Sally Trainor, 23
Student, James Madison University (marketing)

What she’s wearing:
Coat from Wal-Mart (“I get compliments on it all the time!”), American Apparel T-shirt, Urban Outfitters scarf, H&M jeans, Goodwill boots and blue straw bag. The yellow Samsonite bag is also thrift. Her hat is from Urban Outfitters; she made the feather pin herself (“They have ones like it at Urban, but they’re expensive”).

Tell us about your style:
“I wear what I like. I guess my look could be described as bohemian or vintage. I definitely dress differently from the people at JMU.”

And how’s that?
“The girls wear mostly leggings, Uggs, and sweatshirts. So they’re basically wearing sweats, but they have their hair and makeup done. And they wear Chanel jewelry with it. I just don’t understand it! I guess you could call it ‘pajama chic.’ ”

Any tips for looking stylish when it’s so cold out?
“I am a fan of wearing dresses all year long. I wear tights under them, and I sometimes wear tights with shorts. I figure I’ll be inside soon.”

What did you pack for the trip?
“Mostly dresses. This is my first time there without my parents, so I get to do whatever I want. My boyfriend has a friend there, and we’re going to go to bars and go vintage and thrift shopping.”

What’s on your holiday wish list?
“Minnetonka Moccasins—the midcalf boots with the three layers of fringe.”

Rachel says:
Both Sally and I were bound for New York when I took her photo (different Chinatown buses!). When I was there, I noticed tons of young and stylish women wearing these slouchy, knit hats, and I saw at least a handful rocking that shorts-and-tights combo. A note on that: Try this trend only if you’re tall and/or very thin and don’t have to be outside for long!

Weigh in on Sally's style!

What do you think of this week's Sidewalk Style outfit? Tell us your thoughts in the comments!

Earlier:
Sidewalk Style: In Bloom 
Sidewalk Style: One-Name Wonder
All Sidewalk Styles

More>> Shop Around Blog | Style | Find a Spa