Up for debate: shorts with those shoes?

summertime shoe game

By Megan Collins | Last Updated: Mar 11 2018

{your Style Girlfriend: subway stalker}

Tell me: What do you think of these shoes with those shorts?

I spotted this guy waiting for the L train at Union Square the other day and snuck up behind him evil villain-style to capture his tank top/cuffed shorts/desert boots look. I was all set to post it as a hazard warning – ‘desert boots are not meant to be worn with shorts, people!’ – but then a funny thing happened. The more I looked at the picture on my phone, the more it…didn’t bother me anymore. Putting aside the issue of the tank top, I’m starting to appreciate this hipster kid’s style.

On the one hand:
  • On a purely functional level, tall shoes in the summer seems illogical – aren’t his ankles hot?
  • The visual line is interrupted by the awkward length of the desert boot, making the leg look shorter.
  • It looks sort of like a mistake – l-i-i-i-ike maybe he just couldn’t find his chucks that morning when getting dressed?
On the other:
  • I suppose a desert boot is no different than a high-top sneaker, and those don’t cause such an adverse reaction from me when I see them worn with shorts.
  • I noticed him, and am still thinking about his outfit a few days later. Is that such a bad thing?
  • It’s definitely different, and probably took some thought on his part (I doubt a guy would throw on this outfit and run out the door just because each item was on hand), so I appreciate the effort he put in, even if the overall look is a little hipster for my taste.

What say you? Desert boots (or chukkas) with shorts? Yay or nay?

UPDATE: The “Yays” have it! Bleacherbummed, gentlemanfame and AprailleClarisse liked this guy’s look. Kendrick from A Distinctive Taste seconded the motion, wisely noting, “There are knowing the rules and then knowing which rules to break.”

Glad I wasn’t alone in this!