14 Clothing Items That Made Packing (and Dressing) For Vacation Easy

vacation outfit ideas

Designed by Byrdie

A few months ago, I took off on an adventure to Italy with my husband and two small children. After weeks of research and listening to Rick Steves' podcasts, we finalized our itinerary to hit five areas in Italy.

A few years ago, I'd travel with the largest suitcase size available, with too many shoes and garments to count. Since then, I've evolved and mastered the art of traveling lighter, especially with kids when space is limited. Instead of hauling everything in my closet, I stick to items that are equal parts cute and multifunctional. If you're planning a trip in the near (or far) future, I'm rounding up all the clothing pieces I took on my trip, plus how I styled them to save precious suitcase space. Read ahead for more.

Classic Black Dress

A classic black dress with spaghetti straps will get you everywhere, from sightseeing to early dinner reservations. I loved this gorgeous maxi-length dress with a V-neckline and a smocked bodice. This was my go-to daytime dress, and combined with a woven hat and leather sandals, it was the perfect outfit to have my husband photograph numerous times throughout the day.

White Linen Dress

This dress belongs in the picturesque landscape of Tuscany, making its name (the Tagliatelle Linen Dress) very fittingThe contrast of a fitted corset top, lace details, and a looser skirt create a lovely romantic effect without being overwhelming. I completed the look with black and white wedge espadrilles to go full Gwyneth Paltrow in The Talented Mister Ripley.

Light Wash High-Rise Jeans

These jeans somehow go with everything and look better the more often you wear them. I usually pack one pair of light blue jeans to wear on colder nights or during the day with a bodysuit and crossbody bag.


Speaking of bodysuits, I opted for one with a square neckline for a classic silhouette. I packed one black and one tan version to mix and match with shorts or jeans. Bodysuits are great to pack in your suitcase for longer trips since they don't take up a lot of room and can be worn day or night, depending on the styling. Think: denim shorts, a crossbody bag, and ankle sneakers during the day, and white flare denim with a clutch for the evening.

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Oversized White Button Down

When it comes to a classic white button-down shirt, it's all in the details. I opted for an oversized version to look less preppy and more casual. For beach days, you can wear this buttoned-up with denim or open and breezy over a fitted dress, swimsuit, and wide-brim hat.

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Plain White T-Shirt

I've tried many white T-shirts for years, and one of my top five is this vintage-looking cut from Reformation. It has a perfectly relaxed fit with a neckline that isn't too tight and sleeves that are the perfect length. I recommend ordering one in black and one in white to add variety to your vacation wardrobe.

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Satin Slip Dress

A slinky slip dress with sandals and a drink in hand is always a good idea. This bias-cut midi dress from Free People drapes beautifully and features a beautiful open back. Wearing this dress with heels over cobblestone streets may have screamed tourist, but I took the risk anyway. During the day, I paired it with comfy white sneakers.

Oversized Blazer

I love the contrast of a delicate slip dress paired with an oversized blazer and strappy sandals. I paired this look with a gold locket necklace for a night out in Milan.

Off-The-Shoulder Dress

A curve-hugging dress is a must to pack for fancy dinners or if you're going to a wedding. From the bustier to the off-the-shoulder details, this was the perfect piece to pack for dressing up.

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Crossbody Belt Bag

I loved this crossbody belt bag, which had the same functionality as a classic fanny pack but felt much cooler. This one is lightweight and has plenty of compartments for storing little things. 

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Denim Shorts

A solid pair of denim shorts is the item I reached for the most in Italy. This high-rise pair from Everlane is made from organic cotton and are perfect for casual sightseeing activities. Pair with a white button-down or a plain black t-shirt and wear on repeat.

Floral Day Dress

A flirty sleeveless dress was perfect for strolling the streets of Venice and exploring the fishing villages of Cinque Terre. The cinched waist and lightweight crepe fabric were comfortable and stylish for daytime exploring.

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High-Top Sneakers

These sneakers are a great way to make dressy items look more casual, and I paired mine with a slip dress to look more relaxed overall. If high tops aren't your thing, opt for low sneakers for a similar effect.

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Woven Beach Bag

A khaki woven bag is the perfect goes-with-everything accessory to have in your luggage. I loved this one, which has a zipper, so you don't need to worry about items spilling out of your beach bag.

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