Redeye Blogs

Wingman Chicago: The November of Dressing Nicely is back.

Let’s get the mood right. Press play and let it ride while you read.

The November of Dressing Nicely is almost upon us, and Chicago gents, it’s time to get your sh*t together.

If this is your first time hearing about this, here’s a little backstory: Last year, a guy from LA came into the office last year to take some meetings with my bosses. He was the best-dressed dude I’ve seen in years.

Upon seeing him, the women in my office had a response similar to this:










Upon finding out the dude was from LA, a co-worker stated, “Oh of course, no guy who lives in Chicago would look like that.” The basic emphasis was: Guys in Chicago usually don’t care what they look like.

So I did. Every single day for the month of November, I dressed to my absolute best effort. No hoodies and “it’s Friday, I’m hungover” outfits. And I wasn’t the only one. A large collective of gents joined up. I posted pics everyday in a gallery for the work blog and this year we’ll be doing the same. I’ve heard from some interested parties, but I’d like to use this opportunity to call out the rest of you. Do you have more pocket squares than numbers in your phone? Did a street style blogger get hit by a car trying to cross the street to get your pic? Then you belong in this gallery.

Here’s how it works:

Starting Tuesday, November 1st:

  • Dress your ass off every work day.
  • Either take a pic of your ‘fit or have someone take it of you.
  • Send the pic to me via e-mail with your name/age by 3pm each day. (You can include details of brands/labels, but it’s not necessary)
  • Act humble when people tell you how good you look in the gallery.
  • Repeat.

You don’t have to participate the whole month, but this year I’m locking down prizes for the gents who go the whole time. If you’re a little hesitant about your style, start here. Follow those rules and you’ll be amazing, no BS.

ALSO: Thanks to the sexy folks at Jbar, we’re partnering up for a #NoDNlaunch party/no real reason other than to do it soiree jawn on Friday November 4th from 9-11. Come say hey.