By the way, your web designer is no good.

What matters is that the client is happy with the work. Now, if this designer is doing something that is actively detrimental to the org that nobody there has the technical expertise to understand, that might be the one time it's appropriate to butt in. In that case, it might be appropriate to arrange a lunch with someone you know well from your time there and plant the seed in a low-stakes way. I'd still stay out of it unless it's a really big freakin' deal like what the designer is doing is going to cause the org to lose thousands of people's personal information and lead to a PR disaster, large legal bills, and liability to third parties. What it sounds like is actually happening is that the new design is perfectly functional and aesthetically pleasing, but not in keeping with what the kids are doing. In that case, it's not your place to tell someone they shouldn't be happy with it because it's a matter of opinion.

I still feel like it is not my place, but what do I have to lose anymore? Your credibility. What you are proposing really isn't done in the business world, and it would not be well received.

Not your problem. They'll ask you if they want your opinion. That's as far as you need to go for your answer. Further, if they ask you, feel free to request a consulting rate to provide an opinion.

What you are proposing here is informing people that what they [already] see [with their own eyes] is terrible. I am sure you have good intentions but it won't necessarily be perceived that way (1). (1) What I am referring to here is the tendency of people in our industry (software engineering and graphic design) to "audit" other people's work. Whenever you have the urge to audit - unless of course it is specifically your job - try to understand that the people on the receiving end usually don't see you as a guru raining down valuable advice but rather as a person with a superior attitude and lack of experience. You probably envision your former boss being grateful but busy people with responsibilities (i.e. people who have an impact your career) tend to get annoyed when they have to deal with the "auditor" in a professional manner, i.e. address their concerns, maintain an email trail of decisions being made, make sure the parties involved don't get offended, and so on.

If this is a normally talented designer as you say, there is a good chance the sites look like that because they have been instructed to design them like that. I say this as someone who has designed websites for technophobes, which is its own circle in hell.

Another expanded way to look at it, as someone who's slightly fallen in to this type of "oh, one more thing" trap. Assuming the BEST POSSIBLE outcome where they go "Well golly gee fuck, we need to fix that crap asap then!"... You are now married to this project. In the absolute la la land fantasy version of this, you are going to be thrust in to this shit and made to deal with it and the entire hit yourself in the face with a hammer process of "Well i agree with you, but tell XYZ other people why they should do this". It'll be like that Kevin Smith http://www.youtube.com/watch?v=vgYhLIThTvk where you're now the salesman, being shuffled around from person to person to convince everyone who needs to push the so you think you can dance style buzzer button. And after that? now 99% chance you have to work with designer guy who you respected who probably now resents the shit out of you. If not, now you have whatever deadline he had to star from scratch and do everything. I can't imagine a way this plays out without them(correctly, honestly!) thinking you're trying to jam your weiner in the works here. The best possible outcome for you is that they contract to you to do this shit. Under really terrible circumstances. And this is of course ignoring the fact all of that is incredibly unlikely. This is a "Best case scenario i get punched in the face" type of situation here. Any action you take here will have a negative result for you even if you're in the twilight zone universe and it results in a "job" for you. Never bring this up again. People a couple of stations down the train track from you who have done shit like this REALLY wish they could go back and unsay "Hey, you know this is what i think about this. Shouldn't it be done XYZ way instead?" because you either get whack-a-moled in some way or now it's CONGRATULATIONS GOOD JOB SOLDIER NOW GO FIX IT. "a problem without a solution is just another problem" really applies here, among a million other things.

degustibus non disputandem est. Looks ain't everything. But they may in fact like the way it looks. OTOH if there is a problem with the code, and something is not working I would mention it to a friendly former co-worker.

What do you think they will do with the information, especially since their new sites just went up? "Hi, I know you paid this person money to design the site, but it looks terrible." Then what? Do you think they will hire someone else to redo all that work? Almost definitely not, and now you just look unprofessional. There's no upside to saying anything.

Stay out of it. For all you know, the designer was constrained by input from the other stakeholders. Possibly even the one you're thinking of complaining too.