
Cole Haan Dennehy Loafers
by Cole Haan
1 endorsements on r/BuyItForLife first recommended in Jun 2025
Classic Italian-style leather penny loafer from Cole Haan's Dennehy line.
Added Jul 5, 2026, Updated Jul 7, 2026
Why it's buy-it-for-life
Cited as the model reputedly worn by billionaire Michael Bloomberg for ten years, as one of only two pairs of shoes he owns.
What redditors say
Recommended on reddit as recently as June 2025




The billionaire Michael Bloomberg has only two pairs of shoes, and has worn them for ten years. They're reputed to be the Cole Haan "Dennehy" model, a classic Italian leather loafer that costs around $330.