Carolyn Bessette-Kennedy’s minimalist style continues to inspire fashion lovers decades after her tragic passing. Her effortless elegance combined classic pieces with modern touches, creating looks that feel as fresh today as they did in the 90s.
Let’s explore the shoe trends that would surely get Carolyn’s nod of approval if she were still gracing us with her impeccable taste today.
1. Toe-Ring Sandals
Elegant simplicity defined Carolyn’s aesthetic, making toe-ring sandals a natural fit for her wardrobe. These minimalist sandals feature a thin strap that loops around the big toe, creating a barely-there look that elongates the leg.
Fashion insiders have embraced this trend for its versatility – pair them with everything from silk slip dresses to tailored trousers. The subtle detail adds interest without overwhelming an outfit.
Carolyn would appreciate how these sandals blend form and function, offering just enough structure while maintaining that effortless vibe she perfected.
Reformation Cassandra Flat Sandal
Sustainable yet stylish, the Reformation Cassandra Flat Sandal embodies the conscious luxury Carolyn would champion today. Crafted from eco-friendly materials, these sandals feature clean lines and a barely-there silhouette that complement any outfit without competing for attention.
Modern fashionistas appreciate how these versatile flats transition seamlessly from casual daytime looks to evening events. The neutral colorways and minimal hardware align perfectly with Carolyn’s less-is-more approach.
Carolyn would likely pair these with her signature white button-downs and straight-leg jeans for weekend errands or with a sleek slip dress for dinner.
Madwell The Mila Organic Hardware Thong Slide Sandal
Architectural elements meet understated design in Madewell’s Mila Organic Hardware Thong Slides. The subtle metal hardware adds just enough interest without sacrificing the clean aesthetic that was Carolyn’s signature.
Versatility reigns supreme with these sandals – they work equally well with casual denim or more polished pieces. The slightly cushioned footbed offers practicality without compromising style, a balance Carolyn always struck effortlessly.
Fans of Bessette-Kennedy’s style will recognize how these sandals capture her knack for finding pieces that feel both timeless and current, never trying too hard yet always looking perfectly put-together.
2. Jelly Sandals
Nostalgia meets sophistication with the resurgence of jelly sandals, reimagined with grown-up sensibilities Carolyn would appreciate. Today’s versions come in smoke gray, clear, and nude tones rather than the neon brights of our childhood, aligning perfectly with her neutral palette preferences.
Fashion’s cyclical nature would amuse Carolyn, who had a knack for incorporating playful elements into her otherwise serious wardrobe. The modern jellies feature elevated details like subtle glitter or metallic finishes while maintaining clean lines.
These waterproof wonders offer practical summer footwear that doesn’t sacrifice style – a balance Bessette-Kennedy always mastered with her functional yet fashionable choices.
Loeffler Randall Rhys Jelly Sandals With Studs
Luxe interpretation meets playful nostalgia in Loeffler Randall’s Rhys Jelly Sandals. The subtle studs add just enough edge without compromising the clean lines Carolyn favored throughout her iconic style evolution.
Waterproof practicality combines with sophisticated design, creating the perfect balance of function and fashion. The translucent material catches light beautifully while the neutral tones ensure versatility with everything from casual denim to summer dresses.
Celebrity stylists note how these elevated jellies capture the essence of 90s minimalism while feeling thoroughly modern – exactly the kind of timeless-yet-current piece Bessette-Kennedy gravitated toward in her carefully curated wardrobe.
Tory Burch Mellow Mary Jane Jelly Flats
Playful sophistication defines these Tory Burch Mellow Mary Jane Jelly Flats, blending nostalgia with refinement in a way Carolyn would appreciate. The classic Mary Jane silhouette receives a modern update through translucent jelly material, creating an unexpected twist on a timeless shape.
Fashion editors have embraced these versatile flats for their ability to weather summer showers while maintaining polish. The subtle branding and clean lines honor Bessette-Kennedy’s preference for understated luxury rather than flashy logos.
Summer weddings and garden parties call for these practical yet pretty flats that combine comfort with style – a balance Carolyn consistently achieved throughout her fashion legacy.
3. Heeled Thongs
Sophisticated elevation meets minimalist design in the heeled thong trend that would surely earn Carolyn’s approval. These refined flip-flops feature slim heels that add height without sacrificing the clean lines she favored in her wardrobe staples.
Fashion insiders note how these versatile shoes bridge the gap between casual and formal, much like Bessette-Kennedy did with her effortless mixing of high and low pieces. The barely-there straps elongate the leg while maintaining that signature 90s minimalism.
Styling options abound with these versatile heels – pair them with everything from slip dresses to tailored trousers for an instantly polished look with Carolyn’s characteristic unfussy elegance.
Stuart Weitzman Rio Kitten Heel Sandal
Refined elegance meets wearable comfort in Stuart Weitzman’s Rio Kitten Heel Sandal. The modest height offers just enough elevation without sacrificing the practical wearability that Carolyn valued in her everyday wardrobe choices.
Sleek leather straps create visual interest while maintaining the clean lines and neutral palette Bessette-Kennedy favored. Fashion editors praise these versatile heels for their ability to transition seamlessly from office to evening events.
Celebrity stylists regularly reach for these sandals when creating Carolyn-inspired looks, noting how the balanced proportions and quality craftsmanship embody her philosophy that investment pieces should be both beautiful and functional.
Madewell The Deanna Thong Wedge Sandal
Practical height meets sleek design in Madewell’s Deanna Thong Wedge Sandal. The modest wedge provides comfortable elevation while the minimal straps maintain the clean aesthetic Carolyn consistently championed throughout her style evolution.
Summer weddings and garden parties call for these versatile sandals that offer stability without sacrificing sophistication. The neutral leather options align perfectly with Bessette-Kennedy’s preference for a restrained color palette that allowed her outfits to look effortlessly cohesive.
Fashion insiders appreciate how these wedges solve the grass-sinking problem at outdoor events while maintaining the polished look that made Carolyn’s style so timelessly appealing.
4. Chunky Sneakers
Sporty functionality meets fashion-forward design in today’s chunky sneakers, which Carolyn would appreciate for their blend of comfort and style. Her off-duty looks often featured athletic elements paired with more refined pieces – a high-low mix that feels thoroughly modern.
Contemporary versions offer cleaner lines and neutral colorways that align with her minimalist aesthetic. These substantial shoes create an interesting proportion play when paired with sleek silhouettes, much like Bessette-Kennedy’s knack for balancing volume in her outfits.
Weekend errands or casual brunches call for these versatile sneakers that don’t sacrifice style for comfort – a balance Carolyn consistently achieved in her effortlessly cool approach to casual dressing.
On Cloud 6 Sneaker
Technical performance meets sleek aesthetics in the On Cloud 6 Sneaker, embodying the practical luxury Carolyn would embrace today. These lightweight runners feature innovative cushioning and a clean silhouette that works seamlessly with both athletic and everyday wear.
Fashion editors have embraced these Swiss-engineered sneakers for their sophisticated approach to comfort – no sacrificing style for functionality. The neutral colorways and minimal branding align perfectly with Bessette-Kennedy’s preference for understated quality over flashy logos.
Weekend walks through Central Park or quick coffee runs call for these versatile sneakers that blend seamlessly into a curated wardrobe – exactly the kind of thoughtful versatility Carolyn valued in her clothing choices.
Adidas Sambae Shoes
Retro sportswear meets contemporary minimalism in the Adidas Sambae, capturing the effortless cool Carolyn perfected. These sleek sneakers offer a feminine update to the classic Samba, with refined proportions that would appeal to Bessette-Kennedy’s eye for subtle details.
Fashion insiders have embraced these versatile shoes for their ability to complement everything from casual denim to slip dresses. The contrast between sporty heritage and clean lines creates exactly the kind of interesting tension Carolyn cultivated in her iconic outfits.
Cultural relevance combined with timeless design makes these sneakers perfect for the woman who, like Bessette-Kennedy, appreciates both history and modernity in her fashion choices.
5. Clogs
Architectural structure meets practical comfort in today’s refined clogs, which would appeal to Carolyn’s appreciation for functional design. Modern versions feature cleaner lines and premium materials that elevate them from their humble origins to statement pieces.
Swedish heritage combines with contemporary styling in these substantial shoes that add interesting proportion to streamlined outfits. Fashion editors note how well they complement the kind of capsule wardrobe Bessette-Kennedy famously curated – simple pieces that work together effortlessly.
Weekend farmers market trips or casual office days call for these versatile shoes that offer all-day comfort without sacrificing style – a balance Carolyn consistently achieved in her effortlessly elegant approach to dressing.
Steve Madden Dutton Clogs
Sculptural form meets everyday function in Steve Madden’s Dutton Clogs, offering the kind of practical sophistication Carolyn consistently championed. The substantial wooden platform provides height while maintaining walkability – a balance Bessette-Kennedy valued in her footwear choices.
Premium leather uppers and minimal hardware create a refined take on this traditionally casual shoe. Fashion insiders appreciate how these versatile clogs add interesting texture to simple outfits, much like Carolyn’s knack for elevating basics through thoughtful accessorizing.
Transitional seasons call for these adaptable shoes that pair equally well with bare legs in summer or tights when temperatures drop – the kind of versatile investment Carolyn would appreciate.
Birkenstock Boston Soft Footbed
Understated luxury meets ultimate comfort in the Birkenstock Boston, which has transcended its utilitarian roots to become a fashion staple. The clean, unfussy silhouette and neutral suede options align perfectly with Carolyn’s preference for quiet sophistication rather than flashy trends.
Celebrity stylists note how these versatile shoes create an interesting contrast when paired with more refined pieces – exactly the kind of high-low mix Bessette-Kennedy mastered. The premium materials and thoughtful craftsmanship reflect her investment in quality over quantity.
Weekend brunches or casual Fridays call for these comfortable yet stylish shoes that have earned their place in the modern minimalist’s wardrobe – a practical luxury Carolyn would surely appreciate.
6. Platform Sandals
Substantial height meets clean design in today’s platform sandals, offering the elevated simplicity Carolyn would appreciate. Modern versions feature architectural shapes and minimal straps that create visual interest without unnecessary embellishment.
Fashion editors have embraced these versatile shoes for their ability to add drama to simple outfits while remaining walkable. The balanced proportions reflect Bessette-Kennedy’s knack for finding pieces that make a statement through form rather than decoration.
Summer soirées or gallery openings call for these statement-making yet refined sandals that embody Carolyn’s philosophy that true style lies in thoughtful editing rather than excessive ornamentation.
Free People Harbor Flatform Sandals
Bohemian influence meets clean design in Free People’s Harbor Flatform Sandals, offering the kind of unexpected pairing Carolyn often created in her iconic looks. The substantial platform provides height while the minimal straps maintain the unfussy aesthetic she championed.
Natural materials and neutral colorways ensure these statement shoes remain versatile wardrobe additions. Fashion insiders appreciate how these sandals add interest to simple summer dresses or tailored separates without overwhelming the overall look.
Vacation packing calls for these versatile platforms that transition easily from beach to dinner – the kind of multifunctional piece Bessette-Kennedy would value in her carefully curated wardrobe.
Michael Kors Nora Leather Platform Sandal
Refined elevation meets practical design in Michael Kors’ Nora Leather Platform Sandal. The substantial heel provides impressive height while the platform ensures comfort – a balance Carolyn consistently achieved in her thoughtfully curated wardrobe.
Premium leather and minimal hardware create a sophisticated shoe that commands attention through quality rather than flash. Fashion editors note how these versatile platforms complement everything from tailored trousers to summer dresses, reflecting Bessette-Kennedy’s knack for investing in adaptable pieces.
Summer weddings or evening events call for these statement-making yet refined sandals that embody Carolyn’s philosophy that true luxury lies in impeccable craftsmanship rather than obvious branding.