Dana Weiss is a fashion and celebrity style blogging superstar also known as The Possessionista, (her blog name). Her blog follows the most fashionable shows on television (think Gossip Girl, 90210, Modern Family, Pretty Little Liars etc), then helps readers recreate the looks by tracking pieces down and showcasing them on her site (which she does by having great relationships with the stylists and designers that work on the shows).

We asked Dana to share her secrets for stylish shopping in her hometown of Chicago, in the hope that by following her tips we can be at least a little bit as fashionable as she is…

What are your favorite stores in Chicago?

I love Ikram, Sofia, we have a great TopShop, and I adore All Saints, and I also just love walking Michigan Avenue, even though it is a bit touristy because we have that amazing Nordstroms. I think that there’s a great energy that comes with walking around Chicago on a sunny day that just makes you want to try on clothes! One thing about Chicago is that our stores are really beautiful, you’re not shopping in a closet! There are all these high ceilings, and converted lofts with exposed brick and piping, the whole thing is really cool, it makes shopping in Chicago a great experience.

Are there any great neighborhoods for boutique shopping?

The Uptown Wicker Park area is great around Milwaukee. There are lots of independent stores, for example I love P45, and although the area has been getting more chains opening up there they tend to be more interesting chains like Marc Jacob and Club Monaco.

What are your favorite shoe stores in the city?

For shoes, there’s a store called Shirise that has amazing high-end collections that are so beautiful. I almost never shop there because I can’t afford it but it’s a great store to go in and touch the Chloe boots – it’s a lot of fun! And I love the Barney’s shoe department, that is always awesome. There’s a chain here called Lori’s, which is current lines but heavily discounted, where you can get things like Frye and Steve Madden.

Where are the best places to go to watch fashionable people in Chicago?

The hottest place right now is RPM, which is Juliana and Bill Rancic’s restaurant, and the food is incredible, and the people that go there are beautiful. Just down the street from there is Sunda, an Asian/ Japanese place. Chicago is a beautiful city with beautiful people, and I think a lot of chefs come here to try their new ideas, so we have incredible restaurants.

Do you think that Chicago has its own style esthetic?

I think in a lot of ways we are behind places like New York, but I think Chicago does it best when we stop trying to be LA or New York and accept our natural and beautiful midwestern-ness. New York is all black, LA is all boho, and Chicago has a lot more whimsy, there’s a lot of color here, a lot more patterns. I think that because our winters are so bad and our summers are so good, there are always lots of good sandals and sundresses in our wardrobes.