The Worst Style Mistakes Women Over 50 Are Making Right Now

Mistake #3: Going overboard on oversized clothes

We can’t get enough of billowy A-line skirts, breezy wide-leg pants and gigantic oversized tops, especially for spring and summer. But there’s a difference between spacious clothes and a fit that looks sloppy or visually piles on pounds. You’re going off the fashion track when your fit veers into tent territory and your look lacks even a hint of body definition. 

The solution:

Put that extra volume to work where your curves, bulges and psyche benefit from ease and stylish camouflage. One way is to designate your top or bottom for the “big” piece and balance it with a slimmer or more fitted item. 

For example, you might wear an oversized shirt like the Sonoma Goods For Life Oversized Boyfriend Shirt in Bright Pink Stripe or White Green Stripe ($25, kohls.com) with slim straight pants or jeans, or a pair of wide-leg pants like the Gap Women Linen-Blend Easy Wide-Leg Pants in Tomato Sauce Red ($80, gap.com) with a torso-skimming tee. Fit-and-flare dresses like the Banana Republic Factory Gathered Elastic-Waist Midi Dress in Cape Blue ($70, bananarepublicfactory.gapfactory.com) are another way to wear generously cut clothes, since the volume is controlled by shaping at the waist.

That said, the oversized shirt rules the “big” category and has become a go-to wardrobe staple. But all that fabric can be tricky. For maximum flattery, unbutton the neck to a V, and roll the sleeves up to reveal your wrists and forearms. Here’s a question I’m often asked: “What’s the difference between an intentionally oversized button-down and one that’s regular fit in a size up from your standard size?” The oversized shirt will be wider and looser but all in proportion, while the upsized regular fit will be moderately looser at the torso and may have unwanted extra length at the bottom, sleeves and shoulder line. Shirts that say “oversized,” “boyfriend” or “relaxed” are a better choice.

Gloria Vanderbilt Women’s Knitology Amanda Pull-On Straight Jeans in Metzen W Whiskers

Kohl’s

Mistake # 4: Thinking trendy new jeans solve everything

Most women over 50 know their way around jeans by now. That’s why they’re choosing higher rises and stretch denim to tuck in bellies and muffin tops, and wearing flares and wide-legs for a fashion boost. However, when the fit of your jeans is off, all that know-how goes down the drain. 

Many women tell me that high waistbands feel uncomfortable and leave their bust and waist competing for midriff space. They complain about flares and wide-leg jeans feeling too trendy and secretly miss the legging-like hug of skinnies. The range of body proportions and jean styles is mind-boggling, but two shortcuts to flattery can get your fit chops back on track.

The solution:

This is a two-step trick. First, know that your best rise may not be high after all. Mid-rises often provide the extra inch or two that makes all the difference for a large bust or a short torso and expand the variety of tops you can wear. Don’t be trapped by rise labels — here’s why.

Mid-rises are around 8 to 9.5 inches, and high rises are 9 or 9.5 to 11.5. Oftentimes a high mid-rise can be better than a low high-rise. Aim for jeans that sit around an inch (give or take a bit) above your belly button. This elongates your torso while providing enough coverage for a belly bulge. And while straight-leg jeans may not sound as sexy as flares or as much fun as barrels or wide legs, they offer a slim, trim line without the squeeze (and sometimes sleaze) of skinnies. 

Check out no-fail straight styles like the Gloria Vanderbilt Women’s Knitology Amanda Pull-On Straight Jeans in Metzen W Whiskers ($25, kohls.com) which have a flat front that defies bellies, J. Crew Factory Women Essential Straight Jean in All-Day Stretch in Black ($60, factory.jcrew.com) and Loft Mid Rise Relaxed Straight Jeans in Dark Wash ($45, loft.com).

(From left) LC Lauren Conrad Women’s Floral Crepe Godet Midi Skirt in Green Virginia Vines; Future Collective Brown Women’s High Rise Full Lining Midi Pull-On Skirt in Brown; Simply Vera Vera Wang Women’s Shirred Midi Skirt

AARP (Kohl’s, 2; Target)

Mistake #5: Counting on midi skirts to flatter your legs

Many women over 50 have become midi fans. Lured by not having to worry about a rise or the fit at the hips, thighs or derriere — and also by being able to sit however they want — they really love the ability to fashionably ignore leg veins and discolorations. 

The sticking point here? The hemline. The term “midi” is varied and flexible. It ranges from skirts and dresses with a hemline just below the knee to ones that end a few inches above the ankles. Since we all have varying leg proportions, it’s rare that a midi dress or skirt is a one-hemline-suits-all situation. Your leg shape can determine whether a midi’s length is divine or a disaster on you.

The solution:

Some midis are mislabeled maxis, and vice versa. Whatever they’re called, the worst fit for a hemline is right at the widest part of your calf. It flatters no one, makes full calves appear even wider and creates the illusion that your legs underneath that skirt are chunky. Every inch counts. Choose a length above your calf at the narrow part just before the swell begins or below the calf. If need be, take your midi dresses and skirts to a tailor to alter the hemline. 

For inspiration, take a look at the Future Collective Women’s High Rise Full Lining Midi Pull-On Skirt in Brown ($36, target.com), J.Crew Factory Women Eyelet Midi Skirt in Bright Rose ($45, factory.jcrew.com) and LC Lauren Conrad Women’s Floral Crepe Godet Midi Skirt in Green Virginia Vines ($38, kohls.com). Avoid skirts with complicated hemlines like scallops or pleats if you’re counting on a tailor’s assistance.

(From left) Lane Bryant Linen 3/3-Sleeve Jacket in White; A New Day Women’s Lady Jacket in Black

AARP (Lane Bryant, Target)

Mistake #6: Pairing office blazers with casual clothes

Many women give old workplace blazers and pantsuit jackets a second life by wearing them to dress up jeans and tees or even flowy dresses. Here’s the problem. While your other clothes continued to get frequent fit updates, the jackets didn’t. Unlike a vintage bag, which never gets old, office blazers, even those with a fancy designer label, can look dated, fussy and stiff, or totally out of touch with a modern fashion aesthetic. Surprised? The oldies often have too-wide sleeves, armholes cut too low and a boxy shape. Many have obvious shoulder pads that are large, extended or droopy.

The solution:

Removing the aging shoulder pads and raising the shoulder line from the neck to the shoulder joint will give those jackets a smoother fit. This latter step is essential, since taking out the pads results in excess fabric that can cause the front of the jacket to buckle and crease when you sit. Ask your tailor to slim down the sleeves as well. This will raise the armhole and give your arms and bust a firmer silhouette. Love your boxy, shapeless blazer? Take in the sides for a subtle nipped waist that’s more flattering and makes legs appear longer. 

The other option is to buy a new blazer or a cropped “lady jacket” with a more contemporary silhouette that blends easily with your current clothing. Good choices include the Lane Bryant Linen 3/4-Sleeve Jacket in White ($120, lanebryant.com), A New Day Women’s Lady Jacket in Off-White ($48, target.com) and the Banana Republic Women Everywhere Ponte Blazer in Black ($200, bananarepublic.gap.com)