Like so many celebrities before her, Whitney Port (The Hills, The City) jumped the TV personality ship to try her hand at designing clothes. Her line, Whitney Eve, launched in 2009, and owes its bicoastal sensibilities to the fact that Port was born in Los Angeles and has lived extensively in Manhattan. Whitney Eve is surprisingly cool, free from the saccharine, cutesy aesthetic that characterizes so many ill-fated celebrity ventures into fashion. The line is filled with innovative shapes, such as extra-boxy dresses or t-shirts with huge, scimitar-shaped slashes cut from the neckline, and gets its refreshingly quirky edge from pieces like a cropped hoodie with metallic sleeves, quilted white sweatpants, and a sweatshirt printed with a weird-looking owl.

Port is throwing Whitney Eve's first-ever pop-up shop at the Thompson Chicago hotel on October 11-12 to showcase the Fall 2014 line. Port herself will be on hand to greet fans and chat about the fall collection (the event is open to the public, but guests should reserve a spot by emailing info@whitneyeve.com). Naturally, the presence of Port in the city raises several pressing questions: Why'd this bicoastal girl choose Chicago for her first pop-up? Will any of these pieces stand up against Chicago's next snowpocalypse? And who is the line really designed for? I asked Port about the new line and why she's coming here for the shop.

What's your favorite piece in the Whitney Eve Fall 2014 collection?

The Temecula dress! It's an oversized sweater dress that is super cozy, but also really cool. It's really versatile and can be worn with leggings or even a bare leg and booties.

Favorite part of designing clothes?

I love the creative process and envisioning girls in my clothes, but the best part is actually seeing girls in my clothes! It makes all the hard work worthwhile.

Favorite trend for Fall 2014?

Oversize sweaters. A must-have, no matter where you live.

Favorite way to dress for bitter cold weather, like our infamous Chicago winters?

Chicago weather is so unpredictable that it's always nice to layer up. When I’m visiting, I love to wear pieces like thick socks with booties, wool trousers, long-sleeved wool sweaters, cargo jackets, and a beanie.

Favorite dream celebrity to wear/represent your clothing line?

Beyonce, hands down.

Favorite piece of clothing in your personal wardrobe?

My old Burberry Moto leather jacket. I wear it all the time.

Favorite makeup trick?

For a dewy, light glow, I mix tinted moisturizer with regular moisturizer. It gives just the right amount of coverage.

Favorite source of design inspiration?

I look to nature, Pinterest, and the girls in my life to influence my designs.

Why did you choose Chicago for this pop-up shop?

I thought Chicago was the perfect mix of a laid back atmosphere with a fashion edge! My sister also lives in Chicago and knew it would be a fun home to launch the Whitney Eve Pop-Up in. We wanted an atmosphere that girls would feel comfortable in, but one that also reflected the style of Whitney Eve, which is why we decided to hold the pop-up at Thompson Chicago. The design of the property is absolutely amazing and really vibes well with my line.