Tact

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Is their a tactful way to deal with a friend who tends to dress in a manner or has such poor hygiene that makes you feel ill? The only thing I've come up w/ is trying to ignore the issue and not saying anything. Are their situations when you should quietly point out things a friend may be doing that make you uncomfortable or should you keep quiet?

Some tips (in order of decreasing tact):

Keep your distance.

When in a vehicle together, sit next to a window that you can open.

Fan yourself so that the air blows toward your friend.

Keep a scented candle between you and your friend.

Buy your friend cologne or perfume ... a bar of soap ... deodorant ... a jug of industrial-strength pine-oil cleaner ...

Make comments like, "What did you eat, fogawdz sake?" and "Would someone puh-LEEZ light a match?"

Tell your friend, "You stink. Stay away until you bathe and change clothes."

the bigger question is why are they not keeping themselves clean?

I'd say bring it up respectfully if it's really interfering with your ability to have fun together or with your relationships with others. Emphasise that while he is a wonderful friend and you'd like to keep this friendship, his poor hygene makes you feel uncomfortable and want to spend less time with him. In this situation, it's not the person as a whole, but an important aspect of him that can likely easily be fixed, and you should keep this in mind while explaining the situation to him.

I'm actually thinking of three different people; 2 have bad hygiene, one is terrible and another person who I'd say had so-so hygiene and dresses/presents themselves in outfits/styles that are extremely off-putting b/c of their body type (I'm talking about dresses/tight clothes, etc. on a female who should not wear said types of clothing... or trying to look sexy and ended up trashy/gross).

I would tackle the 2 people with bad hygiene first, because other people have probably made the same observations you have and would like to say something, but are simply being too nice to bring it up to them. The person wearing unattractive clothes is less of an issue because they likely don't stink, have bad breath, or make someone instantly uncomfortable. I suggest you bring it up with all 3 of them but focus on the 2 with bad hygiene first.

Hmmm, I think it's nice when people tell me if I smell bad, then again, it would be an awkward thing to say to someone...

"they don't teach tact at the academy"

This is hard. I think being honest is the best way. I don't know any way to be subtle and convey in a indirect way to deal
with your unfortunate problem. All the best.

If you are such a fashionista why not offer to go out for clothes with them. You probably won't have to if you don't know them very well, but it gets them thinking about it. People often try on clothes and their friend gives them critiques easily enough.

Also the classic perfume trick, ease up near the person and spray on some hypo allergenic scent. If they ask, tell them you were using it yourself. Make sure to be just out of sight angle.

Consider the possibility that you are being over-judgmental about it and use a coping technique.

I don't bathe often and have no fashion sense so I know all of the tricks.