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“I am fearful of that being the tweaks and adjustments most clients ask for are easier to play-around with in the design of the static jpeg representation of the site”

At first, especially considering designers who are a bit uncomfortable working with CSS (I work with a few), this seems like a logical option.

But, have you ever been in the experience of working on a large brand site, where there’s well in excess of 15 basic templates (for a CMS like Joomla or Drupal), and multiple pages having variations of functionality and layout?

A “simple tweak” in a JPG becomes a WEEK LONG onslaught of digging through 15+ PSD files making the changes to all the “Rounded corner” buttons, and changing that “baby-poop” green. Then delivering the site in a stack of JPGs (that auto shrink) in their email client, causing them to call back and complain about font size, and having concerns about where the fold is…

Or, while the client is on the phone saying “Hang on just a min…”

Put them on hold, change a few selectors in the CSS. Save -> Upload and say “Okay, refresh and look now”

I think it really has to do with education.

1. Us educating our clients.
2. Designers learning to design in the medium.

I don’t think that necessarily means NOT using photoshop, but I think it means, not showing the client JPGs. I would use photoshop strictly for assets, backgrounds and major design elements, and drop them in.

I don’t think using CSS leads to boxy designs, I think uncreative designers who are used to the Photoshop only method can’t bridge the gap from Photoshop -> CSS. It just takes time and practice to adapt to that workflow. And you’ll make some kick-ass work much faster that way.