in her shoes

How to Dress for Work When You’re Always Traveling

Photo: Gabriela Herman

As Director of National Partnerships for Airbnb, Janaye Ingram is always traveling. Ingram’s job involves helping Airbnb create an inclusive experience for both hosts and users, and fight discriminatory practices. So on any given day, she might be flying off to speak at a conference on the other side of the country — or possibly the other side of the world.

It’s a big job, but she’s used to it. Prior to Airbnb, Ingram was the national executive director at National Action Network, a civil-rights organization. She’s also one of the founding members of the Women’s March, where she served as head of logistics for the first march in 2017. And before that, she cut her teeth working at nonprofits across New York and New Jersey.

The Cut managed to catch up with Ingram recently at Airbnb’s offices in New York. Read on to hear about her best packing tips, the shoe she’ll always wear, and why she doesn’t look to clothes to give her confidence.

On the shoes she wears every day: I hate overpacking. Shoes take up a lot of space in a suitcase, so I bring one good pair of boots. Last fall, I wore Hudson London’s Crispin ankle booties everywhere. I also found a pair of Seven Dials over-the-knee boots that were so comfortable and versatile that I bought another pair towards the end of the season — plus pairs for my mom and sister!

On going out after work: Back when I was in Washington, D.C., I’d go to politico events, and they’re usually the same dress code as what I wore to work. But now that I’m in tech, it’s more relaxed and my outfits skew casual. If I have to go out, I’ll dress for the day and change my shoes and accessories. I love chunky bracelets. While they’re annoying when you’re typing away, they’re great for after-hours.

On big meeting outfits: I remember speaking on a panel at the White House with Michelle Obama, and one of my friends was trying to help me pick out an outfit. She kept showing me pantsuits, but none of them felt right. They might radiate a certain power but I’m more comfortable in a sleek dress, and that’s what I wound up wearing. I typically shop at department stores with lots of options and don’t look for a specific designer. That said, I find that Amanda Uprichard, Dress the Population, and Black Halo work well for my body and the types of events I attend.

Photo: Gabriela Herman

On traveling for work: After I left my job as national executive director at National Action Network, I spent a lot of time hopping between countries. I learned how to pack for longer periods of time in a carry-on. And with my current job, I’m usually going from plane straight to my first meeting. For the sake of efficiency, I have a time-consuming ritual where I try everything on before I pack — that’s how I know my pieces work well together, especially if I’ve never worn them together before. I also love packing cubes! They help me separate my clothes in a way that also allows me to stay neat while traveling.

On speaking engagements: When I need to speak, a jumpsuit and a great pair of pumps is my first option. It makes moving around a lot easier and is better for sitting on a stage. I use Rent the Runway a lot. Typically, there are a lot of photos at those types of events and I don’t want to be photographed in the same outfit, so Rent the Runway has been super helpful.

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Alice + Olivia Jeans Gorgeous Wide Leg Jumpsuit

On who she dresses for: While I dress for me, I know first impressions matter. I don’t want my clothing to be a distraction for me or others, so I try to be slightly more formal than what an occasion calls for. My outfits are also determined by my mood and the weather. I sometimes dress up just because it makes me feel good or because the weather is nice — even if I don’t see anyone outside of my 15 or so work colleagues.

On her style evolution: My look is classic but still on-trend. I actually still have pieces in my closet that are over a decade old and they don’t look outdated! But as I’ve grown professionally and personally, my style has become more sophisticated. In high school and college I used to wear a lot of black and my friends would joke that my uniform was a black shirt and jeans. Now, I like to play with colors and patterns. I incorporate pieces that are bolder than what I would have worn previously.

One lesson that I learned was to invest in certain pieces. I’m a bargain shopper and hate paying full price for anything. When I was younger, I’d buy a lot of disposable, cheap pieces that last a season or less. I’d do it with purses especially. I’d buy a cute handbag that wasn’t made of quality materials and a month in, it would start falling apart. Now I spend a bit more and I have a few Kate Spade and Rebecca Minkoff bags that I really love.  

On the last three things she bought: I recently returned from a trip to Ghana for the Year of Return and I wanted to wear Ankara prints while there, so before my trip I bought some items from a retailer called D’IYANU. The fit was really great and I received tons of compliments. I also ordered Schutz mules and wedges. I love their shoes and even though summer is over, I’d been eyeing the sandals for a while and they were on sale! And then I bought a sparkly dress by Rizzo. It’s for a photo with my sorority sisters in celebration of membership anniversary.

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Photo: 19-07-22 anabelabelikava AM2 B4
Black Halo Maddox Sheath Dress
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On the one item that gives her the most confidence: When I was younger, I used to reach for my Louis Vuitton Lussac (with matching wallet!) or my Christian Louboutin Maudissima pumps. But they were gifts and I felt inauthentic in them — it wasn’t something I thought I could afford. Now that I’m making more money, I’d rather donate to nonprofits or invest it instead of buying luxury accessories.

I think the most impressive thing I can wear isn’t an item of clothing or an accessory but my smile. It sounds trite, but it’s true. I love fashion and I love looking pulled together. But I think I can still be stylish and impressive even if I don’t have the most expensive shoes, bag, or piece of jewelry. If I show up wearing my smile and being true to who I am, I’m hopeful that my inner light will impress people.

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How to Dress for Work When You’re Always Traveling