JFK Jr’s Style: How ‘Love Story’ & 90s Fashion Are Making a Comeback

The buzz around the FX series Love Story isn’t just about a captivating retelling of John F. Kennedy Jr. And Carolyn Bessette Kennedy’s romance. It’s ignited a surprisingly potent wave of menswear inspiration, echoing a similar phenomenon sparked by Mad Men years ago. Here in Chicago, where the winds off Lake Michigan seem to carry a certain classic sensibility, the display’s impact is particularly noticeable. It’s not just about replicating Paul Anthony Kelly’s on-screen wardrobe – though many are trying – it’s about a broader shift in how men are approaching style, a move away from overly casual trends and towards a more considered, sophisticated aesthetic.

The Return of Effortless Style

RoseMarie Terenzio, JFK Jr.’s former assistant and co-author of JFK Jr.: An Intimate Oral Biography, offers a glimpse into his personal style. It wasn’t about extravagance, but rather a quiet confidence. He appreciated quality – a green velvet Gucci suit for a Christmas party, a touch of Kiehl’s Silk Groom – but wasn’t driven by a need for a vast collection. This resonates with a growing desire for mindful consumption and a rejection of rapid fashion, a sentiment increasingly prevalent among Chicagoans. The show highlights a similar ethos, portraying JFK Jr. As someone who valued substance over showiness, a quality that appeals to a generation seeking authenticity.

The comparison to Mad Men, as noted by GQ’s Rachel Tashjian, is apt. Both shows tapped into a nostalgic yearning for a bygone era of polished presentation. Mad Men, however, arrived during a period when menswear was still recovering from the grunge and hip-hop influences of the 90s. It offered a blueprint for a return to tailoring, to classic silhouettes, and to a more formal approach to dressing. The impact was significant, influencing brands like J.Crew with their Ludlow suit and designers like Thom Browne with their innovative takes on traditional menswear. The current wave, fueled by Love Story, feels different. It’s less about strict adherence to a specific aesthetic and more about incorporating elements of classic style into a modern context. It’s about finding that balance between sophistication and ease, a look that feels both timeless and contemporary.

Chicago’s Unique Style Landscape

Chicago, with its architectural heritage and its reputation for a pragmatic yet stylish population, is a particularly fertile ground for this trend. The city’s menswear scene, anchored by institutions like Nordstrom on Michigan Avenue and independent boutiques in neighborhoods like Wicker Park and Lincoln Park, is responding to the demand for elevated basics and classic pieces. The influence extends beyond clothing, impacting grooming habits and accessory choices. A recent uptick in demand for classic fragrances and well-crafted leather goods at stores like Marshall Field’s (now Macy’s) suggests a broader embrace of a more refined aesthetic. The Art Institute of Chicago, a beacon of cultural influence, often hosts exhibits that subtly reinforce this appreciation for timeless design and craftsmanship.

The timing is also noteworthy. As the world emerges from the pandemic and a period of prolonged casualization, there’s a palpable desire to reconnect with a sense of normalcy and to express oneself through clothing. The return to office life, even in a hybrid model, has further fueled this trend. Men are seeking clothing that conveys confidence and professionalism, but without sacrificing comfort or individuality. Here’s where the lessons from Love Story – and from JFK Jr.’s own style – prove particularly valuable. It’s about finding pieces that are versatile, well-made, and that reflect a personal sense of style.

Navigating the New Menswear Landscape in Chicago

Given my background in fashion journalism and trend forecasting, if this shift towards a more sophisticated menswear aesthetic impacts you here in Chicago, here are three types of local professionals you might find yourself needing to consult:

Personal Stylists Specializing in Classic Menswear:

Look for stylists with a proven track record of working with clients who appreciate timeless style. They should be able to help you build a versatile wardrobe based on your body type, lifestyle, and personal preferences. Crucially, they should demonstrate a deep understanding of fabrics, tailoring, and fit. Avoid stylists who push trendy or overly branded items; focus on those who prioritize quality and longevity.

Master Tailors with Bespoke Experience:

A well-tailored suit or sport coat can elevate your entire look. Seek out tailors who offer bespoke services, meaning they create garments from scratch based on your individual measurements and preferences. Don’t settle for alterations alone; a truly bespoke garment will fit you perfectly and flatter your physique. Check online reviews and ask for referrals from trusted sources.

Wardrobe Consultants Focused on Sustainable Fashion:

If you’re interested in building a more sustainable wardrobe, a wardrobe consultant can help you identify high-quality, ethically sourced pieces that will last for years. They can also advise you on how to care for your clothing properly, extending its lifespan and reducing your environmental impact. Look for consultants who are knowledgeable about sustainable brands and materials.

Ready to find trusted professionals? Browse our complete directory of top-rated stylists, tailors, and wardrobe consultants in the Chicago area today.