John F. Kennedy Jr.’s effortless ’90s aesthetic is experiencing a resurgence, fueled by the recent FX series “Love Story” dramatizing his romance with Carolyn Bessette Kennedy. His style wasn’t about chasing trends, but a distinctive blend of American polish and casual ease—a formula many now seek to replicate.
Mastering the Core Elements
JFK Jr.’s look revolved around simplicity: soft tailoring, dark denim, and elevated basics. Unlike stiff, structured suits, his favored Armani and Calvin Klein pieces had an oversized fit and relaxed drape. Restraint was key—no excessive accessories, just well-fitted garments and confident posture.
The foundation of his style lies in:
- Soft tailoring: Opt for lightweight fabrics with natural shoulders over rigid structures. A navy blazer, charcoal suit, or knit tie are excellent starting points.
- Dark, straight-leg denim: Mid-rise, unfussy jeans in a dark wash provide an intentional, mature look. Avoid skinny fits; Kennedy’s denim had structure.
- Crisp white shirts: Pair a relaxed Oxford or poplin shirt with denim or tailored trousers for a clean, masculine aesthetic. Think Nantucket weekend, not boardroom formality.
Finding the Right Pieces
Replicating this style doesn’t require breaking the bank. Vintage shopping on platforms like eBay, Depop, and Poshmark is an effective, sustainable way to find authentic ’90s pieces. A simple search for “Vintage Mens Ralph Lauren Sweater” or “Vintage ’90s LL Bean” yields a vast marketplace.
Adding Personality and Layering
Kennedy’s style wasn’t afraid to mix in unexpected elements: a Kangol cap, a beret, or even a sweatband could elevate an outfit. The key is mixing elevated basics with casual pieces—a sport coat with jeans and a baseball cap, or sweatpants paired with a cable-knit sweater.
Layering was another hallmark. Vests, scarves, sweaters, and hats were used strategically to add depth and interest, especially in colder weather. Thrifting accessories is an easy way to experiment without significant investment.
Finishing Touches
Complete the look with:
- Classic penny loafers : These elevate an outfit instantly and provide a sense of intentionality.
- Sunglasses: Tortoiseshell Persols or blacked-out oval frames add mystery and a touch of privacy.
- Consistency: Kennedy’s discipline in repeating pieces and staying true to his taste is what made his style iconic.
Ultimately, JFK Jr.’s influence is not about having more clothes, but refining what already works. His look stands as a testament to timelessness and simplicity, a refreshing contrast to today’s fast-paced trends.
