I usually begin by writing a tight brief so the artist knows exactly what I want for a 'The Outsiders' piece. Include who (which characters or scenes), what (style: realistic, stylized, chibi, comic panel), where it will be used (social, print, sticker), size, colors, and any reference images. That short paragraph saves so much back-and-forth and shows the artist you respect their time.
Next I scout artists on places like Twitter/X, Instagram, ArtStation, DeviantArt, Etsy, and commission threads on Reddit. When I find someone whose style fits, I send a polite message with the brief, my proposed budget, and a question about availability. I always ask about payment method (PayPal, Ko-fi, Gumroad), deposit percentage, revision policy, and estimated turnaround. Contracts or even a simple written agreement in DMs make things cleaner.
Finally, I think about rights and delivery: ask for file types (PNG/TIFF for print), resolution, and clarify if you want commercial use. If you plan prints, budget extra for print-ready files and maybe color adjustments. Tip generously if they went above and beyond, and credit them when you post. Getting a piece of 'The Outsiders' done this way feels collaborative and honestly pretty rewarding—makes the characters feel even more alive to me.