The old Esquire Theatre still holds down the middle of the Oak Street block at 58 E. Oak, between the boutiques. It has kept its name and its presence on the block for decades, but not its tenants. The theater opened in 1938 and closed in 2006, and since then the building has housed two restaurants. Both are gone, and the second served its last meal on July 17, 2023, according to Eater Chicago.
A third tenant is now getting the building ready, and its plan differs from the last two in one clear way. The earlier tenants treated the space as one large dining room. Esquire, from MStreet Collective, divides it into a main dining room, private dining rooms, a second-floor members' club, and a 12-seat omakase counter inside that club. If you've walked past the dark marquee for three years, that's the real news here.
Two tenants, one large room
Here's how the building has been used since the projector shut off:
| Years | Occupant | How it ended |
|---|---|---|
| 1938 to 2006 | Esquire Theatre | Closed in 2006 |
| 2012 to 2017 | Del Frisco's Double Eagle Steak House, with Esquire Champagne Room upstairs from 2017 | Left the Gold Coast in 2017 |
| November 2019 to July 2023 | Esquire by Cooper's Hawk | Closed, citing underperformance |
| 2026 | Esquire by MStreet Collective | Announced for late fall |
The two restaurant tenants had something in common. Eater wrote that Del Frisco's and Cooper's Hawk were both national or regional chains hoping a Gold Coast address would raise their brands' profile. Cooper's Hawk, the wine-focused chain based in Downers Grove, opened its only Chicago location there in November 2019, partly to give its wine club members, tourists especially, a downtown destination.
The building's size is the detail that matters most. As Eater retold it, founder Tim McEnery told Crain's that tourists did come, but not enough to carry a 24,000-square-foot space. When Cooper's Hawk announced the closing, Eater saw "no indication that a party is waiting in the wings to take over the Esquire spot." That took almost three years.
What MStreet is building inside
Crain's Chicago Business broke the news on May 29, 2026, calling the new steakhouse the third restaurant on the site in less than 15 years. The MStreet Collective announcement released the same day describes a building with several distinct parts:
- Esquire, the main restaurant. 265 seats, with a menu "guided by Japanese precision and grounded in French foundation." The Wagyu program comes from Japan, Australia, New Zealand and the U.S., and the seafood, sushi and caviar menu relies on fish aging. Lighter options are on the menu too.
- A retractable glass front. Lounge seating runs along a wall of glass that opens onto Oak Street, so the building will look out at the block instead of turning its back on it.
- Private dining rooms. The release describes multiple rooms for smaller or celebratory dinners.
- The Trophy Room. A lounge for rare American, Scotch and Japanese whiskies, French cognacs and tequilas, plus barrel-aged Old Fashioneds and freezer martinis served tableside.
- 58 Club. A members' club on the second floor overlooking Oak Street, where membership is by invitation from its founding members.
- ŌakSho. A 12-seat omakase counter tucked inside the club. It serves 16 courses for $285, with two seatings a night, five nights a week, and only limited seats for non-members.
One piece of the last tenancy is staying. The four-level wine tower holds 5,000 bottles, and Eater Chicago notes it was left by Esquire by Cooper's Hawk. The list will be strongest in Burgundy and Bordeaux, with Coravin pours by the glass and a long sake list to match the Japanese side of the menu.
Earlier tenants had to fill one huge room every night. This plan breaks the building into spaces that work at different sizes, from a 12-seat counter to a club that fills by invitation to a 265-seat dining room.
An operator who lives here
The other change is who runs it. MStreet Collective is the design, branding and management arm of MStreet Nashville, led by founder and CEO Chris Hyndman. The Nashville restaurants are Virago, Moto Cucina + Enoteca, Kayne Prime and Saint Añejo, all on McGavock Street in the Gulch. Esquire will be the group's first Chicago restaurant, and the announcement says Hyndman lives in Chicago with his wife, Celine, and is running the project from here.
His statement in the announcement speaks directly to the building's history:
"Esquire was conceived specifically for this historic building on this prestigious block - not adapted to it."
Both earlier tenants brought an established concept to Oak Street and fit it into the theater. Hyndman's pitch is that this concept started with the building, down to the name and the Golden Age of Hollywood look, with custom lighting and sculptural details that call back to the cinema years.
Where the opening date stands
The schedule has already slipped once. The rendering caption in Crain's May coverage said the restaurant would open later that summer. By September 11, Eater's fall preview listed it as "Late-Fall." As of late October, the official Esquire site still says "Coming Soon 2026" and offers inquiry and careers links but no reservations.
That leaves November and December as the realistic window for the fall target, right as Oak Street heads into its busiest shopping weeks. Watch the reservation link on the site. ŌakSho will be the tightest booking in the building for anyone outside the club.
The rest of the block is changing too
Esquire isn't the only change on the corridor this season. The other arrivals help show why the Oak and Rush blocks keep drawing first locations, and why one of them is already open:
- Carmine's, 1037 N. Rush St. This is the one you can visit now. Rosebud Restaurant Group's Italian American standby reopened Monday, January 19, after a $4 million renovation and a three-year closure, Eater reported, citing Block Club Chicago. It has the same menu and stiff cocktails in a sleeker room, with an all-seasons patio that should get plenty of use through the winter.
- Meta Lab, 932 N. Rush St. Meta confirmed to Axios Chicago in August that its first Midwest store will take over the former Glossier space. It will sell AI glasses, including the Ray-Ban and Oakley collaborations, plus VR headsets, and Meta said it expected to open "ahead of the holiday shopping season."
- Toteme, 40 E. Oak St. The Swedish fashion brand is opening its first Chicago store on the block, Crain's reported on October 9. No opening date has been announced.
Two of those three are first-in-market stores, and that's the same pull that brought the national chains to the Esquire building. Oak Street has never had trouble attracting brands that want a flagship address. The theater's track record shows that the hard part is staying, and MStreet is betting that smaller rooms and a club will keep 58 E. Oak busy after the novelty wears off.
Until the marquee lights back up, Carmine's patio is the newest table on this stretch with a confirmed open door, and Esquire's reservation page is the one to keep checking.
Curious what Oak Street's next chapter means for the Gold Coast buildings around it, or want to talk through life a few blocks from the Esquire marquee? Meghan Provenzano Group is happy to walk the block with you. Get in Touch.
