologie, Zara)

5. The mistake: Going all in on the voluminous trend.

Some women have fallen in love with the aah factor of generously cut clothes and their ability to camouflage extra pounds. It explains why they’re snapping up oversized button-downs, boyfriend blazers, roomy drop-shoulder sweaters, wider pants and long full skirts. So, here’s the problem. Sometimes these outfits look great on tall, thin models — but in real life make you look bigger, boxier and shapeless. One of the secrets to a more becoming look is to reveal your neck, forearms or ankles. Head for a V-neck, boatneck or ballet scoop neckline instead of crewnecks, three-quarter or rolled sleeves; ankle-cropped pants instead of full-length ones; and midis instead of maxis. Exposing these three spots can prevent you from drowning in excess fabric.

The solution: Another quick tip is to put together roomy pieces in the same color to create “flow” and a vertical line. You can also suggest a waist by doing a half tuck of the top or loosely belting airy tunics, cardigans and dresses. Take a look at The Colette High-Rise Cropped Wide-Leg Jeans by Maeve: Sparkle Edition in Rinse Wash-Plus ($138, anthropologie.com), shown with a loose shirt and half-tuck. You don’t need a narrow waist to do the body “cinch,” just a slight indent with a narrow belt like the Zara Women Rectangular Buckle Thin Belt in Black or Burgundy ($25, zara.com/us) is enough to add just a hint of shape.

6. The mistake: Wearing uncomfortable clothes and accessories.

Looking fashionable isn’t worth wearing outfits that are disruptive. Trust me, if what you’re wearing doesn’t feel good, it won’t look good and will show up in your body language and expression. Offenders include: fabulous heels that are too high; pointed-toe flats that pinch; itchy sweaters; annoying skirts with tight waistbands; asymmetric hemlines or high slits that make sitting a challenge; pants and jeans that are too short in the rise and reveal muffin tops; and heavy earrings that hurt your lobes. Donate them ASAP.

The solution: Take a tough-love approach and delete anything in your closet that makes you tug, fidget and complain. Substitute flats, wear only skin-friendly fabrics, go up in pant rise, choose skirts with elastic waists, even wide hemlines and no slits, and opt for lightweight earrings or switch to necklaces and bracelets for bling. The payoff is a smile.

red shoes
Bibi Lou Suzy Pumps in Red at Anthropologie
AARP (Anthropologie, 3)

7. The mistake: Taking the classic match-y match-y route.

Some women like to look “coordinated.” They insist on shoes, belts and bags that “twin” in color and tone to their outfit. They’re fairly strict about wearing tailored pieces with tailored accessories, casual or sporty ones with their mates in shoes and bags. There’s nothing wrong with this tactic — in fact, going for a head-to-toe monochromatic effect can look incredibly posh. The downside? As a daily diet, your outfits can begin to feel dull and stuffy.

The solution: Get more creative and stop playing it safe. Mix categories — day and night, tailored and sporty, classic and trendy — in the same outfit. Use white tops and jackets to brighten dark neutrals and your face, and add pops of unexpected blush and lipstick colors like pink and red in clothing and accessories to wakeup-tired looks and outfits. You might try the Uniqlo Women Knitted Short Jacket in 00 White ($50, uniqlo.com/us), the Banana Republic Women’s Cashmere Rugby Sweater Polo in Wild Orchid Pink ($150, bananarepublic.gap.com) and the Bibi Lou Suzy Pumps in Red ($130, anthropologie.com) to kick off a change.

black and tan wide leg pants
Gap Women High Rise Stride Wide-Leg Ankle Khakis in Black and Classic Khaki Tan
AARP (Gap, 4)

8. The mistake: Not tweaking the fit for your body.

So you snapped up a jumpsuit, a fast-fashion dupe of a trendy skirt and top, or finally bought the pants you’ve been eyeing. Now what? When clients show me their “great buys,” nine times out of 10, the outfits are a bad fit. They’re too big, too long or too short, too baggy or shapeless. The seats of pants sag, skirts stop at the widest part of the calves, pants dribble over shoes, jacket sleeves cover the hands, and button-downs are so big they’re more like caftans than shirts. Visually this adds up to a sloppy look, like you’re wearing someone else’s clothes. Remember: You can be 5-foot-1 and wear the same size 14 as a woman who is 5-foot-7. This includes “ankle pants” and “midi” hemlines that fall to full length and maxi length on women who are under 5-foot-2. Even petite sizing can use an adjustment.

The solution: Haul all new pieces (and old clothes you wear often) to the tailor. Just getting skirts, pants and jeans, and jacket sleeves hemmed to the right length for your proportions makes a huge difference. And please do a DIY snip of the tacking stitches that keep clothes purchased online in shape when they are shipped to consumers. Pockets are often basted closed; skirt and jacket vents are stitched, too. They’re meant to be removed the minute you decide to keep them. You’d be shocked how many women neglect to do this!

two pairs of flats and a purse
(Left to right) Mango Women Shopper Bag with Padlock; Everlane’s The Day Glove Shoe in Bordeaux Suede; H&M Women Ballet Flats in Beige/Black
AARP (Mango, Everlane, H&M)

9. The mistake: Overdoing branding and logos.

Being a brand snob has become a national habit. There’s nothing terrible about wearing well-made, stylish clothes and accessories with a visible designer name or logo until it becomes the focus of your entire outfit. We’ve all seen women wearing a bag covered in famous initials and shoes, belts and bracelets boldly ID’d with a signature buckle or closure, and even sports and athleisure apparel that shouts a brand name. Even look-alike brands that mimic the patterns and design of well-known labels get in on the fun. The point of a great outfit is making you look and feel good, not to be a walking ad or a boast about your paycheck.

The solution: Limit an outfit to one or two branded items at a time. Consciously wearing a special designer item, whether it’s an Louis Vuitton tote or a pair of Tory Burch ballet flats, is fine, but resist piling on logo on logo. Instead try adding some super-stylish looks like Everlane’s The Day Glove in Bordeaux Suede (on sale now for $69, everlane.com), the H&M Women Ballet Flats in Beige/Black ($25, hm.com/en_us) or the Mango Women Shopper Bag with Padlock ($56, mango.com/us) to your accessory lineup.

three women in midi skirtts
(Left to right) Loft Cozy Off the Shoulder Midi Sweater Dress in Silver Oat; Eloquii Colorblock Column Skirt in Black + White
AARP (Loft, Eloquii, Loft)

10. The mistake: Displaying too much skin.

Some women over 50 have the magical ability to ignore a sun-damaged chest and leg discolorations. Others pay no attention to flabby thighs and chubby or dangling upper arms. Both wear whatever they want, whenever. Hooray for them! This attitude is admirable, especially in summer, on a tropical beach vacation, for sports and gym workouts. But how about at work and social events? The truth is there’s a fine line between looking sexy and comfortable in your own skin and looking tacky. Aside from the above situations, wearing an outfit that reveals way too much skin — a dress with a plunging V neckline (front or back) at work or a spaghetti strap slip dress and a too-high slit skirt to a party — can look a little desperate. Unless you’re a celebrity, designate one show-off spot to bare and make it relevant to where you are and what you’re doing.

The solution: Great shoulders are one spot that every woman can display, as in the Loft Cozy Off the Shoulder Midi Sweater Dress in Silver Oat ($40, loft.com). V necklines that “land” above cleavage crack are more flattering than those that do a deep dive, and legs can look elegantly fabulous in a knee-ish skirt like the edgy NYDJ Faux Leather A Line Skirt in Black ($67, bloomingdales.com). On the other hand, even being fully covered can be provocative and sophisticated if you opt for supple fabrics like silk, satin, cashmere and knits like the Eloquii Colorblock Column Skirt in Black + White (on sale now for $20, eloquii.com) and the Jessica London Women’s Plus Size Wide-Leg Knit Jumpsuit in Chocolate ($46, target.com) that slide over and around curves.  

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