Jennifer Alfano spent almost 20 years working for Vogue, Harper’s Bazaar and Lucky before creating her eponymous jewelry line in 2013. Writing and editing remain a big part of her life as the founder of The Flair Index, a newsletter all about fewer, better things. It’s only fitting that she manages to pack for 10 days in Italy with just hand luggage in tow. —C.S.

What’s your go-to luggage?
A 20-year-old Tumi carry-on. I should probably get a new one, and when I do it will be another Tumi, but it’s in excellent shape and isn’t that the point of buying something that is meant to last? My trip to Italy is 9 nights and I can make it with my Tumi and a tote (I did Ireland in March for a week with two carry-on pieces and a bunch of inclement weather clothing). I do need a new tote. The bag I have my eye on is the Tumi Voyageur Contine Weekend Bag, because it has a space for shoes at the bottom and my running shoes are always the one thing that never fits.
How do you approach the basics?
I am fairly minimalist in my style and I believe in fewer better things, so my vacation wardrobe is something that has slowly been coming together for the last couple of years; I like to update it with a couple of new pieces, but you will see me wear the same thing again and again.
I always start with a color palette (not that there is much color variation in my closet to begin with). For my Italy trip it is white, black, and neutrals—khaki, army green, gray. On the plane, I’m wearing James Perse black linen pants with the Leen tee (the weight is so good), a comfy breathable State of Cotton sweater, and Birkenstocks (with socks once we’re airborne so my feet don’t freeze). I’ll pack a pair of Matteau khaki linen trousers, white Agolde denim shorts and a nice pair of black Bermuda shorts I bought from Dries Van Noten a few years ago. Shirts: Kule striped tee that doubles as a coverup, a Nili Lotan crochet tank I bought two years ago and still haven’t worn, my made-to-measure Micky Paris military shirt and my Frances de Lourdes white button down, plus a couple FDL sexy tees. Two bathing suits: A bikini and a one-piece from Eres. I’m older, I don’t care, I still want to wear a two-piece. Two caftans: One I bought last year at Coqui Coqui; this one from Su Paris and one pareo, which doubles as a skirt. Then evening clothes: This is where I want more variety and it’s where I’ve updated things. I bought a white eyelet Toteme dress, this crinkled Toteme top that matches a skirt out of the same fabric I bought two years ago, and a pair of Toteme silk pajama pants. I have a thing for pajama pants; they’re elegant and comfortable, a win-win. Two silk slip dresses, one James Patrick organic (good on its own or underneath my Su Paris caftan), the other Nili Lotan. One lightweight off-white linen white blazer from Vanessa Bruno. Everything goes with everything and it’s a fun challenge to create different outfits.
Are you a roller or a folder?
Both—and a medium Muji nylon gusset case is a game-changer. You can roll/fold your clothes and really cram them in there (in a nice way). It also keeps them from wrinkling. It’s fun to see how much you can actually get in one.
Any other packing tricks or hacks?
Don’t put anything in a checked bag you would truly be upset to lose. And if you do check your luggage, have a change of clothes on you just in case.
What’s your shoe strategy?
As many as I can fit in! (And usually that means taking some of my husband’s space in his carry-on because he travels so light.) But honestly, I will be taking two pairs of A. Emery sandals, a pair of Toteme sandals and classic Manolo Blahnik Susas for evening. I will wear my Birks on the plane.
How do you think about accessories?
A graphic-printed silk head scarf is a quick way to add visual excitement to an outfit because you can wear it a la Jackie O, tied at your ponytail, or wrapped around your bag. My day bag is a flat raffia bag from Vanessa Bruno I found in Ireland, and my DEL’EP phone and eyeglass cases; for evening, I’ll bring my Bottega Veneta mini Jodi. Then jewelry, since I design it, I want to travel with some, but it all has to be on my body when I leave or fit into my tiny old Vuitton Bijou case. I’m taking my XL Silver Mariner Necklace and Bracelet and for gold—a Tahitian pearl drop and my pearl Bullseye pendant on a long chain (love a long chain and bathing suit/caftan combo), my Half-Link hoop earrings with the Large Link and Pearl attachments, and my Oval Signet Ring.
Do you have a great travel hat?
Not really. I have a couple of hats, but what is coming with me is a straw hat I bought in Venice four years ago, because it was inexpensive and I don’t care if it makes it back.
What’s always in your dopp kit/toiletry bag?
I have a Muji clear case for carrying my liquids. I try to stick to my skincare regimen as much as possible. There is a travel-size Bioderma Micellar water for taking off makeup and to use as a gentle skin cleanser, my Vintner’s Daughter Active Treatment Essence (post cleanse), and my Environ Youth Essencia C-Quence Serum and Antioxidant Defense Crème which I get from Knockout Beauty and mix together for moisturizing. Then Supergoop sunscreen for the face/neck (I buy body sunscreen wherever I go; it’s too much to carry). Makeup is Westman Atelier Vital Skincare Complexion Drops, Beauty Butter Bronzer, Charlotte Tilbury Pillow Talk mascara, a Chanel red lipstick if I feel like dressing up; and H Perfumer London’s Indian Wood perfume.
On a plane, what essentials does your carry-on always contain?
Glossier Bomb Dot Com in Rose and Rosebud Salve, Afrin, hand cream, a good book, and Cheez-Its. They are my traveling snack splurge. Never get on an airplane without them.
What’s your pharmacy kit?
I’m married to a doctor so you think I’d be more organized in this area, but beyond Advil, Tylenol and allergy medicine, nothing else. I guess I rely on him to figure it out.
Do you have a travel uniform?
When it’s hot, James Perse linen pants, a Leen tee, and State of Cotton sweater. For all other times, my Frances de Lourdes scuba pull-on Astrid pants, long sleeve black Elise tee and navy cashmere Zoe shirt—three pieces that you can wear endlessly in many different ways. Worth every penny.
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