Midwest Express

A menswear show, tavern style pizza and one of the truly great American shops. Two quick days in Chicago and Cleveland.

Looking forward to a mid-winter adventure to Illinois and Ohio could classify me a rare breed of traveler, but I do love the midwest in the winter. My residence in Los Angeles with no real weather is likely to blame. No one wants to hear about missed seasons, but I do long for a bit of winter. Not blue-bird Colorado winter (which is good in its own rite), but overcast, freezing rain, level 3 seat-warmer winter — which of course is the specialty of the midwest.

I visited Chicago recently to survey the menswear landscape that is the Chicago Collective menswear trade show. After Chicago I went to Cleveland for one day to see my mother and of course make the pilgrimage to Cuffs Clothing in Chagrin Falls, one of the truly great stores in America.

My recap from Chicago this year is slightly more muted than last time (that story was one of the most popular in the ACL Substack era). That post probably resonated because I used to go to trade shows and recap them in a similar way. It’s hard to look at things with fresh eyes each year, and going to Chicago last year just felt fresh. This year it was less new, but still very solid. Someone at the show commented that “this is where stores go to buy clothes which people actually wear,” which I thought was an appropriate summation. If you shop at good men’s shops then this is where those people go to buy.

Cuffs Clothing in quaint Chagrin Falls, Ohio.

Cuffs owner and patriarch Rodger Kowall. This man is truly visionary and if you every can make the journey to Cuffs to buy a suit or just drink wine I promise you it will be worth it.