If you’re scrolling through Instagram right now, you’ve probably noticed the endless rules for looking “chic.” Belt this, brooch that, drape your sweater over your shoulders just so, layer three necklaces, tuck your tee in a precise way… the list goes on.
And then there’s Carolyn Bessette-Kennedy. Based on what I’ve seen on Love Story and the photos I’ve seen of her online, it looks like she didn’t complicate things. Jeans. Tee. Done. Long sleeve or short sleeve, tank or button-up, paired with a pair of jeans and maybe one accessory - she made it look effortless. No logos, no overthinking, no rules. She didn’t need a stylist or a TikTok tutorial. She just wore the clothes, and the clothes served her, not the other way around.
Each outfit feels effortless and simple, but somehow still visually compelling. Why? I think the reason is proportion and contrast.
Sometimes it was baggy jeans with a relaxed tee. Other times tailored denim with a fitted button-up. And sometimes one relaxed piece paired with one more structured one.
Baggy with baggy somehow feels intentional.
Tailored with tailored somehow feels easy.
How does she achieve that?
The awareness of proportion and contrast is what makes basics feel intentional and interesting instead of boring.
And I think that’s the point that often gets lost.
The myth is that you need more to look chic. More accessories. More styling. More layers.
But when the foundation is strong, basics are enough.
So let’s look a little closer.
Outfit Analysis
I started with gathering images of CBK in jeans and a tee and asked myself why each one works.
The top left photo is probably my favorite. Loose fitting denim, a loose long sleeve black tee, and black flip flops. On their own, those pieces are incredibly casual. Comfortable. Chill. Then she finished the look with a structured black bag, chic sunglasses, and hair pulled back in what looks like a bun.
That contrast is why it works.
The clothing feels relaxed. The accessories feel refined. Together it looks effortless, but not accidental.
Let’s look at one more - bottom left with the dog. She’s wearing cropped denim that’s fitted but not tight, and a black tank that skims the body the same way. Both pieces are simple. But paired with heeled sandals, the whole outfit shifts. It’s still minimal, still understated - just slightly elevated.
She really used her shoes as tools. Flat sandals kept things easy. Block heels sharpened denim. Loafers grounded dresses. The clothes didn’t change much - but the tone did.
Looking At My Closet
I’ve been thinking about this and how it relates to my own closet and my own approach to getting dressed. And I think my key takeaway is the importance of having (or investing in) really good basics in different proportions to fit what you need on that day makes getting dressed easy.
Denim
With denim, it’s really personal. There aren’t any hard and fast rules about which style denim you have to wear - the most important thing is that you feel good in them. So if you don’t like these styles, skip them and wear what you like! I’ve found 5 pairs that mirror the looks in the photos of CBK above - with different hemlines, different washes, and different fits. It seems like she tended toward the classic look of straight leg, mid-rise, looser fitting denim. One thing I love about having different hemlines is the way you can then be flexible about different footwear.
Tees/Tanks
If jeans and a tee are enough, then the tee matters. When deciding what to buy consider a few things: neckline/ strap thickness (for tanks), length of the shirt (is it cropped, does it need to be tucked in, will you wear it tucked out), fit (do you want it tight, or maybe size up if you want a relaxed fit), and for tanks.
I like having (all in white and/or black):
a tee that isn’t cropped but doesn’t have to be tucked in (both long and short sleeved)
a tee that can be tucked in or left out (both long and short sleeved)
Button Ups & Sweatshirts
Ok these are more relaxed fitting long sleeve tees and really lightweight sweatshirts, which I think speak for themselves. As I mentioned earlier, paired with more refined accessories, these can look incredibly chic and put together too.
As for button ups, it’s great to have a few go-tos in your toolbox. It’s great to have one that can be dressed up and more refined, maybe a little more structured, great for tucking in. And one that feels relaxed and casual and a little oversized. Start with white, black, and I love a pin stripe as your foundations…you can then add color or pattern later once you have your basics.
Shoes
Last, but not least, the shoes. In my perusing of CBK, a good black flip flop, a block heeled sandal, and black loafers were part of her regular spring/summer rotation. All classic styles. She’d wear loafers with a slip dress and the block heels with jeans. She really used shoes as tools to keep her outfits feeling easy, classic, and at the same time, elevated. I’d swap the loafers for clogs (or these) or these Mary Janes (also classic styles), but the other 4 pairs I’ve linked are chef’s kiss in my opinion!
One last thing…if you’re searching for the perfect CBK inspired sunnies, I came across these, and they look really good!
xo, Abby