My Philosophy, Tips, and How I Went About Packing for Italy

Plus links to my favorite items I'm bringing with me.
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Remember when Leslie shared her carry-on with Jonah for five days in Europe? That's not me. As appealing as it sounds to embrace the simplicity of packing light for our three-week trip to Amsterdam and Italy, I also need to be realistic. When I posted an IGTV of my packing process over the weekend, I was flooded with DMs of follow-up questions, but also messages from friends concerned by the sheer volume I'm bringing, asking if I needed a packing intervention. But here's the thing: I enjoy packing for trips. In the same way others prioritize minimalism, I enjoy the process of stepping my outfits up a notch when I travel and never needing to worry about whether I have something cute to wear out to dinner. Yes, I'm a bit over-packed, but I'm also in a really good place. Normally at this point, I'm in a full panic, double- and triple-checking that I have everything packed for myself and Sloan. But after spending the previous weeks prepping and a good portion of the weekend packing, I feel confident about my packing strategy and the items I'm bringing. Here are my tips and favorite items I'm packing for three weeks in Italy:

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Create a Doc in the Weeks or Days Leading Up to the Trip: A few weeks ago, I created an initial list in an email draft (a Google Doc would also work) of everything I needed to pack for myself and Sloan, organized by clothing, accessories, beauty, and tech. That way, any time I remembered something in the middle of the night ("Tweezers!") or at work ("Bedtime books for Sloan!"), I added it to its category to ensure I didn't forget a thing.

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Make a Pile of "To-Bring" Clothes: For two weeks leading up to the trip, anytime I did laundry, I added clothes I wanted to bring to a designated pile. That way, I had a starting point of clothes I was most excited to bring, and could ensure that everything I truly needed was clean and ready by the time I started packing. 

If You Need Trip-Specific Clothes, Consider Renting: One night in Italy, we're doing a Fellini-themed night to celebrate a friend's birthday. We're hiring a string quartet (!) and all wearing black tie, with women in gowns. Because I don't own a gown, and really can't imagine another time when I'll need to wear one, I rented a sequin option ahead of time on Rent the Runway. Follow along on social to see which one I picked! ;)

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Roll Items and Use Packing Cubes: For years, I refused to use packing cubes, but finally tried them out for this trip and, as of this point at least, I am a full convert. Especially for a long trip, it keeps everything so organized. I also rolled my clothes, as opposed to folding, for this trip to maximize space and it's amazing what a difference it makes. 

Pack Your Hat But Bring a Hat Clip: This is a fairly random tip, but one that I envision making a large difference on our trip. I initially thought I'd wear my hat on the plane, before a reader suggested I pack it and fill it with smaller items like socks. I still purchased a hat clip so I can clip it to my bag when we're walking around during the day. 

Pearl Hairclips, Puka Drop Earrings (similar here and here), Gold Hoop Earrings, Tortoiseshell Clip

Pearl Hairclips, Puka Drop Earrings (similar here and here), Gold Hoop Earrings, Tortoiseshell Clip

Accessories Are the Best Way to Make the Most Out of an Outfit: I made sure to bring ample hair accessories and jewelry on this trip so that, even if I'm wearing variations on the same linen outfit, I can throw on a bright lip and statement headband to switch things up a bit. (I've included links to headbands below!)

If You're Traveling to Different Climates, Keep Those Clothes Separate: Amsterdam is supposed to be rainy and chilly, while Italy is sunny and hot. Since we'll only be in Amsterdam for a few days, I'm keeping Sloan and my outfits in my rolling carry-on so I don't have to dip into my Italy hot weather clothes, and can avoid repacking.

Bring the Same Colored Underwear: Look, I'm not saying skin-colored underwear is the sexiest thing in the world, but it is as versatile as it gets. Jess, Leslie, and I all make sure to pack exclusively nude thongs when we travel (the things you know when you share your life online), because the last thing you want to happen is get to the last day and realize you only have a white dress and a black thong left. I've sworn by these from commando for years, though I recently tried and loved these from Calvin Klein as well. 

Set Aside the Clothes You Plan to Wear On Your Flight: I always set aside what Sloan and I are wearing on the flight ahead of time so I never have to scramble (or unpack) the day-of. We'll be sharing our team's go-to travel outfits later this week!

From left to right: Cuyana, Mark Cross (similar here), Theory belt bag (similar here)

From left to right: Cuyana, Mark Cross (similar here), Theory belt bag (similar here)

Be Strategic About the Bags You Bring: I'm bringing three bags to Italy—a neutral large tote for the plane, a crossbody bag, and a belt bag, plus luggage. 

Tote: A zipper is a must on an airplane tote so nothing tumbles out during takeoff and landing. I've owned this one from Cuyana for years, and it's aged amazingly well. I fill it with small bags that corral Sloan's snacks, first aid (I always have Advil, Alka-Seltzer, and band-aids on me), and lollipops for Sloan... and also me. I also bring a pared down set of makeup, including a refreshing spray, lip balm, face moisturizer, and serum that I reapply during the flight when I think of it. 

Crossbody: I've had this Mark Cross bag for years (similar here) and had it refurbished in the weeks ahead of the trip to ensure it was in top shape. 

Belt bag: I bring a belt bag from Theory (similar here) anytime I travel, so I can walk around with everything I need, but be free of a bag on my shoulder. 

Suitcase: I've owned the same Delsey Paris Suitcase (on sale!) set since I purchased it for G and my honeymoon in Italy. 

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Last week, I shared all of the items I purchased for my trip and some of it simply didn't work. For example, I really wanted this Faithful the Brand jumpsuit to look good, but it was too dark and by the time I realized it came in white, it was sold-out. (Instead, I grabbed this top!) It was lucky that I was able to pick up a few amazing linen playsuits and additional pieces last week. Here are a few of my favorite and most-asked about pieces I'm bringing: 

Shoes from left to right: Cupcakes and Cashmere Heels, Cupcakes and Cashmere Slides, Steven Alan Sandals (similar here), &OtherStories Slides (similar here), Jenni Kayne Slides (similar here), Beatrice Valenzuela Slides, Nike Sneakers, Golden Goose Sneakers

Shoes from left to right: Cupcakes and Cashmere Heels, Cupcakes and Cashmere Slides, Steven Alan Sandals (similar here), &OtherStories Slides (similar here), Jenni Kayne Slides (similar here), Beatrice Valenzuela Slides, Nike Sneakers, Golden Goose Sneakers

Shoes: My strategy for shoes this trip is similar to the approach I took to packing shoes for G and my trip for Paris two years ago. I'm bringing plenty of comfortable slides and sandals, since we'll be spending the majority of our trip at the house we rented, in addition to two comfortable pairs of sneakers, and one pair of dressier heels. See links in the caption above!

Accessories: I'm prioritizing hair accessories for this trip, packing several Jennifer Behr headbands (in black silk, braided, with roses, and in leopard print), a striped silk scarf, an Ace of Something hat (similar here), a vintage Chanel bow, silk scrunchie (similar here), and pearl and tortoiseshell hair clips, which I'm corralling in this bag I bought on a trip to New Orleans. I'm also bringing three pairs of sunglasses, since we'll be spending so much time outside—aviators from AMAVII (similar here), this pink pair from Celine (similar here), and this black pair from Celine (similar here)—and this belt, which goes with almost everything I'm packing.  

Bathing Suits: The house we're renting has a pool so I'm very excited about swimwear. I've packed sets from Summer Salt, L*Space, and Montce (I love this ribbed bikini top and bottoms). I also picked up the cutest "bikini bag" from Old Navy, which I'm using to pack all my suits. 

Linen Suits: I'm bringing a variety of outfits (as you can see from my enormous pile of clothes...), but some of my favorite pieces I'm bringing are linen suits I picked up from LVIR at The Row in downtown L.A.

Flowy Dresses: I'm taking a page from my friend Stacie's book and bringing several flowy dresses, including this Daily Sleeper dress and a few from Doen, including this new one. I love this black dress, which I found for under $100 on Shopbop!  

Sweats: Almost all the sweatpants and sleepwear I'm bringing are matching sets from The GREAT since they're comfortable, but cute enough to wear in the morning while I'm drinking coffee. 

P.S. I started writing my tips for packing for Sloan here but realized I had too much to add! I'll be sharing a separate post with my tips for her later this week. x