1

In the dictionary

dress [intransitive, transitive]: to put clothes on yourself/somebody

dress (in something) I dressed quickly.

dress somebody (in something) She dressed the children in their best clothes.

Get up and get dressed!

The children spend hours dressing and undressing their dolls.

and

put something <-> on

​ to dress yourself in something

Hurry up! Put your coat on!

Is it correct to say "dress the teddy bear in the glasses" or "put the glasses on the teddy bear"?

But I couldn't find sentences "dress somebody (her/him...) in the glasses" on the internet but I found a lot of sentences "put the glasses on somebody (him/her...)"

But the dictionary only says "put something on" or "put on something" (eg, put my clothes on / put on my clothes) but not "put something on somebody" (eg, put the clothes on him)

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"Is it correct to say "dress the teddy bear in the glasses" or "put the glasses on the teddy bear"?"

I am assuming you are asking if the first option is idiomatic, because grammatically it is fine. I have personally never heard anyone say that: "...dress [somebody/something] in the glasses". I think your finding

"But I couldn't find sentences "dress somebody (her/him...) in the glasses" on the internet"

supports that.

As you have found, "dress" is usually used when referring to clothing (not talking about salad dressing here). From Cambridge, "dress" (v) means

  • to put clothes on yourself or someone else, especially a child.
  • to wear a particular type of clothes
  • to put on formal clothes for a meal

As such, I would not use the word to refer to putting on glasses. When we talk about accessories that we use, for example shoes, a tie, cufflinks, a hat, a belt, a watch, sunglasses, and ornaments, we use the phrasal verb "put on [something]". You can also use "put on [something]" when referring to clothing.

The idea is to put the hat on when [children] are distracted by something else. - How To Get Your Baby To Wear A Hat.
Kim had forgotten to put his watch on. - Macmillan

We say

I helped them put on their shoes/tuxedo/tie.

But when it comes to an inanimate object, we can simply say

I put the hat on the teddy bear.

If you are doing something more - like putting clothes, shoes, a hat, and glasses on the bear - then you can just say

I dressed the bear.

2

Glasses are not considered clothing. It is therefore not appropriate to say that you are dressed in glasses. Therefore, you put the glasses on and take them off. The same applies to the teddy bear.

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