Dress Chukka suggestion?

[Bert01]

Hey guys, does anyone have any suggestions for a comfortable pair of dress boots for sidewalk hiking in the city? I wear Carolina loggers everyday for work and have some twisted X moc toe steels for meetings and stuff but I’m not in love with them. My wife likes to travel and I’m looking for a pair of boots that are nice enough to wear out with her but comfortable enough to keep up with her too.

 

[dreamingWest]

I like the Redwing Weekender Chukka for exactly what you describe. Mine are going on 6 years now.

 

[Dos XX]

Redwing, Timberland, Ariat, and Blundstones. I think the Blundstones are the most comfortable to my feet. The Ariats and Timberlands are tied for 2nd. The Ariats win on price.

I don't get along with the Redwings as well for some reason, and they were the most expensive and best looking of all of them.