This is Emily and she was one of the first style outliers I shot for my blog. I first ran into her on Michigan Avenue and since then, I have chased her many times to shoot her awesome outfits. I love the little details of her outfit – they make the entire look more fun and interesting.

I shot this style outlier early September across from Millennium Park on Michigan Avenue. Each of the outfit pieces – from the wing collar pleated shirt, strap sandals to the hairstyle – all work so well together. An effortless and neat look and a perfect way to take your formal tuxedo shirt the casual way!

Sheer fabrics are always great for the summer but I am never sure what to do with them in the fall. While wandering in Wicker Park, I ran into this lovely style outlier and saw how she turned a simple sheer dress into a chic transition outfit with some nice lightweight layering. I really loved how she combined the pieces in warm shades of  brown with the sheer black dress.

What are some of your favorite summer to fall transition outfits?

This street style photograph was originally featured on Refinery29.