Sketching People Challenge (Day 1 to 11 of 365)

Two pencil blind contour portraits with watercolour added. One man with crazy teeth and hair. One lady with sunglasses and teeth with braces.
Blind Contour Portraits

My first #Kick365 Day Challenge of Sketching People

I didn’t track my sketches for this challenge as I was doing them, so I figured it was going to be easier to go through my Facebook posts on Kick in the Creatives, than trying to go through all my sketchbooks to track down the original sketches.

Why I did this 365 day sketch challenge

The reason I want to commit to a year of sketching people is to explore different sketching styles. I want to find a sketching style that feels the most natural. I also want to develop stronger technical drawing skills for sketching people, especially perspectives and accurate proportions. But, most importantly, I want to play. It’s through experimentation that we can really appreciate the value of getting lost in art. It’s not about the results, it’s about the journey. Welcome Aboard!

My Blind Contour Process

I thought that by doing blind contour sketches to begin this year-long challenge, it would be a good way to be playful and loosen up. And not take sketching too seriously.

My approach to blind contour is:

  • Sketch a simple blind contour sketch using a pencil.
  • Add additional details while looking at the sketch
  • Add watercolour

In many of these sketches I drew simple mouths, but then added some wild and wonderful teeth! It’s this ability to add an injection of imagination into the second sketching stage that can really deliver a sense of playfulness into the final portraits.

Having Fun. And Learning. A winning combination.

Blind Contour is Good Practice for Urban Sketching

These blind contours (or maybe they’re technically half-blind contours) – are meant to hone your hand eye coordination. It’s a good sketching method for urban sketchers to practice, because when you’re sketching people from life, you have to spend a lot of time looking at the subject your sketching and not at your paper. So the more practice you get at sketching without look, the more confident your urban sketches will be.


Day 1 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#Kick365 Day 1 
 ink and watercolour sketch. blind contour of a women's portrait. sketch stages and a finished watercolour portrait. Lady with glasses and facemask
#kick365 sketching people day 1

Day 2 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#Kick365 Day 2
 ink and watercolour sketch. blind contour woman's portrait in a pink teeshirt and braces on her teeth. Wearing sunglasses. sketch stage and a finished watercolour portrait.
#kick365 sketching people day 2

Day 3 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#Kick365 Day 3
 ink and watercolour sketch. blind contour woman's portrait in a headscarf and sunglasses. sketch stage and a finished watercolour portrait.
#kick365 sketching people day 3

Day 4 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#kick365 sketching people day 4 girl in a blue bottle hat and blue coat. Big Smile. Blind colour sketches and watercolour version.
#kick365 sketching people day 4

Day 5 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#kick365 sketching people day 5. blind contour sketch of a boy with curly hair and glasses. pencil sketch, and finished watercolour portrait.
#kick365 sketching people day 5

Day 6 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#kick365 sketching people day 6. blind contour sketch and watercolour of boy with a purple tee shirt and a big smile.
#kick365 sketching people day 6

Day 7 of #Kick365 Sketching People – Blind Contour Sketch from Photo

Blind contour sketch of girl with the pearl earring.
#KICK365 Day 7 sketching people

Day 8 of #Kick365 Sketching People – Blind Contour Sketch from Photo

#kick365 sketching people day 8 blind contour sketch of a boy with big blue eyes. pencil sketch and a watercolour portrait
#kick365 sketching people day 8

Day 9 of #Kick365 Sketching People – Blind Contour

Continuous Line sketch of a person with a day pack. from the back in ink.
#Kick365 Day 9 Sketching People

Day 10 of #Kick365 Sketching People – Blind Contour

#kick365 sketching people day 10 of a halloween figure with spikey hair. Blind contour pencil sketch and watercolour portrait. Sid Vicious with better teeth
#kick365 sketching people day 10

Day 11 of #Kick365 Sketching People – Blind Contour

#kick365 sketching people day 11. blind contour sketch of a young man in a brown turtle neck sticking his tongue out. pencil sketch and watercolour portrait
#kick365 sketching people day 11

Blind Contours are the gift that keeps on giving. You learn along the way, you hone your sketching skills, and you can have a little fun doing it. What’s not to love.


Author: Roving Jay

Jay is a project manager who swapped corporate life for a nomadic existence as a travel writer and urban sketcher. Jay has published travel guides, nonfiction writing books, and poetry collections.

Leave a Reply