17 Style Tips You Should Actually Learn from Carolyn Bessette Kennedy

Also enamored by the timeless style of Carolyn Bessette Kennedy? As a fan of her style and the way she approached fashion in general, I thought I’d break down some essential tips I’ve learned studying her outfits over the years.

Here’s the thing about me and the late CBK: we look nothing alike and while I enjoy her style, there’s actually very little about it I’d want to copy. However, like anyone with a passing interest in fashion, I’ve also been endlessly intrigued by everything she wore. To me she exemplifies that chic, fashionable woman of 1990s Manhattan. Like of course she worked for Calvin Klein and caught the eye of the hottest Kennedy.

It’s easy to look at her outfits and say, “What’s so special about anything she wears? People just want to copy her because she’s thin, blonde, and beautiful with jussttt enough imperfection to make her interesting instead of cookie cutter.” But there are countless beautiful, thin white woman who’ve passed through pop culture, and very few of them have had the longstanding intrigue around their street style quite like she has.

Below I’ll go into why that is as well as actual style tips we can all learn even if you have a completely opposite approach to dressing than she did!

Further Reading: I really enjoyed CBK: A Life in Fashion by Sunita Kumar Nair. She interviewed so many people in the fashion world who both knew or admired Carolyn, and it really gave such a great look into her style ethos. Also if you want books that evoke this world, read all of Beatriz William’s books! I don’t know how to describe it but start with The Secret Life of Violet Grant, and you’ll see what I mean.

The Style Advice You Should ACTUALLY Learn from Carolyn Bessette-Kennedy

1. Develop your own distinct style

Here’s the thing about Carolyn’s style — it’s very much authentic to her. You can tell she enjoyed fashion and crafted outfits both casual and formal that stayed true to her preferred aesthetic. Who knows if she inadvertently helped shaped 90s minimalist fashion trends or she followed them? Would she have been a trend hopper in the 2000s? We’ll never know; though I have a feeling probably not.

If you truly do not know where to start in developing your personal style, I highly recommend checking out KIBBE. It’ll help you figure out why your silhouette and features will work better with certain cuts and less so with others. Keep in mind, though, that this is just a way to get started. You don’t need to follow all rules and, at the end of the day, if you feel your prettiest and most confident in a neon green sack, wear it!!

To give you another example beyond CBK, check out the styles of Laufey and her twin sister Junia. They’re identical twins with similar but ultimately very different looks!

2. Establish a basic wardrobe foundation

The key to a basic wardrobe foundation is to have about 5-6 pieces per season you can wear without thinking. You’re so confident that they feel and look good, you could probably get dressed half asleep in the dark and show up to lunch looking just fine.

I can’t really tell you what you specifically should pick because it’s something you learn through trial and error and, of course is based on where you live. Carolyn worked in NYC which gets all four seasons and had her outside more often than other places.

If I had to guess for summer, I’d say her basics would be:

blocky sandal heels
fitted tees in black and white
a white button up (maybe in linen?)
a black silk slip
cropped jeans

In contrast, mine would be (linking to my IG posts!):

See? Both are very different!

3. Balance practicality and fashion

As mentioned a few times already, Carolyn was truly a symbol of 90s Manhattan! This means she was out and about town, taking the subway, walking between restaurants, working at Calvin Klein. Before she met JFK Jr., she was a normal woman with a normal (although in fashion, probably a slightly below normal) salary, living in a tiny apartment and spending most of her day out and about. She had a giant bag not for looks but utility — it had to fit everything she’d need for the day.

While most of us aren’t living quite that kind of life, there is an element of practicality that should go into our fashion choices. After all, most of us can’t live in flimsy silk dresses and dainty heels 24/7. We gotta function in society! I firmly believe that’s one of the reasons people want to copy her style so much. She’s clearly living in her looks. Even when she’s dressed for fancy affairs, you can totally tell which outfits she could go to an after party in happily and which ones she’s probably taking off as soon as she gets home.

4. Dress for the occasion

Speaking of, I think one of the cool things Carolyn has managed to do is to maintain her core style and dress properly for every occasion. Like even when she’s the most casual of outfits (sweatpants, sweater, and sneakers) there are choices there that make just as much a sense as when she wears a Yohji Yamamoto piece for fancier events.

Part of developing your style is making sure you have pieces that can fit for all aspects of your life and knowing how to approach anything from a black tie event to spending an afternoon at the park with friends.

5. Invest in items you’ll want to wear for as long as possible.

Think about the pieces of your wardrobe that you’d have forever if you could — purses, shoes, coats, special event dresses. Don’t be afraid to really research and invest in them.

While most people talk about Carolyn’s Prada purses and Hermes Birkin 40, you do not need to spend that kind of money, even though they are beautiful. In fact, if you do want to drop a few thousand on a purse, I’d recommend waiting at least six months before you buy. Make sure you’re not following a fad or getting caught up in marketing first!

Same with shoes. You don’t need Prada loafers or Hermes slides but you do want to invest in shoes that’ll hold up to your lifestyle. Apparently, a lot of the shoes Carolyn was photographed wearing are nearly impossible to find secondhand because they were the type of shoes women wore until they were so beat down not even a cobbler could save them. That’s the longevity you want!

6. Be picky and patient

Apparently one of the ways Carolyn and Lee Radzwill bonded was how they obsessed over bags and researched every little detail. I personally find things like that fun but I know not everyone wants to nitpick over stitching and hardware detail.

I do think it pays to be discerning and patient when picking out your clothes especially when it comes to finding quality items. We no longer live in a world where you can rely on brands or prices to indicate higher quality, so it probably takes more patience than it would have even in the 1990s.

Here’s some of my starter tips:

Look at fabric composition. I tend to go for as close to 100% natural fibers as possible but polyester has its time and place (mainly in swim wear and workout gear).
Try to see products in person before buying or make sure you can return if you order online. This way you can inspect its quality for yourself. Is the material thick enough? Are seams left undone? Does it actually sit like it’s supposed to?
Use secondhand shops!! Do you know how much secondhand cashmere goes in places like Poshmark and Depop? Way less than you’d think. Wool goes for even less!
Look up brand history discussion. A lot of brands tend to start off higher quality and then cheapen their production or materials as they get bigger or go public. For really popular brands, I like to check out forum discussions and only look at their offerings from earlier on.

7. Figure out a hairstyle that you can maintain.

From what I’ve seen and read, Carolyn had two distinct hairstyles and both were kind of iconic. Before she met JFK JR, she had darker hair, closer to her natural hair color. Apparently she’d wash it, stick it up in a bun, and then take it out when she got to work where it’d be that perfectly dry, tousled look. At some point when she got together with him, she changed to that iconic blonde color with seemingly perfect, glossy blowouts all the time. Considering the lifestyle and financial changes, it makes sense that she had a much more low maintenance style beforehand!

The key to both, though, is that her hair always worked for her and how she lived her life. Figuring out a hairstyle that does that for you just adds to what this whole post is about — personal style.

Personally, I tend to go for medium length hair with layers. If I have the funds and am in Korea, I get a digital perm for texture and waves. But otherwise I just blow it dry and curl myself. This style works for me the best because I’m overall pretty low maintenance and don’t always have my favorite tools on me when around the world!

8. Study the concept of contrasts

If you’re really struggling with figuring out what colors look good on you, go back and start simple — the idea of contrasts. Carolyn wore a ton of black. I’m sure her reasoning was partly practical and because it’s such a quick way to feel stylish and elegant especially in 1990s Manhattan.

However, part of why it works so well is because her fair skin and light blonde hair was such a sharp contrast to the color black whether she wore a simple T-shirt or structured jacket. Even if you go back up to the hair section and compare her old, darker hair with her lighter blonde hair against the black shirts, there’s a difference in the way the contrast works!

On the flip side, I have much darker coloring with dark hair and tan skin, so I actually hate wearing an all black outfit. It makes me feel like a storm cloud! I actually like all white dresses or white shirts.

Remember this is not a hard or fast rule but it’s just something to think of if you feel like nothing looks good. The same can be applied to colors. Experiment with wearing a contrasting shade!

9. Look for a tailor or learn how to alter your clothes.

Or befriend up and coming designers and then call them when you need help like Carolyn did!

Another reason much of what she wore looked so good was because it was quite literally tailored to her frame. Yes, even perfectly thin women in NYC benefit from a tailor. In her case, she apparently had a lot of friends in the industry who she could call up.

Obviously tailors can be expensive, so in the meantime just take a moment to learn to do light alterations to your own clothes. It’s actually very easy to hem a skirt or take in a waistline with very minimal sewing experience. Heck, sometimes tucking in a shirt or adding a belt makes all the difference.

10. Figure out your signature perfume.

This is more for you than it is for looks. When it comes to feeling stylish, I find it’s just as much about putting yourself on the mindset as it is wearing nice clothes and figuring out your hair. One of the fun ways to get into the mindset is perfume. Perfume is obviously an indulgence because no one needs a signature scent, but it’s still fun and can help you feel more stylish.

There’s a lot of discourse about Carolyn’s signature scent, which was Abdul Kareem Egyptian Musk Oil. Of course, what makes people want it even more is that it’s not produced anymore since I think the owner died? Not sure. Either way, you should not be trying to get a perfume just because they say someone you like wore it.

Start figuring out what scents you enjoy and go from there. Obviously, a fun way to do this is to go to your nearest beauty store and just start smelling different perfumes. I have quite the collection, so one day I’ll do post on them!

11. Create a capsule jewelry collection.

Jewelry, or the lack there of, is such a nice way to add just a little extra to your outfit. Obviously since minimalism was her thing, Carolyn was notable for almost never wearing it. And the few times she has, it’s been simple pieces and limited to one per outfit.

I think having a small capsule jewelry collection is such an good aid in personal style development. Just adapt it to what you like. If you love colorful earrings and maximalist styles, then go for that. If you hate the idea of wearing so much as a simple chain necklace and don’t actually want to own any jewelry, than that’s your capsule collection! Most of us fall somewhere in the middle. I personally have a pair of gold hoops and a gold heart necklace I wear with pretty much every outfit whether it’s hiking or at a wedding.

12. Never underestimate black and white clothing.

At the end of the day, never underestimate the beauty of black and white clothes. They’re good, solid basics for a reason. When in doubt, putting on a black skirt or pair of pants and a nice white top will result in a clean, classic outfit no matter what.

13. But do NOT be afraid of patterns and color

That said, not even Carolyn Bessette Kennedy wore only black, white, and denim! There are quite a few photographs of her experimenting with prints and colors like above. Don’t feel like you have to stick to neutrals and monochrome to be stylish. Experiment, try things on, and have fun with it!!

14. Logos cheapen everything.

A good thing to note, and something I’ve always agreed with — logos make everything feel cheaper. Yes, even that fancy Louis Vuitton luggage that costs an arm and a leg or those Hermes bags with the giant perforated H look cheap to me. If you disagree, that’s fine! Enjoy your logos!

But, yes, I personally find logos very cheap looking. I don’t even like when bags have metal clasps or medallions that are too big. For example. I actually love the look of the Dior saddlebag but I’d want that giant D taken off.

15. Look for accessories that suit you

Do I think Carolyn’s Selima Optique Aldo sunglasses look gorgeous on her? Yes. Do I also know that those sunglasses would look absolutely ludicrous on my face? Also, yes!!!

When you look for accessories, make sure to look for ones that suit your face and not just something you want to try and copy from someone like Carolyn. My face is wide and my head is definitely bigger than hers, so those sunglasses who look like goggles on me. Honestly, I’ve bought the same $9.99 sunglasses from Amazon for almost a decade now and before that it was a similar looking pair on G-Market in Korea. I’ve played around with other styles but those sunnies are still what works best and they last as long as I don’t squish them or accidentally sit on them.

(And, yes, I hate that I can only find them on Amazon which is why I do my best to keep them nice for as long as possible so I don’t have to give Bezos any more money than necessary.)

16. Wear clothes over and over and over again.

Make like Lizzie McGuire, and be an outfit repeater! If you invest in pieces you love, wear them over and over and over again. Get creative and see how you can style the same piece in different ways for different occasions. We really don’t have that many photographs of Carolyn’s style over the few years she was in the public eye, and even then we can see her rewear different pieces in different ways. See the Yohji Yamamoto jacket above.

17. Remember that no amount of style can replace an interesting and friendly personality.

If you read anything from people who knew and loved Carolyn Bessette Kennedy, they all have warm things to say about her. In fact, many of her close circle have rarely spoken about her, preferring to maintain the privacy she so desperately wanted towards the end of her life. What struck me reading their accounts was that she was an intensely warm and friendly person to those around her.

Now, you can be cynical and say, “Well, obviously — no one is going to speak ill of the dead.” Which, fair. But, I don’t know, I think if she’d been a truly vile person or nasty jerk, the accounts of her would be much more neutral. There also wouldn’t be so many specific stories of her being generous or funny!!

That’s all to say that personal style isn’t just something you see or smell or touch. It goes right down to your personality and how you carry yourself beyond your clothes, make-up, and hair color. From the sounds of it, that effortless cool Carolyn seemed to have in her physical style started much deeper than what clothes she picked out for that day. So before you obsess over her exact headband or perfume or which Birkin bag she carried, take lessons from how she interacted with those around her and what legacy she left as a human being first.

And there you have it — the style tips you should ACTUALLY learn from Carolyn Bessette Kennedy. Any to add? Let me know!

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