IMO, Suikoden I and IV are tied for having the worst and the blandest outfits in the entire series. SII is a step above them, followed by SIII, then SV having the best looking attires.
SI Male - Maas
Mass actually managed to work a beret and a tunic together! That takes some class and some skill, which is why I voted him as best dressed male in SI.
SI Female - Sonya Schulen
Sonya actually looks good in her armor due to its color scheme and the little blue skirt that suspends below her armor.
SII Male - Jess
Jess actually has class amidst an army of barbarians. I love the whole formal look he has what with the tie, dress pants, and dress shoes. However, he seems a little laid back since he wears a vest alone, without the suit.
SII Female - Anita
Just like with Sonya, she can pull off wearing armor and a dress at the same time. Plus, her dress is purple, my fave color!
SIII Male - Nadir
He really looks like an early century nobleman. I love his black and white color scheme, not to mention his silver hair. Even the mask actually goes well with the outfit and doesn't look TOO creepy.
SIII Female - Jeane
She actually dresses with some class in the installment. Actually, she has a lot of class compared to the slutty clothes she has in the other games.
SIV Male - Trishtan
Trishtan wins for best dressed male in SIV due to his combined look of decency and flippancy. Unlike most of the males who are way too unruly or much too formal, Trishtan has, what seems, like a leather vest atop a sleeveless shirt, both with colors that compliment each other. For his bottom, he dons a baggy pair of pants which I much rather prefer to short-shorts (Lazlo, Nalleo) or tights (Snowe Pirate Set, Ugetsu).
SIV Female - Ameria
Well, Ameria was the most classy dressed out of a cast of females with a bad sense of fashion (Jeane's slutty look, Rene's excavator suit, Pecola's drab clothes paired with a ridiculous hairstyle, etc.).
SV Male - Egbert Aethelbald
Egbert may be crazy, but I love his toy soldier uniform look! His green and red suit is absolutely dashing and I love his belt/sash thingy. His pantaloons are not as pronounced as Nadir's (which work for Nadir, but not anyone else) and that hat is just adorable!!
SV Female - Linfa
Chinese dresses are absolutely elegant, and Linfa pulls off the look easily. What contributes to her being the best dressed female is the silk glove she dons on her left arm and her exposed legs. Absolutely gorgeous!!!
SI Male - Juppo
He looks like a damned fool.
SI Female - Meg
SII Male - Gengen
He looks like a boy scout and I don't like that look.
SII Female - Teresa
Teresa is pretty. She really is. And she has a beautiful dress to boot. However, what kills her the most are those damned gloves she wears. Those do NOT go with her dress whatsoever. They make her look extremely foolish, IMO and had she not had those, she would've easily been the best dressed. Now, I understand there were other females who dressed worse than Teresa (Meg, Ayda, Hanna etc.), however, those females don't try in the slightest to look good. Teresa tried, however, and it failed, thus, why I gave her the worst dressed female in SII.
SIII Male - Kenji
NO TANKS. NO SWEATS. NO CHANCE FOR LOOKING GOOD ESPECIALLY WITH A SICKENINGLY LIME GREEN AND PINK COLOR SCHEME.
SIII Female - Iku
The pantaloons. I hate them. Her hips look WAY too big in them.
SIV Male - Brec
Tattered clothes? Fail.
SIV Female - Helga
Tattered clothes that were sown with crappy looking patches? Epic fail.
SV Male - Norden
It wasn't that he was badly dressed, but when in a game where most of the characters have great looking clothes, plain is just as bad as bad.
SV Female - Nelis
Let me just start by saying, I hate the Obel Nation's soldier's uniform. It looked bad in IV and I'm a bit miffed that they brought them back in V. Especially with 3 characters that actually join your party this time. However, Yahr actually looked alright in his. Bernadette was pushing it. Then Nelis came and broke the last straw. How foolish she looks in that silly cone shaped hat with a cape, of all things, attached to it. If it weren't for this one piece of garment, Bernadette would've been the worst dressed of the three, but now, that belongs to Nelis.
Hmm... Didn't make much money. Next time, let's get rich! - Rachel