How does a building on Oak Street, which Eater calls Chicago's fanciest street, go through two restaurants in a little over ten years and then sit empty for more than three more?

At 58 E. Oak St., part of the answer is how big the space is. Esquire, a Japanese-influenced steakhouse from M Street Collective, is the next attempt to fill it. This time the plan is shaped around the building itself, and it arrives while the rest of the block is restocking its storefronts.

A Movie Palace That Was Always Big

The Esquire Theatre opened on February 16, 1938, with Jeanette MacDonald in "The Firefly." William L. Pereira designed it in the Streamline Moderne style, and its single auditorium held more than 1,400 seats. The building was cut up into a six-plex in 1988 and reopened in 1990. AMC closed it on September 14, 2006.

In 2011 the interior was gutted and the marquee came down. According to Cinema Treasures, the vertical sign and part of the facade were kept.

The building has hosted two restaurants since then:

Crain's Chicago Business counts the new steakhouse as the third restaurant in the 1930s space in under 15 years.

Two Chains, One Oversized Room

The first two restaurants had something in common. In its 2023 closing report, Eater Chicago said both Del Frisco's and Cooper's Hawk were chains that took the address to raise their brand's profile with a Gold Coast location. Del Frisco's added a bar upstairs, the Esquire Champagne Room, in 2017.

Cooper's Hawk, the Downers Grove wine-focused chain, opened in November 2019 as its only Chicago location. The idea was a downtown destination for wine club members, especially visitors. It brought in celebrity chefs like Tom Colicchio and Tyler Florence for events. As Eater reported, founder Tim McEnery told Crain's that tourists did come, but there weren't enough of them for 24,000 square feet.

For the most recent tenant, the size of the building was part of the explanation for closing.

What Esquire Is Doing Differently With the Space

The new Esquire takes its name from the theater, and the plans in Eater Chicago's fall preview read like a response to the building's history.

1. Several floors, with a private club inside. Eater describes a multi-level, 265-seat restaurant. It includes ŌakSho, a private club built around a 12-seat omakase. That gives the building both a large dining room and a very small one.
2. A wine tower kept from the last tenant. The multi-story, 5,000-bottle wine tower from Esquire by Cooper's Hawk is staying. Rare and reserve whiskies and a long sake list are planned alongside it.
3. A menu built around wagyu and aged fish. The plans include a wagyu program, plus sushi, caviar, and seafood prepared with fish-aging techniques.
4. A design nod to old Hollywood. Custom lighting and sculptural elements draw on Hollywood's Golden Age, which fits a building that started as a 1938 movie house.
5. A window onto Oak Street. A retractable glass window will overlook Oak Street.

The previous tenants were national chains opening one showcase location. Esquire is a single concept planned for this specific address. The 12-seat room shows the thinking most clearly, since it's a table the building can fill on a quiet weeknight.

The timing has moved back. In May, Crain's said the restaurant would open "later this summer." Eater's September 11 preview gave a "late-fall" estimate. The restaurant's website still reads "Coming Soon 2026." It has links for inquiries, careers, and Instagram, but no reservations yet.

The Block Esquire Is Opening Into

The last time this building changed tenants, Esquire by Cooper's Hawk was the big new arrival on Oak Street. The new Esquire will join a block that has added several new tenants in 2026, all within a short walk.

ARLA, 15 E. Oak St. Hospitality Included opened this Mediterranean-Japanese rooftop restaurant on June 18, on the sixth floor of the former Fred's at Barneys New York. Chef-partner Soo Ahn, who is also behind Adalina Prime in the West Loop, built a menu with dishes like a caviar sando on shokupan, charred scallion pita with burnt dashi butter, and whole cauliflower roasted over live fire. Block Club Chicago reported that the two terraces seat 60 together. One sits at the corner of Oak and Rush, and the other overlooks Mariano Park.

Toteme, 40 E. Oak St. The Stockholm fashion brand leased ground-floor space in the 20-story apartment building at 40 E. Oak for its first Chicago store. The Real Deal reported in early October that build-out was set to begin the following week. No opening date has been announced. Golden Goose, which recently redesigned its storefront, shares the building's ground floor.

Christofle, now at the Drake Hotel. The silverware boutique that used to be at 40 E. Oak hasn't left the area. It moved into ground-floor retail at the Drake.

Meta Lab, 932 N. Rush St. Around the corner, in the former Glossier storefront, Meta confirmed to Axios Chicago that it is opening its first Midwest Meta Lab. These stores let shoppers try the company's AI glasses, including its Ray-Ban and Oakley collaborations, along with its VR headsets. Meta VP Matt Jacobson told Axios the company expects to open "ahead of the holiday shopping season."

Taken together, the block already has a rooftop dining room at 15 E. Oak, with a new fashion store coming at 40 E. Oak, a tech showroom coming around the corner on Rush, and the theater building at 58 E. Oak preparing to reopen. Cooper's Hawk was counting on visitors in 2019. Esquire is opening on a block that now gives people several different reasons to come.

Walking the Block This November

Here's what you can see on a walk from Michigan Avenue toward Rush:

• 58 E. Oak: The former theater, with the restaurant still marked "coming soon" on its website.
• 40 E. Oak: Toteme's build-out, next to Golden Goose. The building owner, Berger Realty Group, recently upgraded the stone facade, front doors, and canopy, according to The Real Deal.
• 15 E. Oak: ARLA, six floors up, with one terrace at the corner of Oak and Rush and another overlooking Mariano Park.
• 932 N. Rush: The former Glossier storefront, being turned into Meta Lab.

Esquire's own announcement will most likely come through its website and the Instagram account linked there. When it opens, the 1938 building will have its third restaurant in under 15 years, this one planned around the size of the space.

Buildings like the Esquire are part of the Gold Coast's architectural history, and we pay close attention to how blocks like Oak Street change from one year to the next. If you're thinking about what this stretch of the neighborhood means for your own home, Gillman Group is happy to walk it with you. Let's Connect.