What I Packed for a Wedding, Beach Days, and Broadway in One Suitcase

A mix of vintage finds, easy summer staples, and event-ready pieces carried me through 10 days back East.

Grace O’Neill Dougherty wearing different summer outfits
(Image credit: Grace O’Neill Dougherty)

It may sound insane, but I always love packing for a trip. Especially when that trip is back to New York for my best friend's wedding and to see my family in the Northeast. It’s pleasing to see all the summer fabrics—silks, cottons, organza —mix with all the best summer colors—soft yellows, blush pinks, hues of different denim washes, and lots of white — piled into a suitcase together. It lets me know that despite the blissful mid-70s temps we’ve been getting here in LA, I can expect to be hit with a wave of heat and humidity soon, and I pray that my skimpy fabrics will get me through the worst of it.

Grace O'Neill Dougherty styles a royal blue dress for her East Coast summer

(Image credit: Grace O'Neill Dougherty)

Ahead of my journey, I planned outfits to make it easier for myself, something I never do, but thought I’d experiment for the sake of this article and my sanity. I planned 11 outfits for my 10-day stint home.

Last summer I got my first Eres bikini, which is my go-to for beach days. The quality will stand the test of time. I’d pair it with these pants from J.Crew and a straw bucket hat for ultimate sun protection as my Irish skin burns easily. I’ve been wearing these boat shoes from J.Crew for a few months now, hoping they’ll be perfectly worn in by the end of summer. For beach bags, I’m usually partial to a boat and tote or these beautiful raffia totes designed by Olivia Irja for Sorbara’s. In this photo I chose my floral Circle Bag designed by Giovanna Flores. Similar here. My flip-flops are from Carmen Amsterdam, which I wear almost every day. The silver color is a great contrast on my pale skin. I also love these from A. Emery, which you’ll see sprinkled throughout all these looks.

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Grace O'Neill Dougherty wears colorful pants with a bikini top and flip-flops

(Image credit: Grace O'Neill Dougherty)

Grace O'Neill Dougherty warms up a casual look with a black roll neck sweater

(Image credit: Grace O'Neill Dougherty)

I’ll always carry a rollneck sweater from J.Crew in the northeast for the inevitable cooler evenings. I prefer the men’s fit to the women’s. Also, for colder temps, which are expected in Nantucket, I’ve packed my army fatigues, which never fail me. (Similar from re/done) They have been with me since 2019 and have become the softest pants I own. I like pairing them with something more feminine on top like this Jil Sander long sleeve. Similar here and here. My current favorite bag is this from Valesque. A lot of girls have asked me if it’s The Row, which is always a great sign. My favorite ballet flats are from Porselli in Milan, which Alex Mill sells a version of if you don’t want to wait a few weeks or months for the ones they make custom for you. They are worth the wait, however…

Grace O'Neill Dougherty pairs army fatigues with a feminine top

(Image credit: Grace O'Neill Dougherty)

Grace O'Neill Dougherty styles a graphic tee with a blue Phoebe Philo skirt and black wedges

(Image credit: Grace O'Neill Dougherty)

Chloe SS 2005 by Phoebe Philo is one of the few collections I’m obsessed with finding at the moment. I found this skirt on The RealReal (Doen has a silk option in a similar blue color) and paired it with a vintage Art Deco tee I got at Sorbara’s a few years ago that is now perfectly thrashed. While we’re on the topic of that exact shade of blue, I also got this Dries Van Noten slip dress on The Real Real and paired it with some satin Louboutins, also secondhand and my first pair of red bottoms. Since writing about dresses, I can’t stop buying more! The new Eckhaus Latta x Mango collection has some Dries-like patterns, like the one on this skirt.

I found a resin bracelet from Balenciaga SS 2012 (similar from Completed Works) in LA a few weeks ago. It’s been great to throw on when I feel my outfit needs a little something more. These Prada wedges are the best finishing touch.

Grace O'Neill Dougherty styles a button-down and jeans, both from Buck Mason, with black heels

(Image credit: Grace O'Neill Dougherty)

I have a few events to attend in New York and wanted to opt for something classic and not too fussy, as I’m only in town for a few days. My button-down and jeans are both from Buck Mason. I’ve raved about these jeans before and always get compliments on the fit. I paired it with a simple black satin Manolo and my favorite Sophie Buhai drops. The ones I’m wearing are a style from a few years ago, but these (and these) styles are similar.

Grace O'Neill Dougherty styles vintage Dries Van Noten and Gucci for the theater

(Image credit: Grace O'Neill Dougherty)

For my night at the theatre, I’m bringing a Tom Ford Gucci skirt from 2003 (similar here and here) and a Dries jacquard jacket from the late 90s, along with my trusted Porto pouch.

Grace O'Neill Dougherty models Cleo's Story floral dress

(Image credit: Grace O'Neill Dougherty)

Cleo Camp’s newest creation, the Story Dress, is made with deadstock fabric from Liberty London. I visited her studio before my trip and tried on both the red and green colorways. I had a terrible decision to make because they are both insanely desirable. I ultimately went for the red and, of course, regretted not getting green the moment I pulled out of the parking lot. The red was great for wearing to dinner at Michael’s and then to Broadway to see Death of a Salesman.

I’ll be wearing the Cleo tee all summer long in sunshine, splash, and white. The top's versatility is the best part. I typically wear it boat-neck, but I love the option to wear it scoop-neck if I’m feeling scandalous on a night out. Cleo’s creativity is endlessly inspiring to me, along with the images she makes for her brand with friend and collaborator Maddy Rotman. Together they focus on capturing the in-between moments. Cleo’s designs are grounded in her upbringing, each piece always paired with a touching story from her childhood. Camp tells me she grew up wearing Liberty prints at the beach with her grandmother: “She used to sew pajamas for me with the same fabrics”.

Grace O'Neill Dougherty styles an all-white look including a scarf worn as an oversized sarong

(Image credit: Grace O'Neill Dougherty)

My favorite look I packed was this all-white get-up. The pants underneath the linen sarong (which is really a massive vintage linen scarf tied) are from Baserange, and they are in my top three most worn pants in the summer months for the past few years. I don’t fret when they get wrinkled, as this blend of cotton looks chic when it’s worn in. My top is again, vintage Jil Sander from the 90’s, but this Comme Si shirt would be a nice option, too. I’ve set alerts for when this deep V comes back in stock.

Some items I wish I’d had for my trip are this baseball tee from Leset, this v-neck from Los Angeles Apparel, 6397’s Fleecey Track Zip Up, the Prince Blouse from SC103, the Kipling top from Emily Dawn Long would have been helpful for the unbearable humidity in upstate New York, and the Santo Shirt from Giovanna Flores for morning strolls in Nantucket.

Grace O'Neill Dougherty
Contributing Editor

Grace O'Neill Dougherty is a writer and actress living in Los Angeles. She authors the popular Substack Jelly Sandwich.