How to Pack Outfits You Actually Wear On Vacation
The advice I used to style lawyer & ah.mi founder Rachel Johnson for her trip
The first time I packed for a big vacation, I brought my entire closet. I was 19-years-old and visiting my best friend Caitlin in Paris. I’d never been to Europe before, and since I wasn’t sure what to wear, I figured I’d take everything I owned. Mostly Forever 21, J.Crew from the clearance store in Lynchburg, Virginia, and a couple of things I bought specifically for the trip.
I landed at Charles de Gaulle with two checked bags, both the size of a small child. Caitlin helped me lug them up and down the Metro stairs, never once saying something about my excessive packing. Of course I only wore a fraction of what I brought, instead opting for one of the many striped things that I found at a random boutique in an attempt to look like a French girl. Years later, I’d look back and cringe at what I put my friend through, but it made for a funny story.
Now when I pack for vacation, there are a few things I think about to make sure I feel good getting dressed, without having to check a bag. I hopped on Zoom with my friend,
, the co-founder of J&O Law and founder of , last month to help her do the same for her upcoming trip to Anguilla. Use this advice for your next vacation, or hire me to style you. It’s a better investment than panic-buying things you’ll never wear again ;)Note whether there are any events or activities you want to dress for
I like to start here because it helps me figure out what role I want my clothes to play on vacation. Supporting? Background? Packing for Savannah with my friend
was different than packing for my family’s annual trip to Ocracoke Island because Rosalee and I had occasions we wanted to dress for, pretty floral things we don’t wear as much in New York, and at Ocracoke, I just wanted to feel beachy and relaxed.Rachel was vacationing with her college girlfriends and their significant others in celebration of their collective 40th birthdays this year (fun). They’d be staying at a beautiful resort, going out for a couple of dinners, and spending a day on the water. I also wanted to help her figure out what to wear to the airport—helps you get in the vacation state-of-mind. Usually I style the most important outfit first, but since there wasn’t one big event, I started with the clothes that Rachel was most excited about.
Pull pieces that get you in the vacation mood
I have a handful of shirts that I keep specifically for Ocracoke. I wear them only once a year, but they’re worth storing in my studio apartment because when I pull them out of the plastic bin from underneath my bed, I immediately start reminiscing on past vacations. I think about where I was when I wore them, the people I was with, the way I felt. These tees in various shades of blue transport me to the Outer Banks.
Ahead of our styling session, I asked Rachel to pull a few things that she’s been wanting to wear. A Bahía María set she’d bought in St. Barts, a beaded Staud dress, and a Monday Swimwear bikini with matching sarong. I focused on these pieces, and then pulled in other items from her existing wardrobe to style the looks.
Test out your outfits
This is an essential step if what you’re wearing on vacation is an integral part of the trip. Whenever I don’t do this, I end up feeling frustrated because I’m not able to actualize a look. I’ll be standing in my room with an incomplete outfit thinking, “if only I packed that dark blue scarf…”
Rachel and I booked two hours to put together her outfits. I recommend giving yourself the same amount of time to style your own looks because when you’re not rushed, you’re more inclined to ease into play. Think of this as dress up.
This was the first look I styled. Since the top had such a pretty floral appliqué, I skipped the necklace and chose these sunburst earrings. I like how the gold complimented Rachel’s mermaid hair and glowing skin.
Turns out this was Rachel’s most complimented outfit (ever!). I added a chunky bangle to balance out the skirt’s volume, then completed the look with a crochet shoulder bag.
This dress had such beautiful floral detailing. I just wanted to play it up. I pulled this chunky beaded necklace to compliment the square neckline and reference the red. I liked the idea of a clutch, and selected this one because the materials felt beachy.
I paired the dress with chunky block heels. I wanted to make sure that Rachel felt at ease in all the outfits so that she could just enjoy being with her friends.
Here I layered on some beaded necklaces that Rachel wouldn’t mind getting wet. The pairing complimented the colors in her suit and sarong, and added a playful touch to her outfit. How cute is that hat?!
We liked the pairing so much, I kept them for the outfit I styled Rachel in for a Substack live she did with
about ambition, burnout, and wellness.Put together an airport outfit
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