I know… “Florsheim.” But hear me out…

When I hear the name Florsheim, I think of shoes my dad would wear. “Old man-ish,” “conservative,” or “uncool” are some descriptives that come to mind. I wouldn’t consider Florsheim an edgy brand on the “get” list for most hipsters.

But when someone makes a smart and well-crafted long wingtip shoe with a quality leather upper, a leather lining, and a Goodyear Welted double leather sole with nice English “heft” to the thickness and width, I don’t care what the perception of the brand is. Introduced by Florsheim in 1949, the Florsheim Imperial Kenmoor Wingtip is that shoe.

I’m a sucker for a pair of wingtips. Shoes from Alden, Church’s, Grenson and other top-tier shoemakers are glorious, but a pair of them will run you a half a grand or more. Florsheim Imperial Kenmoor Wingtips, on the other hand, will set you back an easy $225. They come in black, burgundy, “tumbled” pebble-grain black, and cognac (pictured below). They’re fabulous shoes.

I have three pairs.


TIP: Florsheims tend to run narrow for my foot. Where a medium D width is my usual, E is actually better for me with the Kenmoor Imperials.


  1. would you recommend these or the J. Crew preston wingtip for a wedding?

    • George

      If you are just attending the wedding, i.e. wearing a suit, these or J.Crew’s Preston Wingtips are great. If you are the groom or a wedding party member, and the dress code is semi-formal, i.e. non-tuxedo suits, the wingtips are perfect. If you are the groom or in the wedding party and wearing a tux, no. Wingtips are semi-formal shoes and not appropriate for wearing with a tuxedo (unless they’re patent leather). You will need what are called “pumps,” which are formal patent leather oxfords for wearing with a tux. (See Florsheim’s “Kingston” formal oxfords.)

  2. How have these held up? I’m interested in buying a pair but am scared of some of the other reviews.

    • George

      Hi, Ronald… They’ve held up very well.

  3. Hi George

    Long time follower of your blog. I have been considering getting these shoes for quite sometime now, but have been getting mixed reviews about their quality.

    I really like the black tumbled pair, which you have I believe. How have they held up? and how often have you worn them? Have they needed resoling at all?

  4. How comfortable is it to walk in these shoes? I tried a pair once and I thought that my knees would wear out prematurely if I wore a shoe like this.

    • George

      Depends on the shoe. I love a substantial sole with a Goodyear welt. All my dress shoes are like these. Some are harder to break in than others. But once you break them in, they’re a loyal comfortable pair of shoes that will last a lifetime.