What Great Style Looks Like at Every Age

Four fashionable women, ages 39 to 67, show off their style; plus, their favorite beauty buys

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Rachel Roy, 39, Fashion Designer

On her personal style “Classic with a twist. I’m most comfortable in simple, timeless silhouettes, but I like a bit of edginess to make the look unique to me.”


On good tailoring “Spend a little extra to get your clothes properly tailored. You will feel more confident in clothes that fit well—and it’s worth the cost. Better to own three amazing pieces that fit perfectly than a closetful of just-OK items.”


On her dressing guidelines “I believe in balance. With tight leather pants, I wear an oversize men’s shirt. Baggy pants look best with a tight turtleneck. Even in this outfit [photo above], I chose deep-plum Manolo Blahnik shoes to balance the vivid pink dress.”


On what I’m wearing “I picked this bright color because it energizes me and everyone I meet—and I get to carry that good energy with me all day. My necklace is from Jennifer Meyer, and it is engraved with my daughters’ names.”

Ari Michelson

Rachel's Top Beauty Buy 1

Estée Lauder nail lacquer in Pure Red ($20; esteelauder.com)

Bryan McCay

Rachel's Top Beauty Buy 2

Chanel No. 5 body lotion ($50; chanel.com)

Bryan McCay

Rachel's Top Beauty Buy 3

Jo Malone red roses cologne ($55; jomalone.com

Bryan McCay

June Ambrose, 41, Stylist to Stars like Mary J. Blige and Alicia Keys

On three words that describe her style “Daring. Sassy. Classy.”


On why she’s not the uniform type “Never! I always prefer to be unpredictable and uncontrived.”


On my big spring project “I created a shoe collection for HSN that will inject energy into a closetful of classic clothes. The shoes are all wearable and versatile, but each pair has been designed with an unexpected twist to liven up your look.” [In the photo above, June is wearing Onassis wedges, $90 from her HSN collection.]


On her one conservative concession “When it comes to jewelry, I like timeless pieces such as my diamond studs. I collect cuffs. I might wear chandelier earrings to the opera, but in general I prefer simple jewelry. I make style punctuations in other places.”


On her signature accessory “I am known for wearing a super-high heel. I am vertically challenged, so I love a six-inch shoe from designer Charlotte Olympia. It gives me confidence.”


On her beauty routine “I’m somewhat makeup illiterate, but I’ve learned. My everyday staples are false lashes, tinted moisturizer and a little bronzer. And I’m big on what I call glama-flage: hat, big sunglasses and turbans. They hide a whole host of sins.”

Ari Michelson

June's Top Beauty Buy 1


1  False lashes, custom cut by her makeup artist

Jens Mortensen

June's Top Beauty Buy 2

Urban Decay naked skin foundation ($39; sephora.com

Bryan McCay

June's Top Beauty Buy 3

Nars bronzing powder in casino($36; sephora.com)

Bryan McCay

Angelina Chen, 52, Senior Director of Circa in New York and Hong Kong

On her style mantra “Aim to look simple, elegant and effortless.”


On her favorite labels “Calvin Klein, Prada, Céline—and Zara.” On what she’s never without “I have four watches, and I rotate them to match the jewelry I’m wearing.”


On outfit selection “I look at my calendar to select what to wear. For example, if I will be running between appointments, I favor my Valentino shoes [in photo above] because they have a low heel and I can get around without pain.”


On what you wear now that you couldn’t at 25 “I wear more fine jewelry than I did then. And serious pieces look more appropriate at this age.”


On her favorite recent purchase “I splurged on a pair of diamond drop earrings [in photo above], and I wear them during the day, which is unexpected.”


On how her style has changed “When I reached 40, all the clutter of youth had to go. My look has been simplified ever since. I gravitate toward investment pieces now—things to last me at least three seasons.”

Ari Michelson

Angelina's Top Beauty Buy 1

Shiseido accentuating cream eyeliner in black ($26; shiseido.com)

Bryan McCay

Angelina's Top Beauty Buy 2

Chantecaille lipstick in trillium($34; chantecaille.com)

Bryan McCay

Angelina's Top Beauty Buy 3

Bulgari jasmin noir($98; sephora.com)

Bryan McCay

Jaclyn Smith, 67, Actress and Fashion and Beauty Entrepreneur

On not messing with a good thing “I have always been into classic, comfortable clothes. If it doesn’t feel good, I’m not going to wear it.”


On her signature outfit “I am a Texas girl, and I feel most comfortable in jeans or leggings paired with a sweater or T-shirt. I have dozens of pairs of jeans—from my own line and also Current/Elliott, J Brand, Rag and Bone. And I love Balenciaga leggings.”


On one fashion mistake she’s made “When my kids were small, we were always racing around, running late. And I never took the time to change my purse. I carried the same bag, jammed full of kid stuff, around with me every day. I’m sure I ruined many an outfit that way.”


On meaningful baubles “Most of my jewelry was given to me by loved ones, and it tells the story of my life. My mother gave me a necklace with two diamonds to represent my two kids, and I wear it almost daily.”


On what she’s retired—and revived “My tank-tops-and-short-shorts days are over. But I do think I look better in leggings now than I did in my twenties; I fill them out better.”


On her biggest indulgence “Handbags. Perhaps because I once didn’t appreciate purses enough, I now love them. I have some beautiful Céline bags, I adore the Hermès Kelly, and I just got a tiny cream-colored Chanel.”

Ari Michelson

Jaclyn's Top Beauty Buy 1

Giorgio Armani luminous silk foundation ($60; giorgioarmanibeauty-usa.com)

Bryan McCay

Jaclyn's Top Beauty Buy 2

OPI Nail lacquer In Don’t Burst My Bubble($9; ulta.com)

Bryan McCay

Jaclyn's Top Beauty Buy 3

Guerlain L’art et La Matiére, cuir beluga eau de parfum ($250; nordstrom.com

Bryan McCay

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