Building a Carolyn Bessette-Kennedy Inspired Summer Capsule Wardrobe

Carolyn was an extremely private person, and tie that to a time way before social media, and all we really know about her are the stories those close to her shared, and her impeccable wardrobe.

Can we all afford a Carolyn Bessette-Kennedy wardrobe?

No, probably not.

But many of us can bring elements into our own wardrobes that are inspired by her style.

There’s a reason Carolyn Bessette-Kennedy’s name still surfaces when we talk about timeless style.

She’s the woman who could walk down the street in a simple white tank and look like she was headed to a gallery opening in SoHo.

Her wardrobe was never loud, rarely trend-driven, and always, always refined.

Even in summer, when fashion can so easily lean into chaotic prints or awkward seasonal trends, Carolyn stayed true to a polished, minimalist core.

She made simplicity feel luxurious and sensual, without ever trying too hard. And that’s the magic we’re channelling here. Or at least attempting to.

This guide is about crafting a summer capsule wardrobe that embodies Carolyn’s ethos: cool without the effort, elegant without the excess

Who Was Carolyn Bessette-Kennedy, and Why Does Her Style Still Matter?

Before she became American royalty as the wife of John F. Kennedy Jr., Carolyn Bessette was a Calvin Klein publicist, a role that shaped much of her minimalist aesthetic.

Working behind the scenes at one of the most influential fashion houses of the ’90s, she absorbed the essence of clean lines, neutral palettes, and understated luxury.

What set Carolyn apart was her ability to dress in a way that felt both aspirational and accessible.

She didn’t need logos, trends, or Instagram to validate her choices. She understood silhouette, proportion, and quality.

Her look was rooted in intentional simplicity, which is exactly what makes it so compelling today, especially in an era that often feels visually noisy.

Building the Capsule: What to Include

This isn’t about owning more; it’s about having the right pieces on rotation. Below are the essential Carolyn-coded summer staples—each piece is functional, elegant, and made for repeat wear.

The Perfect White Shirt: Oversized, slightly sheer, and made of breathable cotton or silk. Worn loose over a slip dress or half-tucked into tailored shorts.

Minimalist Slip Dresses: Full-length or midi silk slip dresses in black, ivory, or champagne. Ideal for warm nights, paired with flat leather sandals.

Tailored Trousers in Light Fabrics: Slouchy but structured trousers in linen or lightweight wool. Pair with a fitted tank or crisp tee.

Vintage Jeans: Specifically the Levi’s 517, which is a bootcut and her favourite.

Note: When buying vintage jeans, compare the measurements to a pair you love the fit of which is 100% cotton and freshly washed. This will give you the best indication of fit.

Prada Shoulder Bag: Perhaps her most iconic, lightweight, practical, and barely branded.

Black Leather Top-Handle Bags: Structured, architectural, and clean. Often Prada or Gucci, but never flashy.

Brown Leather Totes: Mid-sized, slouchy, and quietly luxe.

Envelope Clutches, Mini Bags, and Vintage: Simple silhouettes, often in satin or leather, for evening.

For casual time away, she was often seen with her large L.L. Bean tote, which they still sell today, and you can even get monogrammed.

Update the Cut, Not the Concept
Carolyn loved a long-line slip dress, but today’s silhouettes might offer more freedom.

Think asymmetrical hems, open-back detailing, or built-in structure at the bust. Look for elevated cuts in the same neutral palette, but with subtle tailoring that adds interest.

Play with Texture
To modernize a monochrome look, combine contrasting textures: a raw linen pant with a silk tank, or a crisp cotton button-up layered over a ribbed knit tube top.

Carolyn didn’t mix many fabrics, but today’s take on minimalism allows for more tactile dimension.

Add Just-One Statement Piece
Introduce an unexpected pop: a sculptural bag, bold flat shoe, or oversized sunglasses in tortoiseshell or clear acetate.

This keeps the look minimal, but gives it a 2025 edge. It’s the minimalist’s answer to maximalist dressing. One great piece, not five.

Make It Genderless
Carolyn’s wardrobe was inherently androgynous with blazers, trousers, and crisp shirts, but the modern update embraces even more gender-fluid tailoring.

Borrow from the men’s section (or just the men in your life) for oversized linen shirts, wide-leg suiting pants, and boxy tanks.

Layer with Modern Utility
Incorporate functional, urban pieces that blend seamlessly: a crossbody nylon bag (à la The Row’s banana bag), fisherman sandals, or updated cargo trousers in elevated materials.

These details add a contemporary slant while still feeling neutral and polished.

Subtle Color
While Carolyn lived in neutrals, don’t be afraid to add just a whisper of soft colour. Muted sage, powder blue, or warm terracotta, as long as the shape stays simple.

It modernizes without distracting.

Casualize With Intent
One of the best ways to modernize Carolyn’s polished aesthetic is to contrast it intentionally.

Wear a silk slip dress with sneakers, or a tailored pair of trousers with a vintage band tee.

She might not have worn it herself, but she’d likely approve of the balance.

Modern Pieces with Carolyn Vibes: 90s Minimalism Reimagined

One of the reasons Carolyn’s style continues to resonate is that it wasn’t really trend-based to begin with.

That gives us freedom to reinterpret her look using contemporary pieces that honour her minimalist roots but feel right for the way we live and dress now.

Here’s how to channel her look with modern wardrobe choices:

1. The Updated Slip Dress

Then: A bias-cut, ankle-grazing silk slip in ivory or black
Now: Try brands like Silk Laundry, Cuyana, or Reformation for slips that offer more structure, adjustable straps, or unique back details. Look for modern cuts like square necklines, side slits, or midi lengths.
Styling Tip: Add a lightweight cardigan draped over your shoulders or wear it layered with a sheer blouse underneath for a fresh twist.

2. The Crisp Button-Down, Reimagined

Then: Oversized cotton shirts, often in white or pale blue
Now: Go for boxy cuts with dropped shoulders, slightly cropped hems, or shirts made in linen or TENCEL™ blends for a softer drape. Everlane, Toteme, and Arket make great options.
Modern Upgrade: Try it in a soft ivory or striped pattern for interest, or even a semi-sheer fabric layered over a bralette or tank.

3. Elevated Tank Tops & Baby Tees

Then: Ribbed tanks and short-sleeve tees in neutral colours
Now: Look for updated versions in organic cotton or silk blends with refined necklines. Leset, Skims, and The Line by K offer tanks and tees that feel luxurious but wearable.
Modern Twist: Tuck into a pair of tailored shorts or wide-leg trousers for that structured-meets-soft silhouette.

4. Tailored Wide-Leg Trousers

Then: Slim-cut trousers or straight-leg pants in suiting fabrics
Now: Relaxed, high-waisted wide-leg pants are a contemporary take on her look. Choose lightweight fabrics like linen, viscose, or breathable wool. The Frankie Shop, COS, or Aritzia’s Effortless Pant are go-to options.
Tip: Choose beige, cream, or soft charcoal to keep it timeless.

5. Minimalist Midi Skirts

Then: Bias-cut silk skirts or column-style cotton midi skirts
Now: Try Nanushka, St. Agni, or Vince for modern takes on the silk midi. Alternatively, cotton poplin or matte jersey skirts with clean lines give the same elegance.
Wear It With: A black tee and leather slides, or an oversized shirt knotted at the waist.

6. Simple Yet Polished Sandals

Then: Black leather strappy sandals, low-profile flats
Now: Look for fisherman sandals, refined toe-ring styles, or minimalist slides. Brands like ATP Atelier, Emme Parsons, or Aeyde make perfect modern versions.
Pro Tip: Stick to tan, chocolate, or black. Skip the gold hardware or embellishments.

7. The Modern Lightweight Blazer

Then: Neutral-toned suiting blazers worn over tanks or dresses
Now: Look for unstructured, oversized blazers in summer-weight fabrics like linen or viscose. The Row (if splurging), & Other Stories, or Uniqlo U make excellent options.
Modern Styling: Layer over a tube dress or pair with shorts and flats for contrast.

8. The Luxe-but-Easy Bag

You already know Carolyn loved a Prada shoulder bag, but today you can emulate the vibe with the following. They can be pricey but with some searching, patience, and luck you can often find them for much less.

• The Row’s Half Moon or Banana Bag
• Demellier’s Tokyo or New York Shoulder Bag
• A vintage 90s Gucci Jackie or Prada Re-Edition
• Celine Ava or A.P.C. Grace Bag for understated polish

Think sleek, small, no-frills, but made in a way that lasts.

9. Relaxed Silk or Linen Sets

This is where you can play. A silk short set, or linen tank and trouser set, gives a uniform feel that’s very Carolyn-coded, modern, intentional, and easy to wear head-to-toe.

Try: Posse, Deiji Studios, Skall Studio, or secondhand matching sets from Etsy or The RealReal.

10. The Everyday Sunglasses

Carolyn’s go-to sunglasses? Slim, slightly cat-eye or oval frames in tortoise or black.

Modern equivalents:

• Celine Triomphe
• Le Specs Outta Love
• Saint Laurent Lily
• Toteme Acetate Frames

Avoid oversized or mirrored styles; aim for timeless and structured.

Dressing for Today: Why This Aesthetic Still Resonates

In a world that often feels oversaturated with loud trends, there’s something undeniably grounding about returning to simplicity. Carolyn’s summer wardrobe feels especially modern right now.

Not because it’s trendy, but because it offers a kind of aesthetic relief.

Her looks remind us that fashion doesn’t have to shout. That being “put together” isn’t about overthinking or overspending. That personal style doesn’t need to be redefined every season.

When you dress like Carolyn, you give yourself permission to edit, to refine, and to focus, not just in your wardrobe, but in how you move through the world.