The weather is changing drastically here in Chicago and us Chicagoans already know what’s soon to come, snow. So for me it was important to wear a few of my new pickups and my favorite sneaks before the snow hits the ground because trust me your favorite will be ruined by the salt and nasty slush.

For me it’s all about comfort and avoiding going with the all black demo when it came to styling these. So I decided to throw on my Opening Ceremony t-shirt and a longline varsity jacket from Kendall + Kylie’s second collection with TopShop. We decided to shoot in the super popular Maggie Daley Park which is close to the Millenium Park, The Bean, and other attractions in downtown Chicago such as The Chicago Symphony Orchestra, The Magnificent Mile and more.

I picked up the Opening Ceremony t-shirt in-store while visiting New York this summer for the unveiling of 2016 Olympics uniforms with Nike. Of course this wasn’t on sale but it was worth the splurge of $75 in my opinion and the Opening Ceremony store is amazing! They carry so many different brands from Alexander Wang, Acne Studios, Comme Des Garçon, and more. If you’re going to spend some extra cash then make sure it’s on an item that you really want and not just for the moment! (Rule of thumb: Can I wear this two years from now?) But a simple black tee with a graphic is easy style with different color denim preferably blue or black or shorts if you live in a warm climate. You can even throw on a leather skirt too. So this was definitely a go for me!

I thought I almost missed out on the 'Banned' Air Jordan 1 but luck was on my side almost 3 weeks later!Initially I thought to purchase from a resellar but I just happened to stop in Villa and these were on the shelf and it was sign from above!If you decide to get any pair of Jordan's I would go with a retro Air Jordan 1 because it's a classic and iconic sneaker, you can't do any wrong with this pair. Plus, me being from Chicago and grew up wearing Jordan's it's only right that a pair stays in rotation. You still might be able to grab a pair for a reasonable price! For the exact pair of Air Jordan 1 'Banned' sneaks I'm wearing click here.

Photos: Kyle Goldberg