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How to Dress for Success in New Greeceland, part 1 featured teenage Hercules, Iolaus and Jason - now here's the adult version. So to speak.
Let's start with Amazon Women, the first of the TV movies:

Okay, this is perhaps not the best shot for showing what they are wearing, but I am helpless in the face of intense manly affection.
The loose, open blue shirt Iolaus is wearing looks like linen to me, and the color goes beautifully with his eyes (he looks really really edible in this entire opening scene) and we will never see him wear it again. Hmf.
Hercules' yellow sleeveless undershirt looks a lot like what he was wearing for most of the series, the suede overshirt less so. He was also having an appalling hair day, which maybe explains why he was being so uncharacteristically bitchy all through this episode.
On their way to see the Amazons, they come in for some rough weather, and amazingly they are DRESSED FOR IT.

I don't think we ever see them wear this kind of weather-appropriate clothing in snow again, not even after Prometheus is imprisoned and the world freezes over. Of course, they don't usually carry anything like a change of clothing with them either, and I surmise that they were only so well equipped this time because they started out from Thebes, and Alcmene loaded them down with blankets and cloaks and a lot of helpful advice about not letting their feet get wet.
Then their day gets even worse, especially for Iolaus who is Mostly Dead, while Hercules ends up like this:

Which is really a good look for him. He took his shirt off plenty of times after this, but as far as I can remember this was the only time where he was gagged as well (not to mention trussed up on a cart and paraded around town as beefcake-on-a-stick).
And this was also something we didn't see again. Well, unless you count the blanket falling off hips bit in the blooper reel. I do love that this is how we see Hercules mourning for Iolaus. It's very much like he's holding on to a person who isn't there.

On to Maze of the Minotaur, where the clothes have changed a bit:

Hercules' yellow vest is a bit rougher than the one he wears later - this one does rather look like it was ripped open by teeth - but still basically the same as what we see him wear through most of the series, and so are the pants.
Iolaus' blue patchy vest is new, and looks similar to the purple one he wears most of the time. I'm glad they switched to purple, it does 'pop' more onscreen.
The vests would come off soon enough, anyway -

I am of course just posting this pic to draw your attention to Iolaus' belts. *cough* The one at the top is the hooked belt that actually holds his pants up, the other is slung lower around his hips and usually holds his sheathed sword. Sometimes he carries it over his shoulders instead.
Also please note that he is wearing pants in this picture, though probably matters were about to progress to a point where pants became optional.
Now look at this travel snapshot, where Hercules and Iolaus are off to deal with the minotaur:

I actually had to take a new screencap here, since I skipped it before, but there's a whole travel sequence in which Iolaus is wearing a hoodie, tall boots and apparently NOTHING ELSE. Hence the title of this post.
At the campfire that night, Iolaus has put his pants back on:

and they're both wearing blankets, so probably he put them on again because delicate parts of him were getting cold. Or something. You tell me!
To be continued. :-)
Let's start with Amazon Women, the first of the TV movies:

Okay, this is perhaps not the best shot for showing what they are wearing, but I am helpless in the face of intense manly affection.
The loose, open blue shirt Iolaus is wearing looks like linen to me, and the color goes beautifully with his eyes (he looks really really edible in this entire opening scene) and we will never see him wear it again. Hmf.
Hercules' yellow sleeveless undershirt looks a lot like what he was wearing for most of the series, the suede overshirt less so. He was also having an appalling hair day, which maybe explains why he was being so uncharacteristically bitchy all through this episode.
On their way to see the Amazons, they come in for some rough weather, and amazingly they are DRESSED FOR IT.

I don't think we ever see them wear this kind of weather-appropriate clothing in snow again, not even after Prometheus is imprisoned and the world freezes over. Of course, they don't usually carry anything like a change of clothing with them either, and I surmise that they were only so well equipped this time because they started out from Thebes, and Alcmene loaded them down with blankets and cloaks and a lot of helpful advice about not letting their feet get wet.
Then their day gets even worse, especially for Iolaus who is Mostly Dead, while Hercules ends up like this:

Which is really a good look for him. He took his shirt off plenty of times after this, but as far as I can remember this was the only time where he was gagged as well (not to mention trussed up on a cart and paraded around town as beefcake-on-a-stick).
And this was also something we didn't see again. Well, unless you count the blanket falling off hips bit in the blooper reel. I do love that this is how we see Hercules mourning for Iolaus. It's very much like he's holding on to a person who isn't there.

On to Maze of the Minotaur, where the clothes have changed a bit:

Hercules' yellow vest is a bit rougher than the one he wears later - this one does rather look like it was ripped open by teeth - but still basically the same as what we see him wear through most of the series, and so are the pants.
Iolaus' blue patchy vest is new, and looks similar to the purple one he wears most of the time. I'm glad they switched to purple, it does 'pop' more onscreen.
The vests would come off soon enough, anyway -

I am of course just posting this pic to draw your attention to Iolaus' belts. *cough* The one at the top is the hooked belt that actually holds his pants up, the other is slung lower around his hips and usually holds his sheathed sword. Sometimes he carries it over his shoulders instead.
Also please note that he is wearing pants in this picture, though probably matters were about to progress to a point where pants became optional.
Now look at this travel snapshot, where Hercules and Iolaus are off to deal with the minotaur:

I actually had to take a new screencap here, since I skipped it before, but there's a whole travel sequence in which Iolaus is wearing a hoodie, tall boots and apparently NOTHING ELSE. Hence the title of this post.
At the campfire that night, Iolaus has put his pants back on:

and they're both wearing blankets, so probably he put them on again because delicate parts of him were getting cold. Or something. You tell me!
To be continued. :-)