In the meantime, retailers that seize on Boss' ideal trifecta — convenience, value, and innovation — have emerged as winners, namely the off-price, dollar store, and athletic sectors.
"I think there's real opportunity to own retail here, you just still need to be selective," Boss said. "You look at the off-price sector. The world is coming to them."
Boss' top picks in the off-price category are TJX Companies, Burlington, and smaller-cap name Ollie's Bargain Outlet.
"I think Burlington has the opportunity to double their margins [and] double their store count, so we really like Burlington," the analyst said.
And although Boss has routinely been one of the most negative on Wall Street about The Gap and its subsidiaries, his Thursday note suggested otherwise.
"We're seeing Old Navy solidify. That's half of the story here. So last quarter you saw Old Navy really outpace the retail sector. I think you're going to see the same thing this quarter," Boss said.
Boss added that weather analytics company Weather Trends International is forecasting a "perfect back-to-school setup" in the fall and a colder November, which could mean better holiday sales.
"The Gap Stores is not going to be a name that I'd want on the short side heading into a setup like that," Boss told Cramer.
At the end of the day, analysts cannot deny that retailers are struggling. But when the self-admitted "most negative guy" in the space sees the negativity plateauing, it could be time to seek buying opportunities as a trough approaches.
"I think we're just at the tip of the iceberg of people starting to focus on that, where you think about the market share opportunity for the long term survivors," Boss said. "I think if we've hit that peak, these closures will continue, but the real key is, how many year-over-year?"
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