Tessa Faye O’Connell is a contributor known for her work at various fashion houses, specializing in media and public relations, currently working at Coach as its global PR director. She’s a mom of two, working to expand her influence in the fashion space through styling while also just making it out the door on time.
If you think I have an outfit folder for day-to-day dressing, you better believe I have a process for getting ready for break or a beach vacation. I hate overpacking or feeling like I’m wasting any time other than relaxing with my family—and I meticulously do a try-on of all items and coordinate to bring accessories that can mix and match with most everything. Where I used to worry about just me, now I have to ensure my beach bag is big enough for all the kids’ toys I’m lugging, and my outfits aren’t going to fly off chasing after two girls in the pool, or someone at my lap at dinner.
While it takes some work on the backend, the reward for being prepped and ready to go is well worth it to feel good in what I choose to wear, but also to feel functional. Having some go-to outfit formulas like the ones below makes packing a bit easier. Plus, what is better than being in warm weather, flowy dresses, and relaxing for that trip (not vacation) with your littles when you already know what you’re going to wear.
Crochet Pieces
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Crochet pieces are some of my favorite pieces for traveling as they are so cute, wearable, and you never get to wear in your day to day life.
J.Crew
Crochet Beach Polo Shirt in Cotton
Ciao Lucia
Martino White Crochet Dress
Show Me Your Mumu
Coverup
Akoia Swim
Mitir Cotton Mini Dress
Bathing Suits
Underneath it all: My favorite bathing suit roundup. Easy, stretchy, comfortable.
Hunza G
Cassie Beaded Bikini Set
Solid & Striped
Veronica One Piece
Jade Swim
Rounded Edges Top
Jade Swim
Incline Bottoms
Coverup
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I live to purchase and collect coverups, and continue to gravitate and come back to styles that are comfortable and wearable, especially when chasing around two little girls who are anything but chill on vacation.
OAS
Mustard Odilia Terry Dress
Matching Set
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live in these Chann Lu sets on vacation, they are multiple outfits in one, can be worn together or as separates as an outfit or to the beach—my go to always.
apiece apart
Gustava Button-Up Shirt
Leset
Niko Oversized Button Down
Leset
Niko Crop Pocket Pant
Mini Dress
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I love this one by Faithfull the Brand. Everything they do is perfect for summer and vacation.
Faithfull The Brand
Palomar Mini Dress Espresso
La Maregold
The Ophelia Dress
Reformation
Joliette Dress
Flowy Top
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A flowy top to throw on with anything from linen pants to jean shorts is a must. I prefer a fun printed or colorful style that I don’t normally wear to the office.
Little Moon
Tybee Linen Blouse
Banana Republic
Archive Reissue Popover Shirt in Linen
ciao lucia
Nita Cherry Blossom Silk Top
azeeza
Plath Cotton Voile Top
Alix of Bohemia
Priya Blouse
Printed Dress
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A good printed dress is necessary on vacation (and maybe always).
SZ Blockprints
Rina Dress in Fleur Print
Natalie Martin
Fiore Maxi
THE GREAT.
The Sundrift Slip Dress
Shorts
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Shorts can be worn over a bathing suit, can dress up if needed for a more casual dinner out or to breakfast in the morning with a T-shirt.
Reformation
Fern Satin Shorts
Mother
The Flutter Fray Jean Shorts
leset
Kyoto Carpenter Short
White Dress
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Viva la white dress on vacation after sitting outside in the sun all day (under a hat you still get a glow.)
Faithfull the Brand
Fiora Midi Dress Fresco Lace White
Matteau
Broderie Cami Midi Dress
Mini Bag
You can throw a mini bag into your travel bag, which should always be a Dagne Dover carryall or backpack.
the horse
Fin Drawstring Bag
Loeffler Randall
Kenzie Bag
St Agni
Lattice Weave Mini Bon Bon Bag – Coffee
Hat (and Sunscreen)
Cover that beautiful face of yours!
Janessa Leone
Felix Bucket
Hat Attack
Clarissa Surfer Hat
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