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Carolyn Bessette Kennedy: How to Style 5 Timeless Pieces for a Modern Edge

Thursday, April 09, 2026

The Fashioneaseta/Carolyn Bessette Kennedy: How to Style 5 Timeless Pieces for a Modern Edge
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The recent success of FX's Love Story: John F. Kennedy Jr. and Carolyn Bessette has brought Carolyn Bessette Kennedy ("CBK") and her timeless style back into the forefront of fashion after nearly 30 years, and for good reason. Her effortless elegance created through a wardrobe of classic pieces in a neutral color palette resulted in a style that was both understated and impactful.

What draws me to CBK's style? We have a similar design aesthetic. I like clean, simple lines. And even though I generally go bold when I wear color, I love to wear neutrals as well. In Love Story, one of Carolyn's signature colors is my all-time favorite neutral - black.

Her style philosophy was straightforward: quality pieces with an impeccable fit. She understood neutrals, invested in classics, and kept it simple. The pieces she wore were very versatile. Depending on how she styled them and what she wore them with, they would suit a number of different situations. I believe that today's women are looking for pieces they can wear for a variety of occasions and that give them more bang for their buck.

Although I love color, I believe that neutrals form the basis of any wardrobe. Wearing neutrals is the easiest way to dress when it comes to mixing and matching items in your closet. Color analysis becomes important because each individual's best neutrals will depend on their color season. Black is not flattering on everyone. And for those that like to wear gray, brown, and tan, the undertone and depth make a difference.

​In this month's blog post, I've chosen five items from CBK's wardrobe in Love Story for your consideration as wardrobe "essentials". Note that this list doesn't include some of the items that were her signature, such as a pencil skirt and fitted turtleneck sweater, because I wanted to focus on items that work for women of all shapes and sizes. You may already have some or all of these items in your closet. My goal is to give you different ideas on how to style these wardrobe "essentials" to showcase your own individual style.

1. The Silk Slip Dress

How CBK Styled It:
​In Love Story, CBK typically wears slip dresses alone without any layers. The simplicity was part of the appeal—minimal accessories, understated shoes, and an effortless elegance that made the dress the focal point.

How to Style It in 2026:
As a classic, versatile piece, how you wear it really depends on the occasion. For a more casual look, layer a denim jacket over it with either sneakers or flip flops. Wear it with a slouchy cardigan and boots or flats for a more elevated yet still casual look. Consider heels and a pashmina or a structured blazer for a more formal look.

One very popular way that I remember wearing it in the 90s was with a fitted tee layered underneath. I actually think that's still a very fresh (and practical) way to wear it today!

Neutrals by Season
Universal: Navy
Winter, Bright Spring, and Dark Autumn: Black
Autumn: Champagne and Soft Brown
Summer: Gray, Taupe
Spring: Ivory and Camel​

Recommended Investment Piece:

Washable Silk Slip Dress - Long

Washable Silk Slip Dress - Short

2. The White Button-Down Shirt

How CBK Styled It:
​​In Love Story, you see CBK wearing a white button-down to work paired with a black pencil skirt or trousers. The sleeves are usually rolled or pushed up and the neckline is open for a more relaxed look.

How to Style It in 2026:
A button-down shirt inherently has a formalness about it. In 2026, I love to find ways to make a button-down look more casual and relaxed, whether that means pairing it with jeans or a pair of shorts or wearing it open over a tank, camisole, T-shirt, or bathing suit. You're only limited by your imagination!

My favorite way to wear a white button-down is with jeans and a vest layered over it (whether a menswear-inspired vest or a cropped cashmere sweater vest). I also like to swap out jeans for a colorful trouser. As a Bright Spring, two of my favorites are a bright red or kelly green pant.

The Bright White Problem:
Bright white is not flattering on everyone; it generally looks best on Winters and Bright Springs. If bright white is not in your color palette but you still love the crispness of a bright white button-down, consider wearing it with statement accessories (either a scarf or jewelry) or under a layering piece in a color from your season. If you plan to wear makeup, wearing makeup in your color season will also help. Another option is to find a "white" button-down in a shade that works for you and your season.

Neutrals by Season
Universal: Ivory
Summer: Soft white (hint of gray)
Winter and Bright Spring: Bright white

Recommended Investment Pieces:

100% Organic Cotton Poplin Long Sleeve Shirt in Classic White

Organic Cotton Poplin Classic Shirt in New Off White

3. Black Trousers

How CBK Styled It:
Working for Calvin Klein, who was known for his minimalist aesthetic, black bottoms, whether pants or a skirt, were a staple of CBK's wardrobe in Love Story. She has a pair of kick crop trousers that she wears in Episode 1 with a black turtleneck for a monochromatic look. In a later episode, she wears a pair of black wide-leg trousers with a white button-down shirt.​

How to Style It in 2026:
Don't just look at black trousers as part of your work wardrobe. They can easily be dressed up or down based on the top, layering piece, shoes, and accessories you wear them with. Wear with a T-shirt, denim jacket, and sneakers for a more casual look. To completely change the vibe of the outfit, wear the same T-shirt and pants with a moto jacket and boots. And to change the vibe a third time, try a structured blazer and heels with the same tee and pants. The key is to find a black trouser in a flattering silhouette. One of the most popular styles right now is the wide-leg pant. While a wide-leg pant is flattering on a lot of people, pay careful attention to how wide the leg is. Too wide of a leg can be overwhelming on petite frames especially.

I personally like to wear black trousers for more special occasions, usually with a blouse, cashmere sweater, or silk or satin shell.

Why Everyone Should Own Dark Trousers
Your color season matters primarily for the colors that you wear close to the face. Everyone should own a pair of dark trousers, and here's why:

Practicality: A dark trouser is practical and doesn't show dirt the way a light-colored pair of pants does. I remember wearing a white pair of shorts in Madrid only to wonder why they looked sooty by the end of the day.

The slimming effect: There's truth to the saying that "Black is slimming." In general, dark colors absorb the light while light colors reflect light. When light is absorbed rather than reflected, a surface automatically looks smaller. If you're looking to minimize a particular feature or make it look smoother, wearing a darker color in a matte fabric is the way to go.

Versatility: Can be easily dressed up or down.

If you don't like to wear black: Navy, charcoal, chocolate brown, wine, burgundy, and dark green are other good options.

Recommended Investment Piece:

The width of the pant leg is just right and the pleats are slimming for anyone who is concerned with their mid-section. Available in black and a wide variety of colors and patterns.

4. The White T-Shirt

How CBK Styled It:
In Love Story, she wore a fitted crewneck T-shirt to work under a black jacket and jeans for a relaxed yet polished look.

How to Style It in 2026:
Styling a white T-shirt deserves its own blog post. Literally, you can style it however you'd like for whatever occasion you like. The key is to find the right neckline and fit that best suits you and the occasion. The fitted crewneck tee from Love Story is not going to be the most flattering cut on everyone if you plan to wear it alone. A crewneck tee that's roomier through the body with sleeves that aren't fitted to the arm is generally a safe bet.

Personally, I love bold accessories with a white T-shirt, such as a colorful scarf or statement necklace. Wearing these types of accessories in your color season can soften the look of a bright white T-shirt if bright white isn't one of your most flattering colors.

I have many variations of the white T-shirt. While I'm partial to the crewneck tee, I also own white T-shirts with different necklines, such as V-neck and scoop neck, and in different lengths and fits with different sleeve types (flutter, cap, etc.). I wear them layered under sweaters and cardigans when it's cold. When it's warmer, a white T-shirt and jeans is one of my favorite looks. I change it up with accessories and shoes.

Neutrals by Season
The same principles apply to choosing the right shade of white that we applied to a white button-down shirt. T-shirts labeled as "Ivory," "Ecru," or "Natural," are good options for anyone who wants an alternative to the bright white tee.

Recommended Investment Pieces (all under $20):


Organic Cotton Micro-Rib Crewneck Tee (Quince) - Soft White; Size up if you want the fit to skim the body.
EveryWear Crew-Neck T-Shirt (Old Navy) - Calla Lily (White)

5. The Crewneck Sweater (in Cashmere or Wool)

How CBK Styled It:
In Love Story, she wore a crewneck sweater (likely cashmere) to work with a black skirt, sheer black tights, and knee-high black boots for a polished, professional look.

How to Style It in 2026:
Similar to a white T-shirt, you can literally style a cashmere crewneck sweater for any occasion. For a modern, relaxed yet dressy look, I love pairing a slightly oversized crewneck sweater with a satin skirt. For another elevated casual look, consider wearing the same sweater over a button-down and jeans with your favorite pair of sneakers.

I personally love a crewneck cashmere sweater. I have several, but my favorite is a black one from Quince that I wear on repeat through the Winter and also wear in the Fall and Spring because it's lightweight but warm. I tend to wear it layered over a fitted T-shirt with jeans, colored denim, cords, or chinos for an elevated casual look. For footwear, I'll wear either short boots, loafers, or sneakers.

Neutrals by Season
Universal: True Navy
Winter: Black
Autumn: Charcoal, Teak
Spring: Ivory
Summer: Heather Gray, Brown

Recommended Investment Piece:

My current favorite is Quince's Mongolian Cashmere crewneck sweater, which probably manages to find its way into many of my blog posts due to it being such a workhorse in my wardrobe (and very reasonably priced for the quality!). Note that the colors noted above relate to this sweater's available colors.​

Building Your CBK-Inspired Wardrobe

The CBK Approach:
Quality, versatile pieces
Neutral color palette
Impeccable fit
Simple and intentional styling

The way that CBK wore these items resulted in a lux and elevated look. However, I believe these five items are so versatile that they can be styled in a way to reflect your personal style, whatever that may be.

The Key to Making This Style Work for YOU:
Understanding your most flattering neutrals reduces decision fatigue by providing the "wow" shades that will work best to build your wardrobe. Start by choosing up to three neutrals as a foundation for a minimalist wardrobe. Navy blue, ivory, and burgundy are three neutrals that tend to look flattering on a wide range of people. But picking your color palette of preferred neutrals is only the first step. The next step is finding pieces that fit properly and are in the right silhouettes to suit your personal style.

Ready to Start Building Your Capsule Wardrobe?
If you're interested in discovering which neutrals suit you best, a color analysis session will give you clarity on your perfect neutral color palette. If you'd like to create a capsule wardrobe that includes some or all of the five items above, I'd recommend a wardrobe consult where we'd start by shopping your closet before I assist with filling any wardrobe gaps and providing suggestions on how to pair items together. And remember, just because an item may be considered "classic" doesn't mean that it can't be worn in unique and unexpected ways. Let me help you make these five timeless pieces your own.

📧 info@thefashioneaseta.com 📍 Richmond, VA & Central Virginia and beyond

Let's build a wardrobe that works as hard as you do.

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Hi, I'm Roxanne!

Style Educator
12 Season Color Analyst
​Fashion Efficiency Expert

My goal with The Fashioneaseta is to make it as easy as possible for busy women to look put together so that they look and feel their best while saving time and money in the process. Let me help you create a wardrobe that you love of stylish, comfortable, multi-functional pieces that are a true reflection of you.

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