In or Out: Working The Sport Boot

Since publishing an entry this past January with an early 70s photograph featuring Paul Newman, a dirt-bike, and a pair of biker-esque boots, I diligently hit internet auctions every morning for seven months to race down, at last, this “near mint” pair of 1960s Red Wing Irish Setter Sport boots.

They differ somewhat from my original inspiration, but they were just the style and color I figured would work with my day-to-day wardrobe. Now that I’ve finally got them, I’ve had to figure out to make them look cool with my pants when I’m not wearing slim 60s denim and sitting on a mini-motorcycle as Mr. Paul Newman was.

First I started with my pants crammed inside, but it takes time and it takes work to get them in there alright, and the resulting look is undefined and essentially dowdy.

Pulling the pants out streamlined the silhouette, but I can only think of electricians and dishwasher delivery men wearing them this way.

Neither in nor out was working, so I finally tried my pants the way I normally wear them, cuffed up twice. So far that gets me and my boots nearest that Newman photograph so I’ll roll along that way and see how often I end up wearing these biker-y boots I spent all year yearning for.

(Slimmer pants will probably help too. I’ve loved these canvas, khaki ones quite a bit, but half a year without fried chicken and chocolate milk and they’re just too big now.)

2 Responses to “In or Out: Working The Sport Boot”

  1. Saucy Says:

    Cuffed with skinnier pants is definitely where I would take these babies.

  2. Damien Says:

    Some would say pants out if you want them to take you seriously but I imagine you may not neccessarily be conerned with all that. I vote for cuffed!