The Shopping Trick Women Over 50 Swear By

Four industry insiders share their insights about shopping and style.

Originally Published: 
We may receive a portion of sales if you purchase a product through a link in this article.

Diana Vreeland once quipped that "age is totally boring" — I hate to deviate from the legendary editor whom I invariably turn to for inspiration, but I happen to think age is pretty fascinating. More specifically, the experience of aging and how it relates to self-expression. As children, there are no rules when it comes to fashion. As we grow up, our purchases become influenced by what others are wearing and the general zeitgeist. Once you reach a certain degree of adulthood, your tastes are a byproduct of life experience. Fashion items that women over 50 invest in can reflect their careers, hobbies, motherhood, finances, and travels (among several other factors). Cultivating personal style comes with time and aging, it shouldn't be rushed.

Naturally, these sensibilities arrive at different points in each individual's life, but for many women who have reached the milestone of 50, a honed sense of self and style is generally under the belt, so to speak. In the interest of further exploring this relationship with age and style, I tapped four industry insiders to share the lens with which they view fashion. Find out how they approach their wardrobes, where they shop, their take on trends, and a bevy of interesting insights I promise you won't want to miss. Get a pen!

We only include products that have been independently selected by The Zoe Report's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Women Over 50 Fashion Advice: Brick & Mortar Can't Be Replaced

Fashion e-commerce sales are skyrocketing but the immersive experience of in-person retail still resonates. “Exploring brick and mortar has always been my joy; to go around to little shops and discover new things,” stylist and entrepreneur Linda Rodin shares with me. “Off-the-beaten-track types are my favorites.” For House of Aama Co-founder Rebecca Henry, though online shopping offers ease and flexibility, “nothing compares to the brand experience in a brick and mortar store and the ability to touch and feel the garments,” she says. “I shop in stores offering new items and vintage for those special one-of-a-kind finds.” Stylist Jeanne Yang nods to the advantage of trying on clothing as an essential part of the process, particularly when it’s pre-loved. “Recently, I have loved getting vintage at Decades and The RealReal for the well-priced treasures you can find.”

Women Over 50 Fashion Advice: Investments Are Paramount

Jeanne Yang Photo: Ruven Afanador

You probably read quite a bit about investment pieces — fashion items that require financial planning with the trade-off of wearing them for years (even decades) to come. Unsurprisingly, all of the women I spoke with were able to quickly recall investments that enrich their personal style. Joh Siff, a brand adviser with over 25 years of industry experience including top positions at Prada and COMME des GARÇONS, points to outerwear as a key investment category.

“A long pea coat in heavy wool melton, a long tweed coat with a silver technical lining, and several bonded leather coats,” are all purchases Siff has made and loves. “I think investing in top quality outerwear, shoes, and accessories that you take good care of will last forever.” This sentiment also rings true for Yang. “I saved and purchased a cashmere Pallas winter coat that is my favorite wardrobe item I have ever purchased,” she shares. “It is warm, stylish, and will look great forever — so worth that financial investment.”

Not all investment items must be staples, however. For Rodin, her prized piece isn’t a tailored blazer or leather loafers. “My favorite investment piece is a pair of silver Chanel boots that I wear and cherish,” she says. “They are timeless and the most comfortable.” Her exuberant pick brings up an important point: growing older doesn’t equate to a singular sense of style. Over-50 fashion can’t be classified as one specific aesthetic, and it shouldn’t be. Rather, the thing to ascertain from these women is the experience of knowing oneself and dressing accordingly with certainty and ease.

Women Over 50 Fashion Advice: Understand Your Relationship With Trends

Rebecca Henry Photo: Courtesy of House of Aama

Rodin has been wearing Levi’s since she was five years old and white boots since her teen years. “I don’t really follow trends,” she explains. Neither does Siff. “No. Never. I prefer to invest in quality, luxury, timeless pieces and from brands where I feel a ‘connection’ to the vision and aesthetic,” she explains.

For Henry and Yang, however, trends aren’t off the table, which might be attributed to their career paths: designer and stylist. "I am always aware of trends but don’t jump on them for myself unless it matches my aesthetic and comfort level,” Yang explains. Henry describes her personal style as “nerd girly chic with a splash of ethnic” and will add trending items from time to time, so long as they fit within her style code.

Women Over 50 Fashion Advice: Support Emerging Talent

Joh Shepley Siff Photo: Jon Irvin / Alejandra Alonso Rojas

Siff stresses the importance of investing in the next generation of designers making a positive impact. A few examples she offers include Slow and Steady Wins the Race, Alejandra Alonso Rojas, Ashlyn, Micoli, Considered Objects, and Danielle Fichera.

“Each [of these designers] make products with a commitment to eliminating and reducing wastage. They source materials that are organic or metal-free, they upcycle, repurpose, recondition, and so forth,” she explains. “I also have deep respect for the independent specialty retailers who have responded to the challenges of our times and curate with energy and vision. I support young designers who occasionally open up their studios or showrooms for pre-ordering.”

Siff’s emphasis was spurred by becoming more inwardly focused, as she puts it. “I am more conscious now about communicating positively through the choices of what I wear. I like to uplift and inspire people around me through my style,” she explains. “I dress and shop with more awareness and confidence. Many designers and brands are dedicated to finding solutions to the crises facing our planet and humanity. I find it heartening to discover and support brands that are leading change for the good.”

Women Over 50 Fashion Advice: Identify Key Wardrobe Pieces

Courtesy of Linda Rodin

Depending on where you live, your career, your finances, and myriad other factors, key wardrobe pieces may differ. Whatever the case, all four women agree that identifying your staples is worthwhile. For Henry, layering is key — citing turtlenecks, short sleeve sweaters, and puffer coats as essential. “Hair accessories such as headbands and hair clips are a big must for me as I wear them every day,” she adds. Rodin is a fan of all things denim — both vintage and designer, “and my favorite coats — all fake fur — Dries Van Noten white shag coat and a wonderful Balenciaga black kind of car coat length fake monkey fur jacket.” Jang in turn has a handful of essentials she wears over and over again. “Custom Common Project pink basketball sneakers, Pallas black silk tuxedo coat, Khaite black backless cocktail dress, Mr. Porter heather grey cashmere sweater, Stella McCartney silk tuxedo shirt, Holmes and Yang army green suede safari coat, and Crippen jeans.” And while Siff wears menswear-inspired trousers and embellished skirts for every day, she also loves an occasion to dress up, citing “dresses which tend to be long, dramatic, and easy to walk in, minimalist knitwear, and a collection of shoes, mainly brogues and men's styled lace-ups with a long last in a range of colors for year-round wear.”

This article was originally published on