grammar - Is it wrong to use "would wear glasses" in the meaning of a habit in the past

Finally I did find an example of usage like that:

He would always wear exactly the same brown pullover and grey trousers.

And in terms of "repeated actions" it does make sense, because when you wear glasses or something else you put it on and take it off repeatedly, so you are not actually in permanent state of wearing it.

Going back to my original example, as far as I understand

I would always wear glasses when I was a teenager.

is grammatically correct, isn't it?

Thanks to @rogermue answer I realized that probably both options are correct, but I would notice that "when I was a teenager" gives quite a clear notion that the sentence talks about past habit, so I don't think "would" is so ambiguous in this case. Though, I'm still not sure if the sentence is ok without "always":

I would wear glasses when I was a teenager.

Is it?

I'm quite sure, that both following sentences are correct, but they have some difference in attitude:

I used to wear glasses when I was a teenager. (Just the fact)

I would always wear glasses when I was a teenager. (It is a lot more emotional and emphasize the typical, repeated action)

Am I right?

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