Wesley's season one uniform?

In my opinion the easiest and most likely in-universe answer is that in the time frame between Seasons 1 and 2 Starfleet changed the design for actin ensign uniforms from the sweatshirt with the three division stripes to the grey number.
Just like they phased out the Skants during roughly the same period and updated the standard uniform shortly after (between seasons 2 and 3)
Of course that all just once again shows how ridiculously often Starfleet seems to change their uniforms.

 

As another person said, IDK why he didn't just wear a regular uniform with no insignia while on duty.

His jumpsuits always looked like costumes from bad Star Wars knockoffs.

 

I honestly get the sense that all the costuming choices on TNG boil down to inherently disliking the homogeneity of the TOS standard.

Both Wesley &Troi were put in other attire. Worf was given accoutrement. The doctors were given variants, & even Picard himself would begin applying his own variants. About the only time they moved toward uniformity is when Troi put on the science colors, in S6 (that no one else on the bridge was wearing at the time, mind you. So also not quite homogenous)

Putting Wes in standard uniform gives him less distinctiveness... which was apparently an important aspect to them. I actually don't mind that he graduated to it, as that kind of development was an integral part of his character. Apart from the above ridiculed butt flaps, I'd think a gray variant for acting officers is suitable

 

TOS had variants, too. Kirk had two different wrap arounds. McCoy had a doctor's smock. Troi's costumes were about making her "sexy". Not unlike the minis for women in TOS.

 

Great. Now I won't be able to unsee that.

I always thought the season 2 uniform was fine, and was presumably some kind of official uniform for aspiring Starfleet Academy entrants. Basically a kind of Starfleet Boy Scouts/Air Cadets thing.

 

I always figured it was a costume snafu. The "flaps" were supposed to close but never did, so they just said "screw it, no one will notice!"

 

Chapel's nurse go-go dress "uniform" also looked different from the regular go-go dresses "uniforms" Uhura and the other female crew members wore.

 

Can't disagree about Troi, but the TOS variants seemed subtler. The TNG uniform seemed like it bore more similarity to the TOS film style, which were some of the most homogenous

 

Scotty and Kirk both had variants in the movies as well.
And McCoy had the gown in TWoK

 

Dr. Crusher literally just wore a lab coat over her uniform, which otherwise was a standard uniform,and she didn't even wear it all the time.
Diana Mulder was middle aged when she played Pulaski and requested a variant that would be less revealing than the tight body suits the actors wore at the time.
Troi was not planned to be out-of-uniform in the beginning, but the producers felt that she looked (Hollywood) pudgy in the bodysuit so they tried to put her in a scant and finally put her in civilian garb that would show off her breasts to get horny teens to tune in (it was a time before the internet) And even so they pressured her into losing weight.
Worf's baldric is worn over the standard uniform to highlight his Klingon heritage.
And Wesley was an acting ensign, something that (as far as I know) never showed up on TOS, due to there being no children/teens on board.

 

We were robbed of Grey Onesie Picard

 

TMP mixed things up way more than the tv show did imho