It’s A Vibe: CBK on Vacay!

An analysis of all of Carolyn Bessette Kennedy’s best summertime looks!

Hello everyone!

I am a long time admirer of Carolyn Bessette Kennedy and her chic 90s style. In the last few years, I’ve always looked up to her minimalistic style and attempted to emulate it in my own way. I usually do so during the winter and fall, since much of my favorite photographs are featuring her wearing classic blazers, midi a-line skirts, Prada coats, and dreamy boots. However, this summer, I’ve also been taken with her summertime style and how she would dress when she was on vacation. So, I thought I would do a little CBK study for you all, because I think it would be so easy to thrift pieces similar to hers!

I sourced these photos from some of my favorite CBK accounts on Instagram, and you can follow them here: @carolyn_iconic, @carolynjeannebessette, @carolynmystique, @carolynbessette, @allforcarolyn, @cbk_closet, and @jfkjrpage since they post about John and often feature Carolyn as well. Yes, I do follow each and every one of these. Yes, I am aware I am obsessed.

Her beachside style surprised me actually, since almost every picture I looked at while I was researching this post features Carolyn wearing longs sleeves, a sweater, or a jacket. I know that if you’re boating or out on a windy beach you’re going to want to bundle up to ward against the chill, but it still made me think about how Carolyn must have viewed her clothes, at least in part. These outfits are all very practical and stylish at the same time. They serve their purpose but they’re still chic. It might just be because it’s Carolyn wearing them, and even her essence was pure style, but I digress.

I had an extremely difficult time picking which photo I liked the best of all Caolyn’s looks, so excuse the extreme amount of pictures in this post! But I think what might work best is if I react to each collage of pictures in order, and explain why I think they’re special. I’ll be going in a clockwise order:

This first photo of Carolyn and John dancing is a gem, not just as a study of her fashion sense, but I just love the clothes all the other women in this picture are wearing as well. And also… JFK Jr. in Birkenstocks?? A classic. But what I like the most about Carolyn’s ensemble here is 1) the daring white-on-white, and 2) pop of color with her red loafers. She’s wearing a simple tank top, linen or khaki pants with a tailored fit. The simplicity of the outfit is what I think I like the most. Because you can tell she wore her hair down, and it draws attention to how naturally striking she really was. My only question… Loafers to dance in?? I feel like I would get some pretty nasty blisters. But these types of pieces are pretty easy to thrift, I feel like I see loafers in this style every time I go to Goodwill!

This picture of Carolyn up next is her with John and some family/friends on a boat. You don’t see her in shorts or skirts this often, so you can see her long legs. She’s also wearing a long sleeve shirt or sweatshirt with a possible raw hem (since it looks a little rolled to me), and her hair is down again. Her shorts seem to be cuffed as well. To me, this speaks to Carolyn’s attention to detail. It’s the little things like this that make an outfit interesting or exciting. A rolled cuff, a raw hem, and a shock of leg.

Carolyn in a plain white long sleeve button down and a pair of jeans. Not buttoned up all the way, ofc. Gotta stay casual! Pair it with a loafer or a sandal, a small pair of sunglasses, and you’ve got yourself a look. I also like how her hair is tied back. Very casual, but you can still tell there was thought behind this!

I wanted to feature this picture of Carolyn and John together, because I like how casual they are here in this photo. John in a billowy button down, Carolyn in a blue polo shirt. They look relaxed, and I’ve always liked that about them both. And again, polos are SO EASY to thrift, and if they’re styled well they look super cute and casual. For example, pair it tucked into a denim skirt with your favorite pair of sneakers, and you’ve got yourself a cute summer look. I have two for sale on my vintage page @thegingerthrift, just sayin’ ;P

I have been so into wearing hair scarves this year, and I love this photo of Carolyn wearing one. I’m not 100% sure if this is even taken in the summertime, but it’s still a vibe. I like how she’s wearing her iconic sunglasses as well. According to @cbk_closet, I’m pretty sure they’re Selima Optique “Aldo” glasses. You see Carolyn wearing either these or similar in many of these photos. If you’re on the hunt for a similar pair, this style is pretty popular at the moment and you can find them all over. But, as always, I prefer to thrift, and I got a similar tortoiseshell pair at Goodwill!

I’m wearing the scarf differently than Carolyn it, but I like to think it’s a similar idea! They’re one of my all time thrift finds since I get so much wear out of these sunglasses. They’re Ann Taylor, which isn’t as ritzy as Carolyn’s, but I adore them and wear them every day!

This first photo is another example of Carolyn in a white button down and Levi’s (I think?). She’s also walking barefoot on a pier. The epitome of casual summertime goodness! Since this look is so similar to the other I won’t say much, other than the fact that I love how comfortable she looks here. Hair down, staying cool in her billowy shirt, and well-fitting jeans.

The next row of pictures are all featuring Carolyn wearing one of my favorite pieces from this post– A bright yellow rain jacket! I think she wore this often while boating, and this makes a whole lot of sense, so she didn’t get too drenched from the spray. But I like the examples of what she wore it with. A black turtleneck, a backwards baseball cap, a plain white tee (layered or no), brown khakis (paired with black! Another small rule breaking moment). All choices that made this quintessential and practical piece a little more interesting.

Continuing clockwise, the next two photos show Carolyn wearing a light blue turtleneck and khakis, barefoot again. I have no evidence to back this up, but I have a sneaking suspicion the turtleneck could be cashmere as well? This is just such a laid back look, and I love how cozy she seems on the blustery beach.

This last picture is another one showing Carolyn all bundled up, and is one of my absolute favorites because of how candid it seems. She’s wearing leggings and a baggy sweatshirt, which looks to be long enough to reach her mid-thigh (at least!). It’s obviously chilly on the beach, with John covering himself with his jacket like a blanket and the little kiddo with his hood up. She just looks so comfortable and at peace here.

Another accessory you often see Carolyn with in her vacation pictures is this L.L. Bean canvas tote bag with navy blue detailing. It’s super preppy, but also the quintessential beach bag. These pictures inspired me to look into getting my own, but since new ones are around $40-ish dollars, depending on the size you want. Instead of shelling out that sort of money, I decided to investigate my secondhand options. So I went onto Depop, and you would never guess what I found! A vintage L.L. Bean tote bag, the same large size as Carolyn’s, but with a more interesting touch…

It’s green and navy blue, and it has my exact initials embroidered on it! When I tell you I was so shocked to find this for sale, I mean it. And I got it for a true steal… right around $15. And even though due to Covid it seems I may not be able to get to the beach this year, I’ve still used this tote nearly every day since I’ve gotten it. It holds my laptop perfectly, and other things like my planner, Kindle, bucket hat, and the like. I even take it when I’m out photo-shooting, to house my change of clothes if I’m making a day of it.

The last set of photos! Even though there are still PLENTY more outfits I could have rambled on about, there does need to be an end to this post at some point… Going clockwise again, here is this photo of Carolyn eating at a restaurant with a friend in New York. While this isn’t her on vacay, I thought it still had super cute summer vibes. Again, she’s got a simple outfit together, with a black tank top, linen or khaki pants that seem to be either capris or an ankle length, and Adidas sneakers. I also think I see her wearing a black belt, with the tank tucked in. So if I had to guess, the pants were probably tailored as well, maybe even with a pleated pant leg. My imagination is running wild here, but I digress. This is what I love the most about each of Carolyn’s outfits. No matter their simplicity, she always throws in interesting details to spice it up, like a belt, a pleated pant, or a fun sneaker. And in the next photo she’s wearing a similar outfit as well, only with a spaghetti strap tank.

I love this next photo, because Carolyn’s hair is dazzling! She looks as if she’s been out on the beach all day, and is back home to cook dinner. She’s wearing a black tank yet again, but I also spy a green patterned skirt. We can’t see the full ‘fit, sadly, but I like to think it’s a midi-length wrap skirt with a Hawaiian floral pattern. Who knows, maybe the black tank could actually be her swimsuit? Add a cute wedge sandal and you’ve got all the summery, beachy vibes!

Finally, this last picture shows Carolyn out to dinner with her friends! She’s wearing a gray-silver slip dress with lace detail on the neckline. According to @cbk_closet on Instagram, this picture was taken at a restaurant called Indochine in NYC, and the dress was from Calvin Klein. (See the Instagram post below!) I adore this picture because it shows Carolyn supposedly mid-laugh, and I just love to imagine what she must have looked like sitting with her friends telling stories, swishing her pretty long blonde hair from shoulder to shoulder as she sips her wine. I picture her wearing this dress with a pair of strappy sandals or a kitten heel, and a teeny baguette bag.


Which one of these Carolyn looks was your favorite? For me, I saved the best for last… That slip dress takes the cake, IMHO! I loved putting this post together, so much so I think I may make this a series! Not just with CBK, though i do think I want to make another one of these for the fall/winter, but for some of my other favorite style icons too! Who would you like to see next? Let me know in the comments below, or connect with me over on my Instagram @thegingerintrovert, I would love to chat!

Until next time!