Header image of Yamilca Rodriguez for Age-Defying Fashion story.

There are those who believe that there are unspoken age limits on fashion. That edgy, sexy or avant-garde looks are best left to anyone under 40, while those heading into midlife and beyond should be settling into a stylistic safety zone. The five women photographed here reject that notion and demonstrate the rejuvenating power of dressing by your own rules.

Styled & Written by Christine Fellingham | Photographed on location at Louisville Thoroughbred Society by Kylene White

You don’t have to be 22 years old or a professed fashionista to know how to turn heads or make clothes work for you. The stunning women photographed on these pages are evidence that the wisdom gained with age can translate into cutting-edge, inimitable personal style. While each of them has a completely different fashion philosophy, they share one thing in common: They know who they are and they dress the part.

Getting them outfitted for this shoot was a breeze. They speed-browsed the racks of curated garments, instantly eyeing what would work and just as quickly rejecting what wouldn’t. While they’re not trend averse, they also not trend-obsessed. Each of them are magnetically drawn to clothes that are an authentic representation of the woman they are in the world.

These fashion icons all agree that wearing what makes you physically or emotionally uncomfortable is a rookie mistake that they no longer make, and that taking pleasure in how they put themselves together is their secret to reverse aging. The modern holiday looks they model here prove that great style starts with breaking the rules and only improves over time.

Detail image of Yamilca Rodriguez for Age-Defying Fashion story.

Jonathan Simkhai vegan leather dress, $745, at Rodeo Drive.

Yamilca Rodriguez, 54, CEO of Bespoke Personal Branding

How she broke the rules: No one is thinking about age when they see this curvy, leather cocktail dress that fits and flatters Yamilca like it was made for her. The sophisticated loden hue lends it more elegance than, say, a studded biker iteration.

Where she developed her fashion sense: “As a young girl growing up in Venezuela, my first love was fashion. I took sewing lessons as a teenager and dreamed of being a designer, but my practical side won out and, instead, I majored in industrial design at University of Cincinnati – eventually working for Proctor & Gamble designing product packaging. I traveled the world and dressed like a designer– in black, architectural clothes with interesting accessories or details like a great necklace, shoe or purse. That experience really shaped my look.”

“I dress based on how I feel, what I’m doing and what I want to portray to the world.” Yamilca Rodriguez, 54, CEO of Bespoke Personal Branding

Her style mentors: “I’ve always loved Carolina Herrera. We lived in the mountains in Venezuela, but I would visit Caracas and go to the Carolina Herrera store and I was just mesmerized. The clothes were timeless and simple, but the details were stunning. I am also fascinated by Coco Chanel. Her clothes were a reflection of who she was. I always aspire to that.”

How she describes her personal style: “I wear clothes that are a reflection of who I am and how I want to feel. I still gravitate towards sculptural shapes but I am wearing more color right now. In my new venture, I help people identify and project their personal archetypes in everything from their professional branding to their own wardrobes. I believe that great style starts with being comfortable in your own skin and is an expression of your true self.”

Detail image of Nancy Deville for Age-Defying Fashion story.

Jumpsuit, Nancy’s own. Iris Setlakwe blouse, $245, at Rodeo Drive.

Nancy Deville, 72, Executive Director of Prison Yoga + Meditation

How she broke the rules: A chic Parisian jumpsuit was the starting point for a look that’s both on trend and timeless. Nancy bought this black staple in Paris, and it pairs perfectly with an of-the-moment white silk blouse with billowy, big-volume, pleated sleeves.

Where she developed her sense of style: “I started getting interested in fashion when I was 14, in 1964. Women had just escaped strangulation by girdles, so fashion was evolving. I lived in Japan near Tokyo. Having long blonde hair got me modeling jobs. I was all Twiggy and the British influence. In 1968, when I was eighteen, I went overland to India on the Hippie Trail and my whole fashion sense took a vacation. I went natural. I was probably mid-20s before I got interested in fashion again. I felt most comfortable in classic clothing. That became my style and I’ve always felt most like myself in tailored, chic looks with a touch of romantic.”

“Monochromatic palettes are my style. Whenever I buy something bright, I wear it once, uncomfortably, then it migrates into the donation bag.” — Nancy Deville, 72, Executive Director of Prison Yoga + Meditation

How her style evolved: “When I got into my 60s,  I started really feeling uncomfortable showing skin. This was a challenge with the traditional, tailored look, because it can appear severe and masculine if you’re not careful. So my style had to be completely rethought. We’ve had some recent fashion trends with big clunky shoes, for example. That does not work. I’m more Manolo Blahnik than Doc Martin, or ballet slippers rather than Nikes. I will leave the house without makeup but never, ever without lipstick. I wear two shades, red or nude– nothing in between.”

Shopping strategies? “I never, and I mean never go out and just buy a bunch of things. I have so many clothes that it’s not really necessary. What is essential is cleaning out my closet. I force myself to clean out my closet at least once– if not twice– a year and try things on. If I don’t, I forget what I have and how to style it.”

Detail image of Terri Page for Age-Defying Fashion story.

Milly vegan leather blazer, $475, and pants, $425, at Rodeo Drive.

Terri Paige, 58, CEO of Medical Transformations Center, mother of eight

How she broke the rules: A pink leather pantsuit is hardly a play-it-safe option, but pink is a favorite color (when she isn’t wearing black) and this suit just spoke to Terri, so she went for it. She kept the look simple and uncluttered, skipping a blouse for a hidden tank top and opting for earrings as the only accessory in a singular fashion statement.

Where she developed her sense of style: “I have always loved clothes and shopping. It’s a passion of mine. Growing up, I poured over Glamour magazine – paying attention to every little detail. I would look at the fashion and think, ‘How am I going to imitate this?’ I would go to The Fashion Shop and recreate the looks for less.”

“Spend more on staples and less on trends. Buy the best pair of black pumps you can afford. You’re going to wear those suckers forever.” — Terri Paige, 58, CEO of Medical Transformations Center

Her style mentors: “My dad was from the Philippines. He was a natty dresser and he loved to shop. My parents divorced when I was a young teenager and he was in charge, but he was a doctor and he was busy. We grew up in a small town in Western Kentucky and my sisters and I had charge accounts all over town and we inherited that bug of his that we just liked to shop. Not that I wanted to own everything, but we enjoyed the fun of putting things together. It wasn’t extravagant; we would buy Faded Glory clothes and Bass shoes. I definitely got my passion for style from him.”

Her style philosophy: “I’m kind of old school. When I travel, I dress up. When I see people wearing their pajamas out, I can’t imagine doing that. I tell my kids to err on the side of overdressing. You want to present yourself in a way that is respectful to someone else.”

Her fashion mottos or mantras: “Dress to the level that you aspire to. So, if you’re in corporate America, look several layers up. Level up a little. And don’t spend a ton of money on trends. Spend your money on staples. You’d be amazed at what you can find at good consignment stores like Sassy Fox and Belle Monde. Pass up the Old Navy and get the St. John’s. Think cost per wear.”

Detail image of Valerie Combs for Age-Defying Fashion story.

INC vegan leather jumpsuit, $109.50, at Macy’s Oxmoor. Denise Nader 24k gold-plated cuff (in hair), $500, at Rodeo Drive.

Valerie Combs, 62, University of Louisville Director of Development and Hall of Fame basketball player, retired flight attendant for TWA/American, mother of one

How she broke the rules: Tall heels, tall hair and an elongating leather jumpsuit make Valerie Combs – a six foot tall stunner– stand out. And she wouldn’t have it any other way.

Where she developed her sense of style: “I’ve always worn things that draw attention. I love hats, jewelry, bold accessories. Being a jock my whole life, I always wanted to show people that I love a good sweat, but I like looking good too. I was also a flight attendant for 29 years and it was mandatory to wear inch-and-a-half heels. You would have the heels and the uniform on and you’d strut through that airport, pulling your luggage. You’re with the crew and all eyes are on you. I loved that feeling of being all dressed up and turning heads. I still do.”

“Get the sweats off. Represent yourself in the same way all the time so you don’t get caught not looking your best.” — Valerie Combs, 62, University of Louisville Director of Development

Her style influences: “Nobody influenced me. I just wear what I like and I’ve always liked what’s different. My parents did bring me up to have confidence and that helps.”

Her style philosophy: “Always look like you’re going for an interview because you never know who you’re going to see. Even if I have jeans on, I throw on a blazer. This is Louisville and you can run into people anywhere. I don’t like to be out of character.

“I am known for my accessories. I have a hat wall in my house with maybe thirty hats. I love a tam in the wintertime in a bold color like fuchsia – cocked sideways on your head. And every time I go to the women’s basketball games, they look at my shoes. You can wear a mediocre outfit, but the right shoe turns your outfit into something special.”

Fashion mottos: No teeny heels! My daughter and I laugh at kitten heels. We would never do that. Heels make me feel empowered. I put on a pair of heels and strut into a room and it makes people’s heads turn and they’re thinking, ‘She’s a tall drink of water.’ And, I’m thinking, ‘Yeah. I am!’

Detail image of Djenita Pasic for Age-Defying Fashion story.

Velvet blazer, $55, and pant, $45, at Mamili. INC blouse, $69.50, at Macy’s Oxmoor.

Djenita Pasic, 63, attorney, mother of one, grandmother of two

How she broke the rules: This turquoise velvet pantsuit could scream trendy, but by wearing it with classic pumps and an elegant leopard shirt, Djenita makes it all her own.

Where she developed her sense of style: “I was born in Europe (Bosnia), where people care a lot about clothing. You walk in the city all the time, so you see people and you are being seen. You dress up every time you leave the house. Your sense of style becomes ingrained and subconscious.”

“My dressing is quick and simple. It never takes more than 15 minutes.” — Djenita Pasic, 63, attorney

Her style mentors: “First, it’s my mom, who at 89, is literally a fashion icon in her own right. To this day, she dresses up every morning. Now, she wears mostly a pair of pants and a top or vest, but she always has some discreet jewelry – earrings, a bright scarf or bandana, a touch of lipstick. She still dyes her hair. Because of all of that, she looks much younger. Very often, she would tell me, ‘Why don’t you go put some makeup on?’ She’s right! There is a difference when you put makeup on. You feel better.

“Then there is my dad. He is 88 and has beautiful white hair. He goes to a salon and has his eyebrows dyed every two weeks. He is still quite stylish. They have both been huge influences on how I present myself to the world.”

Her philosophy about getting dressed: “My philosophy is quite simple: I do it on a whim. I do not fret much. I have one purse per season and I carry it for five or six years.  I do not have many clothes or shoes at all, but everything seems to click well together. I’ve had some favorite pieces for 20 years and they still look great.”

Style mantras or mottos: “Yes! If you have any doubts, just don’t wear it. Never buy any expensive brand; give that money to charity. Style does not have anything to do with money. Look as good as you can in every setting. You want to show that you care about yourself and those around you.”