"We came into 2016 with a great setup for holiday, we had a disastrous 2015 as we all know about," Boruchow noted on CNBC's "Halftime Report" Thursday afternoon. Easier comps, slimmer inventories, and a relatively healthy consumer made the setup seem advantageous.
"And look, 25 companies have given us their holiday updates and missed," he added.
Furthermore, Boruchow contended that the backdrop for retail moving forward consists of "really choppy" fundamentals. That uncertainty, combined with the possibilities of an imminent border tax could equate to unfavorable results.
"It really makes it difficult for investors to get comfortable on most the space," Boruchow added.
The difficulty, he continued, is that retailers are starting to replace their vernacular from "cyclical" to "secular" and "on a lot of those guys, mainly in the mall, that creates valuations that continue to compress, making investors less comfortable," Boruchow explained.
However, when questioned if the woes currently impacting retail could be the result of seasonality, and thus may see improvement, he acknowledged that while that may be the case, the signs for underperformance are all to familiar.
"Retail underperformed the S&P last year, first time that happened since 2007," Boruchow said. "A lot of the companies that were best of breed in super high quality businesses, which they are, these are organic growth rates the lowest since 2008 and 2009. A lot of the guys are going to take some time to figure it out."
(Separately, Wells Fargo is held in Jim Cramer's charitable trust portfolio Action Alerts PLUS. See all of Cramer's holdings with a free trial.)