Understanding the Evolution of Men’s Style Across Generations
Daniel Baker, a 46-year-old investor relations expert from Palm Beach, Fla., found himself in a unique situation last winter. While rummaging through his closet, he realized that despite owning numerous clothes, none of them made him feel confident or comfortable. This moment of self-reflection is common among men as they reach significant milestones like their 30th, 40th, or 50th birthdays. The desire to reassess one’s appearance often becomes more pronounced with age, and Baker’s goal was simple: to avoid looking suddenly out of place.
Personal stylist Fiona Smart has observed this phenomenon among her clients, who range in age from 25 to over 60. She notes that men often experience what she calls “age panic” when it comes to dressing. For many, the challenge lies in maintaining a modern look while adapting to the changes in their bodies as they grow older.
Gen Z: Navigating Office Dress Codes Without Looking Like an Intern
For Gen Z men, the primary concern is figuring out how to dress for the office without appearing like an intern. Nick Clarkson, a 25-year-old financial trading associate in Manhattan, shared his observations on the pitfalls of overly flashy attire. He mentioned that seeing people arrive at work in branded hats or designer sneakers can be off-putting. Instead, he and his peers often opt for a more subdued style, such as Vineyard Vines polos, Lululemon ABC pants, and mesh navy Allbirds or black Clarks loafers.
To elevate this basic look, Smart suggests incorporating a tailored shirt with a sharp pattern, like Todd Snyder’s wide-striped Oxfords. Pairing it with a braided Ralph Lauren belt adds a touch of sophistication. A blazer from brands like Buck Mason, Alex Mill, or Suitsupply can complete the ensemble.
Elan Mizhirtsky, a 24-year-old medical student in Houston, also emphasizes the importance of avoiding flashy logos and watches that might give the wrong impression. He believes in projecting a sense of belonging and professionalism. Jason Manzano, a 25-year-old data analyst in New York, discovered that his high-key jewelry could translate into a professional setting if paired with plain shirts. His strategy involves mixing bold accessories with classic pieces, inspired by artists like A$AP Rocky.
Tarush Maniktala, a 26-year-old banking colleague of Clarkson, recommends using a company logo fleece as a safe way to distinguish oneself from interns while still looking like a legitimate employee.
Millennials: Achieving a Rich and Successful Look on a Budget
For millennials, the challenge is looking rich and successful without spending too much money. James Prager, a 35-year-old tech director, mentions the influence of shows like “Succession” on his generation’s fashion choices. He and his finance friends are obsessed with “quiet luxury dupes,” opting for affordable alternatives like Charles Tyrwhitt dress-shirts, Mango loafers, and Quince cashmere sweaters.
Kevin Coduto, a 33-year-old product engineer in Manhattan, splurges on Merz B. Schwanen tees, which he finds add a luxurious touch to his outfits. Max Bailey, a 35-year-old tech marketing executive in Rochester, N.Y., takes a different approach by investing in one pricier outerwear piece per season, such as a shirt-jacket from Willy Chavarria or Todd Snyder, which gives his overall look a premium feel.
Prager also mentions the popularity of $400 Garmin smartwatches among his peers, noting that they often claim they’re wearing them for fitness reasons but also use them to avoid buying more expensive items. For those seeking elegant, luxe-looking watches, Timex and Baume & Mercier offer affordable options.
White canvas sneakers, like Sperry’s, can be a great addition to any wardrobe, especially if kept crisp through regular washing and air drying. These shoes evoke a classic, youthful look and can be purchased for under $100.
Gen X: Finding the Balance Between Cool and Effortless
For Gen X men, the challenge is finding a style that looks cool without trying too hard. Albert Lewitinn, a 56-year-old TV executive, struggles with finding casual shirts that don’t come across as aggressively try-hard. Brian Friedlander, a 51-year-old sales VP in Manhattan, also faces similar issues with his button-down shirts from Tom Ford and Suitsupply, which now have a disco sheen finish.
Stylist Zee recommends opting for a good Ralph Lauren or Burberry polo with a solid cotton weave and a slightly thicker collar. Madewell’s low-key shirting in matte cotton is another option that exudes effortless style. Adding a relaxed bomber jacket, like Todd Snyder’s linen take, can provide a dose of no-cringe swagger.
Daniel Baker, a 46-year-old investor relations expert, has started collecting old Dior Homme pants from resale sites, appreciating their super-slim fit and classic black wool fabric. He also stocks up on cotton and linen button-ups from Athens brand 5226, which he discovered while traveling. Colman Domingo’s style, featuring prominent yet balanced collars and lapels, serves as inspiration for many older men.
Baker has also stopped wearing watches, choosing instead to go bare-wristed at exclusive clubs, which he considers a powerful move for his generation.
Baby Boomers: Dealing with Fit Issues in Pants
For baby boomers, the challenge often revolves around finding well-fitting pants. According to the Baltimore Longitudinal Study of Aging, the average male shrinks by about an inch between 30 and 70 years old, making it difficult to find pants that fit properly. Joe Rosenthal, a 78-year-old retired insurance executive in Manhattan, prefers Lululemon’s Utilitech Twill slacks, which offer a relaxed-straight fit and are easy to care for.
Richard Kind, a 68-year-old actor and comedian, found a pair of wider-leg Valentino linen pants that look sharp but move with ease. Michael Barrett, a 76-year-old nightclub designer, praises Levi’s 501s for their straight cut and waist-to-inseam options, emphasizing that classic styles remain timeless.
Worried about a flat bottom? Zee suggests opting for slimmer jeans that hug the backside and have some stretch. Brands like Wrangler offer extensive sizing ranges, making it easier to find the right fit. Harrison Ford and Bruce Springsteen serve as inspiration for those looking to maintain a sharp denim look.
