Dress: J.Crew Maritime Dress ($88)
For Winter. If I had a uniform for casual winter days, this would be it. I like the simplicity of a dress and leggings with boots, but I also like that it’s a bit more dressed up than jeans.
Here, I added a scarf for warmth but also to break up the pattern a bit. You could add a belt–I’d recommend cognac, not black–or achieve the same effect with a few layered, long necklaces. This just helps elongate the body and resist some of the compression that horizontal stripes can cause.
I added this lovely chain strap Tory Burch clutch for color. You could also wear a crossbody satchel or messenger bag.
This is the ideal plane outfit because it’s comfy and warm and you look dressed up enough that getting bumped up to business or first class shouldn’t be a problem. Then again, I’m always amazed what frequent travelers will wear when sitting in first class. The state of America’s travel wardrobe is truly atrocious.
For hair, I’d choose something relazed, either a bouncy ponytail or a natural wave worn down. For the makeup, also choose something more natural. This is a casual outfit so you don’t want to be too made up.
For Spring. I took a page from Bee’s playbook (Altlantic-Pacific) and paired the dress with chambray. She wore it with a knee-length dress which looked lovely, but I think I’d prefer a simple shirt.
To jazz it up a bit, I added a relaxed flat sandal, a beaded necklace and a metallic bag. In real life, I would probably wear more than one necklace, but you get the idea.
If I decided to skip the necklace and opt for a belt, I would choose something a bit rugged and worn in a complimentary shade of warm brown. I’d also pop the collar. Quelle horreur.
I’d also roll the sleeve so that the chambray showed on the outside. I wouldn’t do a bracelet, but you certainly could. I prefer to keep my accessories to one part of the body, so I wouldn’t mix necklaces with bracelets. But that’s just a personal preference.
For the hair, I’d do a wavy, twisted updo. Probably a low bun or a Gibson roll. For the makeup, I would do a punchy pink cheek and berry-tinted lips. I’d also pour on the mascara. When you wear your hair up, I feel like the eyes become twice as important.