My boyfriend and I took our annual summer trip this past weekend, and chose to visit my favorite city. He’d never been before, and I was dying to drag him around and impress him. Beware, this is a long post.

We saw all the sights, and I did so largely in a pair of Bieber pants. I was browsing my favorite consignment shop the day before our trip and came upon these James Perse cargo capri sweats (they’re actually more of a t-shirt type material– not jersey, but old school cotton). They were kind of an inessential purchase (ha) so I decided I needed to make the most of money spent by wearing the hell out of them this trip. Plus, they’re versatile and perfect for pre-fall in the Windy City. Since we were walking around so much, I wore them with sneakers, but they’re great with ankle boots as well.

I didn’t want to bore Chris with too much shopping, so I skipped what’s known as the Magnificent Mile– an expansive downtown stretch of luxury retailers and massive, multi-level stores like Target and Forever 21. Instead, we checked out some of Chicago’s Northside neighborhoods, like Bucktown, a Brooklyn-esque area full of boutiques, consignment, and vintage. I also spent a day with my cousin in Roscoe Village, which ended up being by favorite shopping spot of the weekend. It’s a pretty unassuming neighborhood on first glance, but it was filled with small shops and truly unique finds.

CHICAGO HAUL

I’m a huge sucker for draped, asymmetrical cuts, so I swiped this jacket/sweater hybrid off the mannequin as soon as I saw it. It’s by Blank NYC, and the back and sides are faux leather. Brown jeans are a surprisingly rare find (in my experience), and I love earth tones for fall and winter, so I also jumped on these burnt sienna coated denim pants by Red Engine. I love the print of this super-soft Monrow sweatshirt, which I feel like I’ll be living in once it gets a little colder out. I got all of this and the gold bracelet with inlaid stones at one store, called the Denim Lounge, which basically bankrupted me for the weekend. They were having an incredible 75% off sale on tons of gorgeous stuff. (I could have done a lot more damage if I’d had a couple of beers with my Murphy’s hotdog, and I kind of wish I did.) The delicate stone and spike necklace was from a store across the street, called Hubba Hubba. The sneakers are by a San Francisco brand called Chrome, which makes super durable, masculine shoes and bags (though they do carry women’s sizes in a handful of designs). Chris and I each got a pair on sale at their store in Bucktown.

I guess the only thing that could rival the shopping in Chicago is the food. (And the architecture. And the limitless number of things to do.) But yeah, eating out usually ranks among the highest on my list.

Luckily we were right down town, and were within walking distance of plenty of bars and restaurants. It was a little cooler at night, so I got to break out a couple of warmer pieces.

Coincidentally, our friends Mike and Pearl (of Chandeliers and Ripped Jeans) were in Chicago for the weekend as well. We were lucky enough to catch them one night for a couple of drinks at the Hubbard Inn, a gorgeous, multi-level restaurant bar downtown that had the feel of an old saloon mixed with an artist’s loft. I couldn’t take too many photos because it was so dark, and I didn’t want to disturb everyone with too much flash-photography. But I did get a picture of our lovely and fashionable friends.

On the last day of our trip, we visited the Art Institute for an exhibition on Impressionism, Fashion and Modernity. The show featured works by Impressionist painters like Degas and Manet alongside the actual garments worn by their subjects, housed in glass cases. It was pretty amazing to see them side-by-side. I wish I could illustrate this with pictures, but naturally, photography wasn’t allowed in the exhibition. Suffice it to say, the corsets looked really, alarmingly uncomfortable.

And then we were on our way home. Until next time, Chicago.