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6 Secrets of Stylish Women

Insider tips on looking effortlessly cool 


spinner image from left to right fashionable actresses over fifty jane fonda angela bassett oprah and jennifer anniston
Photo by Dimitrios Kambouris/Getty Images for Tribeca Festival / Photo by Emma McIntyre/Getty Images / Photo by Lorenzo Palizzolo/Getty Images / Photo by Hollywood To You/Star Max/GC Images

Some women always look pulled-together and fashionable (even at the grocery store or gas station) and it drives the rest of us crazy. What do they know that we don’t? As a fashion editor, stylist and personal shopper specializing in women 50-plus, I’ve dressed thousands of women for photo shoots and real life, and I have learned that style boils down to just a handful of tips. Here are the wardrobe-boosters the fashionable crowd have been keeping to themselves. Pass it on.

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spinner image Madewell The Perfect Vintage Wide-Leg Jean in Heathcote Wash; Zara Women Faux Suede Overshirt in Pink; Gap Satin Shirt in Stone Beige
MADEWELL / ZARA / THE GAP, INC.

1. Wear modified versions of trends

The truly stylish avoid extremes. Instead, they look for newish items that will not only rejuvenate their wardrobes but will stick around for more than one season. A hot pink “Barbiecore 2023” blazer may grab your attention, but a muted pink shacket like the Zara Women Faux Suede Overshirt in Pink ($48, zara.com/us) is more wearable and versatile. A satin slip dress? Too “junior,” but a satin blouse like the Gap Satin Shirt in Stone Beige or Black ($70, gap.com) looks sophisticated without trying too hard. Wide-leg cargo jeans with patch pockets? No way. But streamlined jeans with moderate proportions like Madewell’s The Perfect Vintage Wide-Leg Jean in Heathcote Wash ($128, madewell.com) provides enough of an update without going over the top in volume. In other words, get inspired by fashion but don’t take it too seriously.

spinner image Quince Super Luxe Baby Cashmere Turtleneck Sweater in Charcoal; L.L. Bean Women’s The Essential Sweater, Turtleneck in Medium Charcoal Heather; Abercrombie & Fitch Tuckable Easy Turtleneck Sweater in Taupe
QUINCE / L.L.Bean / Ambercrombie & Fitch

2. Keep tweaking the classics

Basics are the hardworking backbone of a great wardrobe, but style enthusiasts look for details in shape, design and fabric that give core clothes a reset. For example, let’s say a gray turtleneck is a perennial for you. This year you might choose a shorter, boxier shape like the Abercrombie & Fitch Tuckable Easy Turtleneck Sweater in Grey ($80, abercrombie.com) that’s easy to front-tuck, or a longer style with high-low hem and ribbed sleeves like the L.L. Bean Women’s The Essential Sweater, Turtleneck in Medium Charcoal Heather ($70, llbean.com) or a cashmere splurge like the Quince Super Luxe Baby Cashmere Turtleneck Sweater in Charcoal ($150, quince.com) with modern side slits. 

spinner image & Other Stories Ribbed Knit Cardigan in Cream; Mango Belt Culotte Trousers in Medium; H&M Long Sleeved Jersey Top in Taupe
& Other Stories / MANGO / H&M

3. Know neutral colors, simple lines look luxurious

The idea of “quiet luxury” or “stealth wealth” that rejects recognizable logos and designer labels is buzzing on social media. It’s not really new for stylish women who tend to favor simple uncluttered silhouettes that are relaxed in fit and low-key colors like beige, ivory, camel and gray in addition to the usual black and navy. Some perfect examples are an ivory sweater like the & Other Stories Ribbed Knit Cardigan in Cream ($99, stories.com) worn with toned-to-match tailored pants for a monochromatic look; or tan pants like the Mango Belt Culotte Trousers in Medium Brown ($70, mango.com/us) worn with an ivory sweater and a supple jersey tee like the H&M Long Sleeved Jersey Top in Taupe and White ($13 each, ​www2.hm.com). It’s the real secret to making lower-cost clothes look posh, sophisticated and confident.

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spinner image Alex Mill Britt Work Jacket in Recycled Denim in Paprika; H&M Textured Jacket in Grey Melange; Talbot’s Military Jacket in Indigo Blue
ALEX MILL / H&M / The Talbots, Inc.

4. Let tailored jackets do the hard part

Many stylish women depend on a base “uniform” of pants or jeans and tees but never leave the house without adding a jacket. It’s that third “power piece” that counts most — sharpening even the most casual outfit, creating a pulled-together look and adding attitude. Start collecting different kinds of jackets in style, fit and fabric, and keep them in rotation. Aside from blazers, consider a spruced-up denim jacket like the Alex Mill Britt Work Jacket in Recycled Denim in Paprika ($195, alexmill.com), a crisp cropped jacket like the Talbot’s Military Jacket in Indigo Blue ($199, talbots.com) or a couture-inspired tweedy style like the H&M Textured Jacket in Grey Melange ($119, www2.hm.com). You can’t have too many.

spinner image J.Jill Sandwashed Shirttail Tunic in Brown Sugar; Fisher Ubet Suede Ballet Flats in Black; Norma Kamali Bootcut Knit Pants in Black
Jill Acquisition LLC. / Saks Fifth Avenue / Bloomingdale's

5. Insist on fashion that’s comfortable

Long before athleisure clothes and sneakers, stylish women like Coco Chanel insisted on clothes and shoes they could walk, sit and think in without complaining. Today the 50-plus style-pack still rejects new trends that feel psychologically or physically uncomfortable or are just plain silly. Instead, they look for chic knit pull-on pants like the Norma Kamali Bootcut Knit Pants in Black ($110, bloomingdales.com), long relaxed tunic tops like the J.Jill Sandwashed Shirttail Tunic in Brown Sugar ($89, jjill.com) and elegant square toe flats that don’t cram tootsies like the Marc Fisher Ubet Suede Ballet Flats in Black ($120, saksfifthavenue.com). 

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spinner image Treasure & Bond Faux Leather Midi Skirt in Black; Gap Modern Button Front T-Shirt in Black; Ann Taylor Suede Square Toe Kitten Heel Slingback Pumps in Black; a.n.a. Womens Long Sleeve Oversized Button-Down Shirt in Thea Blue Stripe
Nordstrom, Inc. / THE GAP, INC. / Ann Inc. / Penney IP LLC

6. Mix it up

Stylish women never wear “outfits” the way you see them in magazines, store displays or online sites. They buy one or two current pieces and pair them with the “oldies” in their closet for a personalized look. It’s the very individual mix of casual, tailored, dressy and sporty items — old and new — that does it. This fall style mavens are adding midi skirts in denim or faux leather like the Treasure & Bond Faux Leather Midi Skirt in Black ($79, nordstrom.com), new twists on the tee like the Gap Modern Button Front T-Shirt in Black and New Off White ($39 each, gap.com), low slingback heels like the Ann Taylor Suede Square Toe Kitten Heel Slingback Pumps in Black ($148, anntaylor.com) and oversized button-downs like the a.n.a. Womens Long Sleeve Oversized Button-Down Shirt in Thea Blue Stripe ($35, jcpenney.com) to last year’s haul. Pull out your black leather pants, balloon-sleeve sweaters and Coastal Grandma clothes — they’re about to make some new friends.  

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