What Would Carolyn Bessette-Kennedy Wear To The Park?
Chill outfit formulas for a long weekend
Another day, another great content recommendation from a subscriber in this month’s Style Clinic. This time, it’s from Ina…
Thinking of what my style icon CBK would have worn to a playground? 😂
Genius! I could kiss you, Ina! What would CBK wear to the park? I have thoughts! She’s the undisputed Queen of classic basics, so her style lends itself to chill weekends and casual moments. Think comfy cardigans, crisp white t-shirts (destined to be ruined by sticky fingers in five seconds), relaxed denim, and flip-flops—the kind of pieces that make you feel elevated but cosy at the same time. Carolyn would have simply smashed playground style. Our Pinterest boards would be even more brimming with her outfit inspo.
So I’ve taken it into my own hands to come up with five looks here that I’d happily wear to the park with my little man during this end-of-summer season but also potter around in this Bank Holiday weekend. Are they perhaps a little dressier than what others might be wearing to the park? Sure. But if there’s one thing I’ve learned in my three years of motherhood, it’s that sometimes, putting the blinkers on can be a good thing. My worst year of dressing was when I was trying to ‘dress like a Mum’, which was a flawed concept in the first place because there is no such thing. Mums can dress however they please in a myriad of ways!! There is no box to fit into!!! It’s all about finding that balance between comfort, practically and ultimately, wearing whatever the hell it is that you want to wear.
A few general must-haves and guidelines:
All the shoes I’ve worn here are flats. That goes without saying for the park. I only really wear my trainers in the depths of winter, but I feel like Carolyn loved her classics and would have thrown on something like a Vans* or a Converse*. Building a shoe collection that’s largely flat and comfortable but slightly more elevated than trainers has been a BIG ‘a-ha!’ moment in my postpartum style journey.
I live my life on the edge. I wear white to the park sometimes!!! I do washing every day!! However, I keep it to the top half only, and I’ve tried to pick hardier options for the bottom half because if your little one is anything like mine, then the park is still very much a group activity.
We’re well and truly out of the ‘baby bag’ phase of needing to take a huge amount of stuff out with us, and being able to pack everyone’s bits into one of my own bags feels like we’ve turned a corner. If you still need something bigger, I’m very into this Glossier Tote* that’s structured so things don’t get lost and swim around in its depths. It feels very similar to the L.L.Bean Tote CBK wore.
And remember that not every trip out with your little ones will be a homage to CBK. I have once sat at the park in my pyjamas with a coat over the top at 7 am—it happens!
WHITE T-SHIRT + WIDE-LEG JEANS + FLIP-FLOPS + TOTE. Perhaps the most classically CBK outfit from the bunch. These jeans are new to me and really embody that relaxed but fitted balance, and are loose in the leg without being too wide (if you’re after a high-street dupe, then these look good*). I’ve sprinkled on a few accessories here, which Caroline wasn’t really a huge fan of, but for me it adds a bit of personality and polish.
OVERSIZED BLACK JUMPER + DENIM SHORTS + SUEDE LOAFERS + STRAW BAG. I feel like this look could work with either a large oversized jumper or something like a cashmere crew neck from the men’s department - that closer fit feels a little bit more CBK I think, but I liked the bigger silhouette here. The suede loafers might be a bit of a push for the park, but I’m thinking of a visit on a dry day when you can guarantee there won’t be any mud around. She wasn’t much of a shorts girl, so I’d imagine she’d do this with relaxed linen shorts or something longer.
NAVY CARDIGAN + BLACK LINEN TROUSERS + CHUNKY LEATHER SANDALS + ROPE BAG. I love this outfit. It’s like if CBK did a DONNI collab*. It feels very classic but very chilled at the same time. It’s worth noting that I swapped the bag around in these outfits for ‘variety’, but Carolyn was a sucker for outfit and accessory repeating. She’d grab the same tote day in, day out, so if I were staying true to my assignment, I would have paired the Glossier tote* with every single one of these outfits.
KNITTED BLACK TANK + STRAIGHT-LEG JEANS + FLIP-FLOPS + WOVEN LEATHER BAG. When I think of Carolyn’s style, I think of a great-fitting pair of straight-leg jeans in a vintage wash and a black boat-neck tank and flip-flops, and actually, it’s pretty playground-ready as it is. I don’t own a boat-neck tank, so I went for a knitted tank that feels a little more relaxed. I’ve done the DD bag but like I said, the Glossier Tote would probably be my go-to unless we were going on to something afterwards. Overall, this one feels like a classic that’s very easy to recreate. Sometimes, it’s best not to overthink it.
LINEN SHIRT + BLACK STRAIGHT-LEG JEANS + STRAP SANDALS + WOVEN LEATHER BAG. Carolyn LOVED a crisp white button-down, and if you search through the pap photos taken of her on the streets of New York, it comes up a lot. Although I would wear this outfit with a white shirt, I thought perhaps a more park-appropriate version was a beige linen shirt. A little looser, a little more relaxed, and less likely to get caked in bark chippings. The shoes are a stretch, but I’m thinking of a park trip paired with a nice lunch afterwards, or I’d do it with the flip-flops instead.
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Anna x
‘Mums can dress however they please’ PLS AND THANK YOU!
And I also have dogs and I hate my dog walking look!