Tip Top Tailors was a Canadian menswear clothing retailer founded in Toronto in 1909 by Polish-Jewish immigrant David Dunkelman (1883–1978).

A now landmark building that housed the manufacturing, warehousing, retail and office operations for Tip Top Tailors was built at 637 Lake Shore Boulevard West, Toronto, Ontario.

Jimmy Kay, however, was more interested in buying the Tip Top Tailors chain of stores than the head office building, a proposition the Dunklemans also rejected.

Separately, each side had failed in their bid to acquire Tip Top Tailors, but during the course of lunch they agreed to pool their efforts and offer the Dunklemans the deal they wanted.

[citation needed] Tip Top Tailors was the first example of a rapid turnaround, a company whose former executives offered numerous reasons for its anemic performance, none of which were accepted by Kay or Posluns.

After a decline in its numerous retail enterprises, Dylex Limited sold the Tip Top Tailors chain to Grafton-Fraser Inc. in July 2000.