A Downtown Date

To galavant around the city and its museums, dark pubs, shops, and fine dining establishments, you need to dress for the possibility of anything, which admittedly, can be hard to accomplish. The foundation of this look is a pair of cuffed jeans, graphic tee, blazer, and comfy yet chic flats; however, the add ons are what make it go from day to night with ease!

1. Scarf | We are in the Windy City after all and the temperature from waiting on the "L" platform to entering American Apparel or even while walking on different streets can change drastically. 

2. A cross body bag with handles | This allows the ability to passionately talk with your hands about Picasso's paintings and sculptures during your day at the Art Institute, while the handles can be utilized later when you are led to the quiet corner table of a seafood restaurant on the river.

3. Statement Jewelry | Once you have your first glass of wine at Elephant & Castle, it's time to roll up the cuff of your blazer and tuck your hair behind your ears to showcase your bracelets and earrings. Also, consider putting on some lipstick!

H&M blazer (similar here and here), XXI tee (similar here and here), Gap jeans, Steve Madden purse (similar), vintage bracelets and ring, leopard loafers, purple scarf, Stella & Dot earrings

"Sunglasses Are Better Than a Facelift"

I always have a blast with my pal Mary. At 71 years old she knows the secret to fooling mother nature, she says, "Sunglasses are better than a facelift, they hide the ravages of time, and let you spy on people." Mary keeps her style chic and classic, but when it comes to glasses she says,"You can break the rules once in a while, I'm not ready for a convent or anything so I can wear leopard glasses." Check out some more of Mary's many shades below.

Madison Chic

I met this chic woman while walking down Madison Avenue. She told me that she has had her camel coat for years and that it is one of her favorites. Is there a favorite item of clothing that you have held onto for years?

Winter Blues

I was delighted to see this gentleman just I stopped off the Subway platform at Roosevelt Island. I photographed him last September, in a similarly colorful orange suit. He told me, " The young men, don't do what I do" and that he dresses up everyday and matches everything down to his socks and shoes. He has been doing this for over 35 years and has been featured in Esquire magazine. I took a small video of him above, and even though it is hard to hear what he is saying, you can sense the joy he takes in dressing from his great smile and charm.

Also Check out this Q&A I did with Forbes for some insight on why I started Advanced Style. CLICK HERE