His influences include British "Golden Age" book illustrator Arthur Rackham, Czech Art Nouveau painter Alphonse Mucha, and comic-strip artist Hal Foster, among others.

One notable publication from this early period was The Horns of Elfland (ISBN 0-915822-25-3) published by Archival Press in 1979, which Vess wrote and illustrated.

[9] In 1991 he illustrated the official comic-book adaptation of Steven Spielberg’s Hook and had an eleven issue run (#129–139) as cover artist of Swamp Thing by DC Comics in 1993.

He illustrated "The Land of Summer's Twilight", one of the four episodes in the original The Books of Magic mini-series,[10] and worked on three issues of Gaiman's critically acclaimed The Sandman series.

In 1999, Vess's own Green Man Press produced a portfolio as a benefit for his wife Karen, injured in a car accident, titled A Fall of Stardust, which contained two chapbooks and a series of art plates.

(ISBN 0-06-083808-6) Beginning in 1995 Vess self-published a biannual series of comics entitled The Book of Ballads and Sagas through his Green Man Press.

[5] In this series Vess illustrated adaptations of traditional Scottish and English ballads written by a variety of contributors, including Emma Bull, Charles de Lint, Neil Gaiman, Sharyn McCrumb, Jeff Smith, and Jane Yolen.

Vess worked with longtime friend and writer Charles de Lint on at least half a dozen publications, including Seven Wild Sisters (Subterranean Press, 2002) and related projects A Circle of Cats (Viking, 2003), and Medicine Road (Subterranean Press, 2005, as well as a later edition by Tachyon Publications, 2009), along with others mentioned above.

In 2021 Vess illustrated Joanne Harris's Honeycomb; a collection of 100 interconnected fairy stories forming a mosaic novel.

[21] Harris describes the process of working with Vess as follows:[22]Through the lens of Charles’ art, the Silken Folk of my stories are neither entirely human, nor overly insectile: and their beauty is slightly monstrous, yet altogether bewitching.

I can think of no finer magic than this.In a 2004 interview, Vess cited among many artistic influences, beginning with the 19th-century British book illustrator Arthur Rackham, saying, I discovered his work while I was still in college and immediately fell completely in love with it.

Among the living I count Michael Kaluta, Alan Lee, Brian Froud, Lizebeth Zwerger and Terri Windling.