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Top Designers 2025

James Olstein

Artwork by James Olstein

James Olstein is an illustrator and author from Philadelphia specializing in creating digital art that retains an old-school look and feel. James uses grainy textures and overlapping vibrant colors to give modern subjects an analogue feel. James works in the fields of editorial, brand, packaging, and book illustration. His hobbies include drinking coffee, listening to records, and getting messy from screen printing. Much to the dismay of his neighbors, he also plays the drums. He has never met a donut he didn't like.

Hi James! Tell us about yourself - how did you get to where you are today?

Hello! I got started going to school for graphic design. After many years of working at sandwich shops and grocery stores, I got my first design job as a web designer. After a few years I transitioned into working for ad agencies. In 2012 the agency I worked at was hiring a lot of illustrators for projects and when they needed additional illustrations, I said "I can do that!" I really enjoyed the work and when I saw the difference in my day-to-day compared to the illustrators we hired I decided to make a plan to go freelance. In 2016, I quit my day job and have been doing this ever since.

Portrait of illustrator James Olstein
I'm partial to something that helps tell a story in a clever way or humorous way. I rarely remember really beautiful detailed illustrations compared to more simple bold work with a sense of humor.
James Olstein

When did you first become interested in art and design?

I became interested in art the first time I saw a Spider-Man comic in my local drug store. I was obsessed with trying to copy the art from Spider-Man and Star Wars comics. When I was older I discovered punk music and the DIY aspects of it. After seeing homemade zines and album art I wanted to get into graphic design.

Artwork by James Olstein

How would you describe your design style and how has it changed over time?

I think my work started out pretty basic. It looked like a lot of other illustrators using heavy textures at the time. Although I still use a lot of textures, I've gone for a more comic approach to how I draw people and animals. I was very influenced by the Ligne Claire art style after a trip to France, although my art looks nothing like it. David Mazzucchelli's book Asterios Polyp was a big influence on the way I try to tell a story within a single illustration. I also stopped buying texture brush sets from other designers and created my own.

Artwork by James Olstein

You work in the fields of editorial, brand, packaging, and book illustration - what's your creative process like? How do you take an idea from concept to delivery?

My process is pretty basic. I'm normally commissioned by an Art Director via email. They tell me what they are looking for or we do a call and discuss ideas. I then do a bunch of pencil sketches until we find one that fits. After that I take the sketch right into Adobe Illustrator and finish it up. I only work in vector, so any revisions are normally pretty fast. Once that's approved I send the Art Director a hi-res file and hope they hire me again.

Artwork by James Olstein
Artwork by James OlsteinArtwork by James Olstein

You've worked with a variety of editorial clients including Penguin, Highlights, Sony Music, the LA Times, MIT Technology Review, and Scientific American. When you're designing for a publication, what are some of the unique considerations you have to take into account?

The biggest things to consider are the size of the illustration within the layout and if it's going to be in print, what the colors will look like in real life as opposed to on screen.

How do you approach creative collaboration with your clients?

I love to talk on the phone; I think this is a byproduct of being a freelancer and working by myself most days. Sometimes I think I talk too much on a call, I just get excited to share ideas sometimes. I'll talk your ear off.

Artwork by James Olstein

In your opinion, what makes a truly memorable piece of design work?

I'm partial to something that helps tell a story in a clever way or humorous way. I rarely remember really beautiful detailed illustrations compared to simpler, bold work with a sense of humor.

Artwork by James Olstein

Do you have any favorite tools or resources? Where do you find inspiration?

I like Blackwing pencils for sketching. Sponsor me. I don't use a ton of tools. I work in Adobe Illustrator for almost every project. For inspiration my best ideas come from times where I'm ignoring the internet. I have a lot of ideas while working out. Camping and fishing are big ones for me as far as clearing my head. I get a lot of silly ideas while playing with my son Jimmy who is really imaginative. Things get really ridiculous and detailed.

Artwork by James Olstein

What's one of the biggest career lessons you've learned so far?

Always be pitching your work/cold emailing. No matter what. Find the time each work day to reach out and introduce yourself/share your work. It may feel like you're bothering people, but no one actually knows that you exist.

Artwork by James Olstein

What advice would you give to designers who are just starting out in their careers?

No joke, get a bank account and save your money. If you're like me, you probably have—or had—student loans. If you put yourself through school, the sooner you pay those off the more free you will be. Also graphic design and illustration can be a pricey career. Computers, supplies and app subscriptions are super expensive now. Having a financial safety net makes a huge difference. Especially if you want to do work that you enjoy and it may not be the most high-paying job.

Artwork by James Olstein

What are you working on now and what's up next for you?

I am doing some illustrations of different rodeo sports and working on a children's book about a giraffe named Captain Jasper with author Ryan Buynak. No one knows how he became a captain. Yes, he wears a captain's hat.

To view more of James' work, visit his Portfolio or Dribbble page.

James was nominated by Dribbble. All artwork courtesy of James Olstein.