Chicago Style Inspiration

Chicago
[shi-kah-goh, -kaw-]/ ʃɪˈkɑ goʊ, -ˈkɔ- /; a city in NE Illinois, on Lake Michigan: second largest city in the U.S.

I've been fortunate enough to visit Chicago—aka the Windy City—in every season. Each one is beautiful in its own right, even if it can be bitterly cold! But what do you do when you visit in early March and manage to see all four seasons in one week (think sun, snow, hail, and rain)?

You pack wisely.

On this occasion, "wisely" meant lots of layering: sweaters, tees, and shirts that could be easily styled under jackets and warm coats. I even layered my outerwear, using a warm gilet and scarves as extra protection against the elements when needed.

The Strategy: Mix, Match and Repeat
I kept it simple with my choice of bottoms, tops, and color palette, ensuring I could mix and match as much as possible. This allowed me to create several different looks without overpacking (something I find a challenge on most of my travels... I’m learning!).

Of course, I packed the essentials: comfy sneakers for lots of walking, plus leggings and sweaters for morning coffee runs or hitting the gym.

• Outerwear: Relaxed vegan leather bomber, Shearling leather aviator coat, and an oversized hooded & padded gilet.
• Bottoms: Distressed barrel & straight-leg jeans, and relaxed fit barrel pants.
• The Basics: White classic cropped short & plain colored t-shirts.
• Footwear: Kitten heel boots, sneakers, and leather loafers to cover everything from long walks to fun dinners & drinks.

Below are some outfits I styled and loved. I packed a couple of my favorite scarves, they are so light to pack and extremely versatile, to change up almost any outfit. You'll see Anine Bing and Free People jeans make regular appearances; these are such staples for me, I know how to easily style these well for any occasion, dressed up or down. Denim is always the obvious choice for a Chicago city break!