Love Story Style: Inspiration from Carolyn Bessette-Kennedy’s Effortlessly Chic Wardrobe
If you’ve been watching Love Story, you already know the series draws clear inspiration from the real-life minimalism of Carolyn Bessette-Kennedy, a woman whose 1990s wardrobe continues to shape how we define understated or quiet luxury today. As a stylist, what stands out isn’t just the simplicity, it's the discipline. Clean lines. Neutral palettes. Intentional proportions. Nothing excessive, nothing accidental. Here are three looks inspired by the show that feel especially relevant right now and are easy to transition into real life.
1. The Elevated Casual
The oversized white dress shirt, jeans, and loafers are the uniform that built millions of Pinterest boards, and it works because it’s rooted in proportion. An oversized, crisp dress shirt paired with straight-leg denim creates that effortless high-low tension. It feels borrowed but controlled. Relaxed but polished. The loafers ground the look and keep it from drifting into “just ran out” territory. The key is restraint: clean-wash denim, minimal hardware, and a structured loafer (not overly chunky).
Tara’s Style Edit: The shirt should be intentionally oversized, not sloppy. If it pulls at the buttons or collapses at the collar, it’s wrong. I often recommend sizing up one full size and tailoring the sleeves slightly, if needed.
2. Modern 90s Contrast
A chic strapless dress with a cropped leather jacket and low-heeled Manolo Blahnik mules is where minimalism meets personality. The fit and tailoring of this Toteme strapless dress are sleek and sculpted fitted but not tight. The architectural dress, styled with the yellow leather jacket, interrupts that restraint with confident ’90s energy. That cropped proportion is critical. It visually shortens the torso and sharpens the waistline, especially over a strapless silhouette. The low-heeled mules keep the look refined and grounded instead of veering into eveningwear.
Tara’s Style Edit: If you’re wearing strapless during the day, structure is everything. Look for internal boning or a built-in corsetry element so you’re not adjusting it every five minutes. And keep accessories minimal, let the jacket be the statement.
3. Sophisticated Everyday
This outfit formula is elegant, confident, and clean. Tailored trousers with a matching cardigan set, ballet flats, and an oversized hobo bag are the quiet luxury blueprint. Tailored trousers create a strong foundation. A fitted shell keeps the lines clean, and a soft cardigan set layered over the shoulders or worn buttoned adds dimension without bulk. Signature ballet flats bring softness, while the large hobo bag introduces ease and practicality, offsetting the tailoring so the look doesn’t feel too corporate.
Tara’s Style Edit: Pay attention to fabric weight. If the trousers are structured, the cardigan should be fine-gauge, not chunky. Balance is what keeps this look elevated instead of frumpy. And always steam your garments - wrinkles ruin the minimalism aesthetic.
