A shoe surrounded by broken glass on the floor of the store serves as a reminder of the burglary.
Police say around 1:50 a.m., two men somehow pried open the front door Another man was the getaway driver. The burglars potentially used sledgehammers to smash the cases and got away with handbags, which can run anywhere from hundreds to several thousands of dollars each.
The store is located in Chicago's premier shopping area near several high-end stores. Last month, a nearby store on Walton, the American Apparel, was also the scene of a robbery.
It is not exactly the news merchants and residents want to hear during the holiday season.
"I think it is horrible. You can't run a business. We had a wallet stolen in our store," Oak Street merchant Steve Dubey said.
"The area is really going to develop more and more high-end stores, so it think may be that creates a target for some of these burglars, that they are casing these places, particularly around this time of year when they know that they are fully stocked," said Dan Dowell, Gold Coast resident.
The burglary was captured on surveillance cameras. However, the masks prevented police from getting a good description of the burglars, a Jimmy Choo spokesperson said.
Oak Street merchants pay for extra street security during holiday shopping season.
"I want our window displays to look nice but we have to be mindful," Oak Street Council member Liz Kores said.
Working with Chicago police to prevent another store from becoming a target, the Oak Street Council said it may be time for stores to pull their merchandise out of the windows at night, especially as more high end stores move in, such as the newly opened Christian Louboutin store across the street.
Other neighbors said they are on heightened alert, but the owner of a nearby high-end hair and beauty products store says he is not concerned.
"After 32 years of crime-free business, it is a random thing. If they see something expensive in the front window, they are going to try to get it if that is what they want. There's really nothing you can do to prevent it," said Bravco owner Howard Gordon said.
"There are a handful of things that happen in the area that make you concerned -- what your doing and when you're doing it. Do not be out late at night, things like that. It is a little scary," said Kathy Dowell, Gold Coast resident.