Oak Street Finally Has Somewhere to Eat. The Address Explains Why.

Walk down Oak Street on a warm evening this summer and something is different from five years ago. The block still reads as the place where you buy the coat, not eat the dinner. Chanel, Cartier, Balenciaga, Van Cleef & Arpels: the storefronts haven't gone anywhere. But look up now, past the awnings, and there's a rooftop terrace with people leaning on a railing with drinks in hand, looking out at Lake Michigan. Look at street level a few doors down, and a building that spent a decade being one thing has just become another.

The two restaurants making noise here this year didn't get built from scratch. Both moved into addresses that something else had just vacated, and the reason so many storefronts on this one block keep changing hands traces back to a single fact about Oak Street real estate: a 2019 sale here still holds the record for the most expensive price per square foot ever paid for a retail property in Chicago. That record valuation is what keeps forcing the turnover that just handed the neighborhood two new places to eat.

The Six Floors Above Cartier

Start at 15 E. Oak St., a building most Chicagoans still think of as Barneys New York. The department store closed here after its 2019 bankruptcy, and the building sat mostly empty until landlord ASB Real Estate Investments rebranded it Oak x Rush and rebuilt it floor by floor. Cartier moved into an 8,000-square-foot boutique on the first and second floors. Balenciaga took a two-level, 6,700-square-foot shop. And the top floor, the space once occupied by Fred's at Barneys, sat empty until this summer.

On June 18, it became ARLA, an 8,500-square-foot Mediterranean-Japanese restaurant from the team behind Adalina and Adalina Prime, under chef-partner Soo Ahn. Floor-to-ceiling windows frame the skyline indoors, and two outdoor terraces add another 60 seats, one facing down Oak Street toward Rush, the other looking out over Mariano Park. Ahn told Block Club Chicago the idea came from a Mediterranean-Asian restaurant he encountered on a trip to Miami, and that he built ARLA to sit comfortably next to Gold Coast institutions like Gibsons, Hugo's Frog Bar, Carmine's, Maple & Ash, and Tavern on Rush rather than compete with them.

"I'm not really trying to compete with anyone."

That's a modest way to describe taking over the top floor of a building that couldn't hold a tenant for years after one of the most storied department store names in American retail walked away from it.

One Address, Three Businesses, Ten Years

A few doors east, at 58 E. Oak St., the turnover runs deeper. This building started as the Esquire Theatre, a movie house that gave the block its name recognition long before the boutiques arrived. When Christian Louboutin wanted a Chicago flagship in 2014, it took over the old theater space, trading film reels for red-soled heels. At some point after that, the address became home to Esquire by Cooper's Hawk, a wine-forward restaurant concept that built a four-level, 5,000-bottle wine tower as its centerpiece.

This year the address changed hands again. MStreet Collective, led by founder Chris Hyndman, unveiled a new restaurant simply called Esquire, a 265-seat Japanese-influenced steakhouse built around a wagyu program, sushi, caviar, and a fish-aging system. The design leans into the building's cinematic history with custom lighting and sculptural details meant to evoke Hollywood's Golden Age, and a retractable glass window will open onto Oak Street itself. Tucked inside will be ŌakSho, a 12-seat private omakase club. The wine tower is staying. Everything built around it is changing.

One storefront. A cinema, a shoe boutique, and two different restaurants, all within about a decade. That's not a coincidence of good timing. That's what happens on a block where the real estate underneath the storefronts keeps changing ownership faster than the businesses inside them can settle in.

Why the Landlords Keep Changing Their Minds

Here's the part that explains the other two. Van Cleef & Arpels is relocating this year from 65 E. Oak St., where it currently sits wedged between Chanel and Moncler, to a newly built-out space at 67 E. Oak St. According to The Real Deal, the move is happening because Van Cleef's current landlord, German institutional investor Union Investment, hired Newmark last October to list the property for sale. Union Investment bought that building in 2019 for $120 million, a price that worked out to more than $4,100 per square foot. As of this February's reporting, that remains the highest price per square foot ever paid for a retail property in Chicago.

A landlord holding a record-setting valuation eventually wants to cash it in, and when they do, even a marquee tenant like Van Cleef has to find a new address. The same pattern shows up a block away. In late 2024, the building at 41 E. Oak St., leased by Bottega Veneta, sold for $17 million to the Maramotti family, the owners of Max Mara. Different building, different tenant, same underlying mechanism: Oak Street real estate is valuable enough that ownership keeps turning over, and every time it does, whatever sits inside gets shaken loose.

Most of the time what moves in next is another fashion house. This year, twice, it was a restaurant instead.

What Changes for Anyone Who Already Lives Here

None of this is about whether to buy on this block. It's about what a Tuesday evening looks like now if you already do. For years, an evening on Oak Street meant browsing until the shops closed and then walking somewhere else, usually Rush Street, for dinner. That's no longer the only option. You can start with a spritz on ARLA's terrace as the sun drops behind the skyline, and once Esquire opens half a block away, close the night under its restored wine tower, all without leaving a stretch of sidewalk shorter than the walk from your building's lobby to the elevator bank.

The shopping hasn't gone anywhere. Van Cleef will still be here, just two doors down from where it used to be. What's changed is that the same forces that keep shuffling the boutiques around this block finally shuffled a couple of restaurants into the mix, and the neighborhood got a genuine reason to stay out past the last store closing.

If you're weighing what a Gold Coast address delivers day to day, beyond the storefronts everyone already recognizes, that's worth knowing before you make any decision about this corridor. RM Luxury Group works with buyers and sellers across Gold Coast, River North, and downtown Chicago's other high-rise neighborhoods, and can walk you through what a block like this one actually offers once you live on it. Reach out to request a private consultation.