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How To Dress Like A (Fabulously Stylish) Grownup

"I’m 41, and I’ve long suffered from 'Closet Full of Clothes But Nothing To Wear' Syndrome."

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A graphic of a woman surrounded by various pieces of clothing.
Alice Rutherford
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Hi, my name is Leslie, I’m 41, and I’ve long suffered from “Closet Full of Clothes But Nothing To Wear” Syndrome.

*Hi, Leslie*

For my 40th birthday, my husband sent me on a surprise girls’ trip to NYC. While there, my besties shepherded me to a dozen or so stores and helped me build a new wardrobe, encouraging me to try on things I normally wouldn’t (black vegan-leather leggings at Aritzia — got ’em! Fit-and-flare jeans from Anthropologie — check!). Back home, my most stylish friend, Amanda, came over and helped me sort through my old stuff, Marie Kondo-ing pilled sweaters from the early aughts and some business-casual attire I’d been holding onto, despite the fact that my office hasn’t been an actual office since 2007.

Wearing those new clothes — pieces that made me feel pulled together, stylish and cute — turned out to be far more enjoyable than I ever realized. It was so fun to put new earrings in every morning and to slip on fitted tanks, white jeggings and maxi dresses — after years of alternating between black yoga pants and black yoga pants. Dressing like a grownup was delightful!

With that in mind, here are a few expert tidbits to consider should you, too, decide to redo your 'drobe:

First, prune your existing wardrobe.
Style blogger Jane Younger (@dirtymartinisandskinnyjeans) recommends asking yourself if the items in your wardrobe make you feel confident and happy when you wear them, if they fit, and if they successfully represent your current style. Also: Have you even worn it in the last year? “If the answer to any of these is ‘No,’ ” says the 60-something fashionista, “it’s time to sell, donate or trash it.”

Want to break out of the athleisure rut?
Kelly Hover, personal shopper and owner of BeYOUtiful Image Consulting in Grand Rapids, Michigan, points out that “it takes you the same amount of time to put on yoga pants and a T-shirt as it does to put on a pair of jeans and cute top.” She recommends a simple three-step process: First, grab a bottom and a top — it could be jeans and a tank, dress pants and a long-sleeved button-up shirt, or anything in between. “Next, add one layering piece for visual interest,” Hover says. “It could be a blazer, jacket, cute hoodie, scarf, kimono, cardigan — anything!” And then, add in some jewelry. “It’s the last thing you put on, but one of the first things people notice.”

Accessorize, accessorize, accessorize.
With the right add-ons, the same core outfit can pull triple duty at the park, running errands or meeting a girlfriend for dinner, says Bridgette Raes, a personal stylist and the author of Style Rx: Dressing the Body You Have to Create the Body You Want. Let’s say you start with a green T-shirt dress. “You can pair it with coral studs, a metallic diaper bag and pop it with a pair of orange flip-flops for the day, or swap in wedges, dangly fuchsia earrings and a cute handbag for night.”

Be true to yourself.
Don’t be afraid to try out the trends. “You can still dress youthfully, no matter what your age is,” says celebrity stylist Elizabeth Stewart, 54, whose clients include Cate Blanchett, Viola Davis and Julia Roberts. She gave the example of popular floral patterns. “My daughter is a college freshman and we both have the same floral tank. I add a black jacket over mine so just a hint of floral peeks out; she wears hers with short shorts.”

Currently partnering with Walmart, Stewart says trying out trends feels fun and refreshing and can even boost your confidence levels, but adds that the most important thing is “that you feel comfortable and happy when you put your clothes on.”