6 Tips for Wearing Skirts Over 65, According to Style Experts

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Skirts are a style necessity, no matter your age.

Skirts are a staple in any wardrobe; they can be dressed up or down, worn with or without tights, and come in a range of lengths and styles. But as we get older, it can be harder to find the right fit and recognize what works for our shape, with skirts proving especially tricky. Thankfully, fashion experts assure you that there are a few key tips for wearing skirts over the age of 65.

“Skirts are a great way to add a touch of femininity … They can be flirty and fun or sophisticated and stylish,” Ai Hiura, fashion expert and chief marketing officer at Faverie, tells Best Life. As it turns out, a little bit of experimentation might be necessary. Read on to find out what Hiura and her fellow style experts recommend keeping in mind when styling a skirt later in life.

1. Consider your body type.

Different styles work best on certain body types, so you’ll want to consider your size and shape when it comes to skirts.

“If you’re petite, maxi skirts may swamp you, whereas a midi length might fit you better,” Becca Brown, brand marketing manager at clothing retailer Dancing Leopard, explains. “Equally, if you’re tall, a maxi length might fit you better than a midi.”

Emma Strzelecki, personal stylist at Emma Louise Styling, recommends going for “a long flowy skirt that will balance out your proportions” if you’re top-heavy. And if you’re pear-shaped, Hiura suggests trying an A-line or pencil skirt. No matter what skirt you go with, be sure to pick one that fits correctly.

“Ill-fitting skirts can be very unflattering, regardless of your age,” Kate Smith, co-founder and director of marketing at ZippiLeather, tells Best Life. “Make sure the skirt is not too tight or too loose and that it doesn’t gap at the waist.”

2. Try tucking your shirt in.

According to Strzelecki, before you invest in a new skirt, you should also think about how you’re going to style it. This includes jewelry and other accessories, as well as what you’ll wear as a top.

“You could pair it with a t-shirt, buttoned cardigan, or blouse—depending on how casual or smart you’re going,” Strzelecki says, adding that tucking your shirt in will probably be more flattering for your proportions.

“Always tuck your top in—the right skirt will skim over your tummy anyway, if that’s an area you’re worried about,” she adds. “If you leave it untucked, make sure the top ends at your waist otherwise you’re going to cut your body in half—a style no-no.”

3. Choose the right shoes.

The right skirt will require you to consider your entire look, from top to bottom. This, of course, includes your shoes.

“The wrong shoes can ruin even the best-looking outfit,” Smith says. “Choose shoes that are comfortable and that go well with the skirt. Avoid excessively high heels if you’re over 65, as they can be difficult to walk in and may cause you to trip.”

You can opt for a trendy sneaker or sandal, but Jon Callahan, founder of Thread Curve, recommends pairing your skirt with at least a small heel.

“Combine with patent leather pumps for the evening or black tights and booties,” he says. “Wear wedge shoes, high-heeled pumps, or boots instead of flat shoes.”

4. Try a slip skirt.

If you’re still unsure of the kind of skirt that will work best for you, Brown says that you can’t go wrong with a slip skirt. These skirts are particularly trendy right now, meaning you shouldn’t have too much trouble finding one at your favorite store.

“Whatever your height, slip skirts are a fail-safe option,” she explains. “They’re comfortable in shape, they suit every figure, and they’re really stylish right now.”

As a convenient bonus, they’re versatile and can be worn for a variety of occasions. “Add a knitted sweater and a pair of boots in the day, or wear with a nice top and heels for evening events,” Brown recommends.

5. Colors and patterns are your friends.

You may think that as you get older, you need to stick to “slimming” shades like navy and black. However, this couldn’t be further from the truth, fashion experts say.

Hiura notes that there are “no hard and fast rules” for colors and patterns of skirts. As with different styles, you’ll have to go through some trial and error.

“Just experiment until you find something you love!” she says, suggesting floral prints or bold solid colors, if you’re more comfortable. “Don’t be afraid to try out unique patterns like polka dots or stripes. The key is just having fun with it and not taking yourself too seriously.”

6. Rock that confidence.

If all of your skirts ended up in a donation bin, consider trying one on the next time you do a wardrobe refresh. The right clothes can make you feel good, helping you appear genuinely comfortable in your own skin.

“The most important thing to remember when wearing a skirt over the age of 65 is to be confident in yourself,” Brown says. “If you don’t feel good about what you’re wearing, it will show and you won’t look your best. Wear something that makes you feel fabulous and enjoy showing off your legs!”

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