BACK IN 2008, style-conscious men of Portland didn't have it so good. When Jordan Sayler opened the doors to Winn Perry—a gentlemanly establishment selling elegant shirting, proper dress shoes, and most of the accoutrements necessary for a dapper lifestyle—there were few like it. Independent boutiques catering specifically to menfolk at all, in fact, were scarce, something that was widely lamented at the time.

Winn Perry gained a following among men who valued craftsmanship, classic styling, and the "buy less, buy better" credo. Sayler established symbiotic partnerships with local firms like Columbiaknit and Duchess. And then, in early 2011, Sayler shut the store to take a job in merchandising and product development with Schoolhouse Electric.

Luckily there were other avenues opening for Portland's available menswear, most of which were situated in the West End area of downtown. Frances May had established itself as a destination for men alongside its popular womenswear selection, and the Blackbox retail linchpin filled up with menswear-specific shops like Blackbird, Dunderdon, and Tanner Goods. More recently, other shops with a strong men's representation have continued to fill in the area: Steven Alan, Self Edge, Imogene + Willie, Danner, and Poler (making up some of the slack for ones that have since left, especially Blackbird and Dunderdon).

This month, Sayler, along with a new partner, Kurt Foster, is reopening Winn Perry, and appropriately enough, the new store is a stone's throw from those mentioned above. "I think men have more interest in general in taking an opinion in what they're wearing, and being knowledgeable about what they're wearing," Sayler says. "Making this a good corridor for menswear can only help everybody." (Although he notes the primary driver behind the new location is proximity to the city's hotels.)

And while there's a wider variety for male shoppers in Portland than ever before, Sayler says he doesn't feel that anyone's outright replaced Winn Perry, and the reboot will focus on some of what he perceives to still be holes in the market. A major element of that is footwear. Winn Perry maintained a close relationship with New England shoe company Alden, working with them on special editions that appeal to Alden's cult of collectors, something that will now be revisited. Maine's Rancourt shoes will also be prominently featured—another example of Sayler's preference for working with vendors whose factories are located where the company originates.

Overall, Sayler says the new Winn Perry will be a little more casual. "Tailored sportswear" is the term he gives it, and it'll be here before you know it, with a projected opening date of January 14 at the latest. Until then, a hearty "welcome back," WP. Winn Perry, 209 SW 9th,