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I Work in Fashion—These Are the Stylish Pieces I Always Pack for a Warm-Weather Vacation

By Swedan Margen

I Work in Fashion—These Are the Stylish Pieces I Always Pack for a Warm-Weather Vacation

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

Vacation outfit ideas

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

J.Crew

Crochet Beach Polo Shirt in Cotton

j.crew, Crochet Pants
Martino White Crochet Dress

Ciao Lucia

Martino White Crochet Dress

Button Up Coverup ~ Yellow Crochet Xs

Show Me Your Mumu

Coverup

Mitir Cotton Mini Dress

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

Hunza G

Cassie Beaded Bikini Set

Solid & Striped, Veronica One Piece

Solid & Striped

Veronica One Piece

Jade Swim Rounded Edges Top

Jade Swim

Rounded Edges Top

Jade Swim Incline Bottoms

Jade Swim

Incline Bottoms

Coverup

Vacation outfit ideas

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.

chan luu, Caftan
lemlem, Elina Caftan
Mustard Odilia Terry Dress

OAS

Mustard Odilia Terry Dress

minnow, Coverup

Matching Set

Vacation outfit ideas

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.

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I Work in Fashion—These Are the Stylish Pieces I Always Pack for a Warm-Weather Vacation - Vanity Fair Fashion