Buy What You Like, Not What Carolyn Bessette Kennedy Liked
I was going to title this post something else entirely. Something along the lines of: “So long as you’re copying Carolyn Bessette Kennedy’s style, you will never be chic yourself.” But aside from it sounding a bit too harsh, I noticed that many have started covering that same subject on Substack, so I’ve decided to pivot.
CBK is the perfect example of “you can’t buy taste.” You can buy her turtleneck, a beige skirt, and a Prada bag, and yet you will never look like her. It’s because she didn’t read a “10 best black tops” article and purchase the most appealing option. She also certainly didn’t Google “How to Dress Like Cindy Crawford” and try to copy her exact outfit. She probably went into various fitting rooms, trying on a range of seemingly similar-looking black tops before finding the one with the right stitch, length, material, and drape that best suited her specific body.
She wasn’t buying what others wore; she was buying what she liked on herself. That is a person who is very secure and comfortable in her own skin, and you should be too.
I understand the need for PR reps to email me a list of tops and bottoms, conveniently picked out from the brands they represent, to best emulate Carolyn Bessette Kennedy’s look. But it’s fruitless labor. If you want to copy Carolyn, you have to forget about what she’s wearing. You have to get really good at knowing your own personal style and wear it with the same comfort and confidence she did.
I love Carolyn’s style. I, much like everyone else, am drawn to her effortless presence and restrained styling. But it’s a “look, don’t touch” kind of appreciation. I’m not a white woman, I don’t have beach-blond hair, or an impressively unimpressed expression on at all times. Where she might pick loose-fitting white T’s, I look better in form-fitting ones. Where her legs are made for straight-leg jeans, I can rock baggy boyfriend jeans like no one else. And how did I learn that? By going from store to store, trying on jeans from the men’s department as a young teen, before finding the one with the right fit for me.
We’re all a little too easily influenced nowadays. It’s kind of hard to avoid, what with the Substacks and the Instagrams and TikToks and whatnot. But what is your mission here? To jump from one trending woman to the next and adopt their styles each time? Wouldn’t you rather create your own IT factor? It’ll make getting dressed in the morning a whole lot less confusing every time.
I recently wrote an article about going back to in-person shopping. After half a decade as a shopping writer, I lost touch with what excited me. I covered trends and picked out pieces that would resonate with the masses, rather than niche finds for unique tastes. I clicked those links that the PR reps sent me and included them in articles for everyone else to enjoy. I said yes to free clothes, not because they were the best for my body, but because they were free… and with time, my personal style started to get watered down.
Fashion should always start with you. Trust in your internal compass, the one that points you toward a specific shirt that’s hanging in the store. Have a dress-up party and see which pieces in the reflection excite you the most. Don’t buy anything that doesn’t give you that jolt of “YES”, because even if you need a new crewneck sweater, not all are made the same. Wait until you find the one with the exact neckline, fabric, length, weight, and color that best represents you. In short, buy what you like, not what looks good on others.
