In my process of rethinking shoes that are super handsome, last a lifetime, remain impervious to trends and don’t break the bank, I invested in a smart and classic pair of wing tips with a Goodyear welt from J.Crew (Preston Wing Tips) for $225. They were on on sale for $180 when I bought them. They’re beautifully constructed, and I couldn’t be happier with them.

To accommodate my interest in wearing wing tips all the time, I needed an alternate pair, since one shouldn’t wear the same pair of leather shoes two days in a row. (One should keep cedar shoe trees in them and let them dry for a day.) After some online investigation of the kickers at Florsheim, an old-school American shoe maker and my dad’s shoe of choice, I fell in lust with the Kenmoor long wing tip from Florsheim’s Imperial collection. Like the J.Crew wing tips, they boast solid construction, a Goodyear welt and a breezy $225 price tag.

This afternoon, I decided to march over to Florsheim at Madison & 50th to check them out in person. Not only did they look great and fit like a glove, they were 25% off, i.e. $165. Sold.

With proper investigation and research, I scored two pairs of classic, handsome, sturdy and beautifully constructed wing tips for less than $400 total. Nice.

Read a post I wrote earlier about the Kenmoor Long Wing Tip.

3 Comments

  1. Dennis Lindgren

    Yes sir, long tips are sleek shoes and no doubt about it. Whether you’re a trendy guy or a traditional dresser like me you put on a pair and you look like you know what’s going on. Stout, they provide a great foundation for good posture and carriage. I’ve worn them for decades and own them in several colors and leathers from various shoemakers. Googling long tips led me to your site which I decided to add to my favorites. Nicely done sir.

  2. Hey George,

    Cool post. I just ordered my first pair of Imperials as well. The Chatoms, I believe (needed a pair of black shoes).

    I’ll let you know how they look/feel!

    -Brock