Asking an outfit to play double duty, from day to dinner date, is already asking a lot. But to have it play triple duty – travel, work, and then the weekend is quite a feat.
A few weeks ago, I took on this challenge when I headed to Chicago for a conference. I had to pick an outfit that would comfortable enough to sit on an airplane for two hours, remain presentable so I can go straight to the office for work, and then be fashionable enough to go to a networking happy hour right after work.
Voilà.
Styling Tip –
I’m completely in love with this t-shirt dress by Everlane. The weight of the cotton fabric is perfect – not too thin that you can’t wear it to work and not too heavy that’s it’s stiff and suffocating. With its midi length and the side slit, it’s the Goldilocks of t-shirt dresses and it a great piece that will take you from the airport to drinks.
Adding a jacket helps elevate the simple dress and also adds a layer of warmth for the freezing airplane or office. If the black denim jacket feels too casual, I like to pair it with my favorite vegan leather jacket. The studded flats and jewelry add a little edge while still being comfortable enough to last you through the whole day.
