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5 Must-Have Clothes to Transition to Fall as You Get Older

If you own them, you'll always have something to wear, stylists say.

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Transitioning your clothing from summer to fall can be tough. First, there's the temperature problem: The mornings are cool, and the afternoons are often sweltering. Then there's the problem of which season to dress for: Raise your hand if you've ever worn a floaty linen dress at the beginning of September just to walk into a room where everyone's paired a corduroy skirt with their coziest fall knit.

However, if you have the right staples, dressing for those transitory weeks between seasons gets easier. Here, we polled personal stylists to find the key pieces every woman who's getting older should have in her wardrobe to tackle the days between summer and fall. From strategic sweaters to the key jackets you'll wear on repeat, stock up on these items for great style from summer to fall and beyond.

RELATED: 6 Tips for Revamping Your Wardrobe as You Get Older, Stylists Say.

Leather Leggings

woman in leather leggings
Oleg Elkov / iStock

Early fall is all about activities: pumpkin picking, cider tastings, and easy hikes through gorgeous leaves. One thing you'll want to prioritize through all of that is comfort—and that's where leather leggings come in.

"Pair leather leggings with a turtleneck, knit cape, statement belt, and rugged boots for a weekday look, or an extra long T-shirt, faux fur vest, and fashion sneaker for a weekend warrior vibe," says certified image stylist Elizabeth Kosich, founder of Elizabeth Kosich Styling. "Both have layers that can be piled on and peeled off depending on the temperature."

Bonus points: As the mercury dips even lower in the winter, this will still be a go-to piece. How's that for an almost year-round staple?

RELATED: 5 Tips for Wearing Turtlenecks If You're Over 60, According to Stylists.

Cashmere T-Shirt

cashmere sweater
goldnetz / Shutterstock

As it gets closer to Labor Day, you can swap out your everyday T-shirt for a cashmere one.

"It is a great option that is more formal than a standard cotton T-shirt but is still easy and convenient to throw on," says Andie Sobrato, a personal stylist and image consultant. "I find they really pair with everything so that they can be worn with jeans for a more casual look, trousers for a more corporate look, and even a skirt if you want to be dressed up."

Your arms are exposed, but the knit keeps you snug. Sobrato loves this version from Quince.

Another knit option is a short sleeve cardigan or crochet top. "They can be paired with a sleek trouser for work or even a dark flared jean for a more casual evening," says Sobrato.

RELATED: 7 Ways to Dress Trendy Over 60, Stylists Say.

Tunic Dress

older woman in maxi dress
Roman Samborskyi / Shutterstock

We're all in search of those elusive summer-to-fall dresses. Kosich's recommendation is a tunic. In the summer, wear them with just a hint of jewelry and a sandal. Then, you can add opaque tights and a ballet flat.

"Add a moto jacket for extra warmth and then, as temps drop even more, layer a skinny turtleneck under the tunic," Kosich adds. "It's a whole new look for your fave summertime dress, only winterized."

This technique works with other types of midi-length dresses with sleeves, too. Sobrato's pick is one in a ribbed jersey material with buttons down the front.

"What's great about a dress like this is that you can dress it up with heels, dress it down with sneakers or even pair it with boots in the fall," she says. During transitory seasons, it's all about versatility.

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Linen Blazer

A cheerful senior couple is outside in the city walking on the street, socializing and drinking coffee.

Toward the end of summer, you'll also want to start thinking about light layers. "A linen blazer is a lightweight layer that can be worn with jeans, wide-leg trousers or even a skirt," says Sobrato.

Wear it with a culotte pant and block heel and get ready to hit the town. Or, toss it on over a shift dress for the office. It's the perfect piece to leave at your desk should the AC get too chilly.

Moto Jacket

older woman classic leather jacket

The final piece in your transitory capsule should be a moto jacket.

"Add layers under it, or over it, and watch how it delivers on both form and function without fail," says Kosich. "Pair with wide-leg trousers, a Breton tee and platform sneakers for a chic, understated look—for more warmth, add either a skinny turtleneck under the Breton tee or a cropped pea coat over the moto jacket."

If you choose this piece wisely, it'll serve you for decades. Leather jackets never go out of style.

Juliana LaBianca
Juliana is an experienced features editor and writer. Read more
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