I Can’t Believe How Much I Fit in A Carry-On

From the archives, Updated May 2022.

I consider myself a pretty efficient packer. After years of mastering the carry on, it just keeps getting easier. I stick to a color story that can be mixed and matched numerous ways. After deciding on the palette, I look at activities and events I’ll be attending and make sure I have pieces that are comfortable and appropriate. I further edit and select pieces that are what I call travel worthy – meaning they can be rolled or squished and then hung to release wrinkles.

On my most recent trip for four nights in New York, I packed hastily at the last minute and tossed in way too much. I have outfits here that could take me through a couple of weeks at the very least. Amazingly, I even surprised myself that everything fit in my carry-on. It’s sort of ridiculous. I brought six pairs of shoes! Three belts. Three handbags. Black and white pants – then black and white tops – both short-sleeved and long. Four pair of jeans…white, black, blue and ecru. A hat, two scarves and an umbrella. Oh, I almost forgot the two dresses and a skirt.

The top photo shows what I wore on the plane…clearly comfort driven. The tote is the must to making all this magic work. All my toiletries go here. I have a make-up bag, a clear liquid TSA bag and then all other dry toiletries in another pouch. I placed my black Chanel bag at the bottom, flat, and my Tod’s bag (similar) in its dust cloth cover in the tote. The jewelry I brought in little pouches were stuffed in a Tod’s bag. An umbrella, iPad, chargers, and headphones also go in the tote. There’s enough room if I get too hot to roll my Moncler jacket and fit it in too.

My day time outfits centered around the option of either jeans or a dress. All could be worn with my three most comfortable walking shoes for this trip…a rotation between two sneakers and a thick soled sandal. A tee shirt with jeans carried me from SoHo to Williamsburg – walking there and back in my Puma sneakers and J. Crew hat. For an afternoon at The Met, I wore all white with my trusty black Marni sandals. On another day walking around, I tossed on a sleeveless Helmut Lang striped shirt with ecru frayed jeans and the hat. I wore a simple white shift dress with black sneakers for a day of shopping stores.

When I wanted to look more pulled together for lunch, dinner or an event, I had loads of options. I didn’t even have the chance to wear all the pieces I brought but I liked the idea of variety. I wore a Tibi blue cotton dress with Chloe beige sandals for dinner one night. For brunch, I decided on a Helmut Lang navy crinkled skirt and polo. Another dinner I put together a black sheer top with white pants and flat studded Miu Miu’s. For an event one morning, I wore all black – cropped flares and a tie sleeve top – again with the black flats. I never wore the heels.

The key is the versatility of each piece. I could easily have put any of the tops with any of the bottoms and been fine. Sticking to a tight palette is also essential. This particular trip, like many, I focused on black, white and navy. The added pop of pink goes with any of it. I brought one necklace, matte aquamarine layered beads from Diane Cotton that added just enough flair to any outfit I wore.

Oh, I almost forgot. I bought a pair of shoes and a skirt that fit in the suitcase for the flight home.

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