Using social media, art, and creativity to lift us all up

During times like these we look for ways to take our minds off the crisis at hand, and use humor to lift each other up. Keith Stryker, a long-time supporter of TPAN (the publisher of Positively Aware) and its largest fundraiser the Ride For AIDS/Ride For Life Chicago, got together with a group of friends to create the DailyLookChallenge. We asked Keith and company to tell us what it’s all about.

Jeff Berry: What is #DailyLookChallenge?

Keith Stryker: DailyLookChallenge is a daily opportunity to escape the tragedy that's befallen the world, and feel a bit of whimsy and creativity. A daily look challenge is chosen by the previous day's winner and participants upload their look to Instagram tagged @DailyLookChallenge

JB: How did it come about? Who is involved? Where did you get the idea?

KS: My chosen family has a group text chat. One of the guys, Tom Slazinski, suggested the second day of the stay-at-home order [in Illinois] that we have a daily look challenge among ourselves and we'd vote on the winner. Our first one was private, just the crew, "Crazy Houseplant Goddess.”I posted the photos on Facebook, and Harry Cross suggested we take this public since so many people expressed a desire to participate. We saw a need for distraction, connection, and creativity, so Leo created the Instagram page. The rest of us have been involved in submitting photos, uploading pics, and voting on the winner.

These guys make this happen:

  • Harry Cross
  • Chris Rosario
  • Leo Mikulich
  • Keith Stryker
  • Adam November
  • Zach Fietsch
  • Josh Lubin
  • Rich Rivera
  • Jeff Carroll
  • Evan Rhodus
  • Tom Slazinski
  • Justin Lee
  • Johnny Perez
  • Ryan Bowman
  • Nathan Brown
  • Warren Bell
  • Denn Bod


JB: How does it work? How do you come up with the themes?  

The winner of the day chooses the theme for the next day. All the photos are posted and the theme for that day is uploaded. Submissions are tagged on Instagram @DailyLookChallenge. At 10 p.m. [Central Time] that night we vote via WhatsApp and declare a winner.

JB: Who is it for? What does it do, or what is the purpose?

This is for everyone. We originally started this as something we could do to occupy our stay-at-home time. We love to turn “lqqks” and it seemed like a perfect opportunity to do virtual runways individually from our homes. Since we opened it up for everyone, I get messages every day from people thanking us for doing this as it’s one of the highlights of their day in such a dark time. It's all about bringing joy, laughter, happiness. If I have to be the brunt of the joke to get a laugh, I'm happy to do it. On a personal and maybe selfish level, this gives me 2–3 hours of occupied time, fun time, every day that I'm unemployed and quarantined. I've explored my creative side like I haven't in years, and it feels really good. 

JB: Can anyone play? Are there other groups like this that you know of?

Yes, this is open for anyone to participate. Post your looks to Instagram @DailyLookChallenge for the daily theme.

JB: Anything else you’d like to add?

I'm overwhelmed with gratitude for the people participating. There are amazing entries every single day. I feel connected to my friends that I'm not able to see. And I know on some level we are bringing a ray of light into people's lives through our silliness. 

These have been some of the challenge themes:

  • Crazy House Plant Goddess
  • Spice
  • Home Workout
  • READing is FUNdamental
  • Blossoming Beauties
  • Rhythm & Flow
  • Step Dad Vibes
  • Hunger Games
  • '80s
  • A Day at The Beach
  • Tiger King
  • Boots on the Ground
  • Haunting
  • Heroes & Villains
  • Cocktails & Togas
  • DMT Visions
  • Hippie Love
  • Prom

Some of our favorite participants:

Shawn Watson

Shawn has participated in nearly every one of our daily challenges and he's won twice. He lives here in Chicago. This is what he has to say about it: "The DailyLookChallenge has been an awesome creative outlet that I look forward to each day. Being unemployed from the arts industry right now, this has given me an alternative way to connect with my students, friends, and family."

Shayla Brown

Shayla has also participated in nearly all the challenges. She lives in South Bend, Indiana. “As a stylist and makeup artist (who in the current crisis cannot safely and legally continue my work), the DailyLookChallenge has been a great way to stay active and creative in my field of work while also putting something out there that’s fun and positive. I’ve had so many reach out and say they look forward to seeing the looks, as well as being in closer contact with other friends doing the challenge, so it’s been a great way to stay connected while practicing social distancing.”

Jason Brouseau

Jason, from Chicago, is a regular contributor and his enthusiasm is contagious. He's won one of the competitions but is a regular second-placer. “Some friends and family have checked in on me because they think I’ve lost it. But mostly I hear from people I haven’t spoken to in a while that tell me how much they look forward to seeing our looks every night!”

Tyler Dean

"It's hard to even want to get out of bed during all this, and we have been giving people something to look forward to to cheer themselves and us up." 

Visit where you can see all the entries.

Participant Adam November explains how it works:

We started an Instagram account (@dailylookchallenge) and anyone can enter by hashtagging their photo in the daily theme, and submitting it before 10 p.m. Central Time. (We have been liberal with the deadline and are not going to disqualify anyone.) We were going to have it be an Instagram poll to decide the winner or base it on likes but honestly didn't want it to become a popularity contest based on the number of followers. So, we determined that we would just judge the entries and come to a consensus on who best interpreted the theme. I think we're looking for story, art, and creativity, and I hope that is who the winners represent. It is very difficult, honestly, to judge because people are being really creative and though this is not a serious endeavor at all, there is often fierce competition to pick a winner.

The winner picks the theme for the following day. Tyler Dean, Shawn Watson, Shayla Abernathe, Keith Stryker, and Jason Brusseau have all brought brilliant ideas to the themes. There is a Hunger Games theme photo of two people not from Chicago where they used a MacDonald's Happy Meal box and a bag to make a look that was phenomenal. Keith Stryker as Tiger King and blossoming beauty is great. Shay in horror and at the beach one are fantastic. Jason in Step Dad too. Shawn has had so many good ones, Hunger Games and A Day at the Beach. He also did a story for Prom where he had cards that asked Keith Stryker to go with him that was adorable.

I think my favorite picture is from Johnny Perez, in the READing is FUNdamental category where he's holding a copy of “And the Band Played On” and he’s looking at a wall where "I will wash my hands" is written repeating. I thought it was so timely and brilliant and artistic too.

Thanks for being interested in our little diversion. We were just trying to add some joy and light during this otherwise dark time.

See related article "Love The One You're With: Sex and Pleasure in the Time of COVID-19"

Also see SARS-COV-2 and COVID-19 update for PLHIV