Star Trek

Because they wanted to show that it was "the Future", and in "the Future" (at least to some people's minds) people have to dress weirdly.

They seemed to get over that on occasion. I think the later white dress uniforms were very stylish.

And I imagine those triangular flaps in the collars of civvies to be rather like the 24th century equivalent of bell-bottom trousers: People will look back at them in ten years' time and wonder, "Did we really wear those?"

The TOS crew in civilian outfits was OK  (I absolutely love that Spock's blue/brown outfit in Errand of mercy), the only big FAIL was Spock's disguise in Assignment:Earth  (Yes, that one with Virginity protection hat- no woman looks at you twice).

And yes, the TNG era civilian outfits are maximally ridiculous and/or hideous.  And I thought only Romulan soldiers and politicians wear The Shoulderpads-until I realised in Unification, that ALL THE ROMULANS wear them!

 There were some bright exceptions (some Ambassador (?) in long plain red dress, dunno her name nor the episode where she appeared)

And I like the outfits in AbramsTrek. Especially Spock Prime's winter coat with hood and the asymetric suit. And Amanda's dress and Vulcan school uniforms were cool.

Quick! Cover your eyes!

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And Sulu had that blue shirt and the cloak thing in the Search for Spock, and Chekov had this in the search for Spock:

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Reminds me of a Mr. Rodgers sweater:

(.........)But I'll give you this lame outfit from TOS for free:

Yes, that outfit is lame, but it is Kirk's common bad posture, what caught my eye.  Maybe he should have been aware, what high heels and (possibly) lifts in his boots will do with his spine.

^ Kirk's checking out the outfits too, if you notice!

I liked Jake's clothes.  His later ones were pretty cool looking.  And when I was younger I wanted that purple thing that he wore.  

But particularly bad were the outfits in TVH. Especially Spock's robe. It seemed to me he was pulled out of bed and went right on the mission without changing the clothes (I haven't seen the beginning). Even the boots looked like socks with soles. I understand the robe must be a comfortable piece of clothing- you can hang out all the day long without getting sunburn and being overheated, but it looked like a Vulcan equivalent of sweatpants. Reminded me of Arthur Dent on his way through space, wearing bathrobe all the time. But Spock is not Arthur Dent.

I believe that aside from having smart tech. combined into it, the attire of the future will be loose fitting for the most part; probably fashioned after Asian and Mid-Eastern fashion. Tight fitting clothing will probably be used for mostly intimate purposes, however, I could be wrong; I'm not a prophet or futurist.

Costume design in Star Trek has always been bloody awful.

Star Trek never really looked at clothing technology.  How it might wear better, how it might help keep you cool when it's hot or warm when it's cold.  Mostly, it was uniforms on a climate regulated Star Ship.  There wasn't even warmer clothing for species from warmer planets and cooler clothing for species which liked it cooler.  This was not a well considered part of the series.

If you can beam down everywhere on the planet surface while exploring new worlds, why to go to area with -20 or +35  °C, when you can have some nice 20°C, as on the ship?

Yes, and they started quite good with The Cage grey field jackets.The crew looked like a bunch of mice while wearing them, but I found it somewhat stylish, with the tight pants and heels. Quite dated and not the best fitting, but also not bad. And they could hide all the phasers under it.

Then in TMP, godawful vomit-colored field jackets.(Well, at least nobody would notice, if you have an alcohol accident). And then TWOK-era with slightly better, but still bad looking winter uniforms...

In the case of other species, we have only Spock in TOS and Worf in TNG. As we could see, Spock is quite benevolent to temperetures- after he spent some uncomfortable time in -40°C, he unfreezed the ears and, unlike Bones, was OK. I suppose that his problem in Deadly years was a side effect of radiation illness and he would feel cold even if he sat right into the fire then.

And Worf seemed to have no problem, except the episode where the crew de-evolved. 

The "Sensory web' the blind woman wore in an episode of TOS was beautiful.

The uniforms are way dorkyer in person. Especially TOS ones. I do like the Enterprise ones, though. They seem practical. Especially the bright blue underwear.