Clockwise from top: V-neck linen t-shirt / Grey maxi dress / Black dress / Madewell shirtdress / Victoria Beckham dress / Current Elliott stiletto / Alexander Wang t-shirt / Jimmy Choo 'Youth' boots / Alexander Wang blouse / Equipment lace shirt / Sweater / Louis Vuitton coat / Alexander Wang tank / Nike Sky Hi / Christian Louboutin Décollete / Silk scarf / Ancient Greek Sandals / Christian Louboutin espadrilles / Linda Farrow sunglasses / Eres maillot and bikini / Hanro silk leggings / Prada skirt / Rimowa Topas suitcase
My husband introduced me to the joys of the Rimowa Topas, which we share during vacations. Before that, I traveled only with a little Adidas book bag my mom gave me- originally my aunt's, it carried Mom through law school, internships, the birth of a son, and so on. My travel steamer took up half the space, and the only way I could carry it was a single shoulder strap, but that sturdy thing accompanied me from London to Paris to Berlin, Istanbul, Russia, Southeast Asia, India and Iceland. At one point, I ditched the steamer and used a laptop carrier instead; sheer sentimentality rescued the Adidas from obscurity, and it remained my go-to travel bag until my cats decided to use it as a toilet.
When far from home and surrounded by strangers, you're judged on the merits of your external appearance, so it's important to be nicely and respectfully attired. This precludes extreme modes of dress- somewhere between J. Lo in a velour tracksuit circa Ben Affleck, and J. Lo wearing Marchesa to a sports bar. I've bypassed TSA checkpoints because an agent liked my shoes, and gotten free bottles of wine in lounges, just for brushing my hair. Once I talked to John McCain for ten minutes in an airport, and though I didn't recognize him until later, I was happy not to own any Victoria's Secret PINK sweats then.
If traveling by car, it makes sense to be more casual; a t-shirt and full skirt are comfortable and virtually wrinkle-proof. I'm so sick of the tunic + white pants + Tory Burch flats combination- it's so old rich white lady! The wardrobe above is seasonless and multitasking, as close as I could come to the clothes I wear when traveling. Try using a maillot as a top, a lace shirt as a cardigan, and silk scarf as a skirt or cover-up. Oh, and packing cubes make me roll my eyes. A repurposed cloth drawstring bag is fine.
Pack more or less, depending on the destination and length of trip- my longest trip was 90 days, and I did laundry four times thanks to the contents of that little bag. Of course, underwear and bathing suits should be washed more frequently, in the sink, then hung to dry; all you'll ever need are seven pairs of underwear and two bras. I usually pack three pairs of socks, but wish I'd brought more for Cambodia and India. They keep feet clean while sightseeing, and also prevent monkeys from biting your toes.
Sometimes I travel with a purse, other times I pull a Carine Roitfeld and stick everything in my pockets. I've never used an RFID blocker or money belt and don't plan to. Toiletries should be especially minimal when traveling long distances. A little oil for cleansing, moisturizing, and conditioning; a sustainably harvested wooden hair brush, bamboo toothbrush, glass jar of baking soda, homemade eyeliner and unpackaged soap make an aesthetically-pleasing, TSA-friendly zero-waste travel kit. No mess, no spills- just leave the safety razor at home. UPDATE: So far I've been able to take a safety razor in a carry-on to the US, Norway, Thailand, Singapore, Canada, and Indonesia.
Below are a few sample outfits appropriate for almost any country or culture:
here and here.