WHAT TO WEAR: Day To Night

Walking around downtown Chicago might as well be a quasi-runway debut. Not only are there hundreds of stores that offer the most fashion forward and daring trends, but the people of Chicago always look put together and ready for the city bustle. There are so many summer styles to gain inspiration from, which makes my job as a Style Guru hard to choose just one to feature!

Spotting this Fashionisto as he casually gazes at his phone, his leisurely ensemble complete with monochromatic basics and leather accents reminded me of characters that adopted a similar look in movies—think Johnny Strabler in The Wild One (if there are any Marlon Brando fans out there) or the famous T-bird, Danny Zuko. This look maintains an effortlessly cool and suave persona, giving this Fashionisto a nonchalant and confident presence. I especially like how he kept the overall look simple with light washed-out jeans and a blue V-neck that matches the distressed jean material. The brown leather shoes added a hint of color variation from the dark leather jacket, while still maintaining a consistent texture.

This style is the ideal combination for a day to night look in the city. The jeans and T-shirt give a casual vibe and are perfect for running around downtown or catching the latest events and wonders of Chicago. The leather pieces reinvent the casual look to become appropriate for night wear when the temperature drops and the need for a formal look arises as the sun sets and the evening begins. You could even swap out the distressed jeans with a darker wash and add a patterned collared shirt over the V-neck to give the look extra detail for the evening.

To translate this look into a feminine style, I would pair a tight-fitted leather jacket with a simple black tank top and a wrapped mini skirt. Throw on some ankle boots and the day is all yours!

One Simple Change: Let’s say you’re going to run some errands, so what can you wear to still look stylish, yet be comfy? Exchange the leather shoes for some Converse sneakers and you are all set to go!