Learn Hardcore Chinese: wǒ zhè gè màozi dài le hěn duō nián le, juéde bǐ xīn màozi gèng shūfu. - I’ve worn this hat for many years; I feel it’s more comfortable than a new one.

我的帽子 = my hat (neutral possession)
我这个帽子 = this hat of mine (highlighting this one, often with a sense of familiarity or specialness)
You can also say 我的这个帽子, which is closer in meaning to “this particular hat of mine” and sounds a bit more explicit.

Similar patterns:

我这个朋友 – this friend of mine (often with some attitude, good or bad)
他那个同事 – that colleague of his

So 我这个帽子戴了很多年了 suggests “this particular hat that I own, I’ve worn it for many years,” slightly more emotive than a plain 我的帽子.

In the breakdown I see 这个帽子 as three parts. Is 这 a separate word from 个, or should I think of 这个 as one word?

Functionally, you should think of 这个 (zhège) as one phrase meaning “this” (as in this hat).

What’s going on:

这 = “this” (demonstrative)
个 = a general measure word (classifier)
Together 这个 = “this (one)” and usually written as one chunk before a noun: 这个帽子 (“this hat”).

The character-by-character spacing (这个帽子) is just for teaching/reading convenience. In normal text you’ll see 这个帽子, not with spaces between 这 and 个.

Why is 个 used as the measure word for 帽子? Isn’t 顶 the classifier for hats?

You’re right that the more specific classifier for hats is 顶.

Precise: 一顶帽子, 这顶帽子 – one hat, this hat
General: 一个帽子, 这个帽子 – also possible in everyday speech

Details:

顶 is the “proper” classifier for hats, caps, etc.
个 is the all‑purpose classifier used in casual speech when people don’t bother with the specific one. It doesn’t sound wrong, just less precise.

You can say:

我这顶帽子戴了很多年了 – sounds a bit more natural/idiomatic than 我这个帽子戴了很多年了, especially in careful speech.

What exactly does 戴 mean here, and how is it different from 穿?

戴 (dài) means to wear for items that you put on your head, face, hands, or as accessories.

Typical uses of 戴:

戴帽子 – wear a hat
戴眼镜 – wear glasses
戴手套 – wear gloves
戴项链 – wear a necklace
戴口罩 – wear a mask

穿 (chuān) is for clothes you put your body into:

穿衣服, 穿裤子, 穿鞋 – wear clothes, pants, shoes

So:

戴帽子 is correct.
穿帽子 is wrong.

Why are there two 了 in 戴了很多年了? What does each 了 do?

The two 了 have different roles:

The first 了 after 戴 (戴了) is aspect 了 (perfective):
- It marks that the action has been carried out / completed in some sense.
- 戴了很多年 = “wore (it) for many years / have worn (it) for many years”.
The second 了 at the end of the clause (…很多年了) is sentence‑final 了:
- It marks a current state resulting from past action or a change of situation.
- Here it implies “it has already been many years (up to now)”.

Together, 戴了很多年了 usually means:

“have been wearing it for many years (and this is still true now).”

Can we delete one of the 了 in 戴了很多年了? How would that change the meaning?

Roughly:

Keep both (standard continuous‑up‑to‑now meaning):
- 我这个帽子戴了很多年了。
  → I’ve been wearing this hat for many years (and I still have it / it’s still relevant now).
Delete the second 了 (only verb‑了):
- 我这个帽子戴了很多年。
  → Grammatically possible, but often feels a bit incomplete in conversation. It sounds more like narrating a finished stretch of time in the past:
  “I wore this hat for many years (unspecified whether it’s still true now).”
- Context would have to make the time frame clear.
Delete the first 了 and keep only the sentence‑final 了:
- 我这个帽子戴很多年了。
  → In standard Mandarin this is not natural; you normally need the 了 after the verb in this pattern. Most textbooks treat this as incorrect or at least very non‑standard.

The usual pattern for “have been doing X for Y time (up to now)” is:

(Subject +) Verb + 了 + Duration + 了
e.g. 我学中文学了三年了。, 他在这儿住了五年了。

What does 很多年 mean exactly, and how is it different from 多年 or 好几年 / 好多年?

All relate to “many years,” but with slightly different flavor.

很多年
- Very common in speech.
- Plain “many years,” neutral.
- 戴了很多年 = have worn it for many years.
多年
- A bit more formal/literary than 很多年.
- Very common in written Chinese or slightly elevated speech.
- Often appears as 多年来, 数十年 / 数年 / 十多年来 etc.
- You could say 我戴这顶帽子已有多年, which sounds more formal.
好几年 / 好多年
- Colloquial, with a sense of “quite a few years / at least several years”.
- Slightly more emotional or emphatic.
- 戴了好几年 / 好多年 feels like “a good few years,” “more than just a couple of years.”

In the given sentence, 很多年 is the most neutral and natural choice.

Could we put 很多年 somewhere else in the clause, like before 戴?

Not in a natural way. Duration expressions like 很多年 normally go after the verb (and often after verb‑了) in this pattern:

戴了很多年 – correct and natural
很多年戴了 – odd / not the same meaning
戴很多年了 – needs verb‑了 after 戴: 戴了很多年了 is preferred.

More generally, common patterns for “do something for X time” are:

Verb + 了 + Duration + 了
- 我在这儿住了三年了。
Or with object fronted:
- 我戴这顶帽子戴了很多年了。

But putting 很多年 before the verb (很多年戴) either sounds wrong or changes to something like “for many years (I) wear…”, which is not how Mandarin usually structures it.

Why is there a comma before 觉得? Shouldn’t there be a subject like 我觉得 or 我觉得它…?

The comma separates two clauses, but the subject is understood from context and doesn’t have to be repeated.

The full, fully explicit version could be:

我这个帽子戴了很多年了，我觉得它比新帽子更舒服。
(I have worn this hat for many years; I feel it is more comfortable than a new hat.)

In conversational Chinese it’s very common to:

Introduce a topic: 我这个帽子戴了很多年了 (about this hat of mine…)
Then comment on it, with the subject omitted because it’s obviously the same 我:
觉得比新帽子更舒服。

So the underlying structure is basically:

（我）觉得（它）比新帽子更舒服。

Both 我 and 它 / 这个帽子 are recoverable from the previous clause and can be omitted.

How does the comparison with 比 and 更 work in 觉得比新帽子更舒服?

The basic comparative pattern is:

A 比 B (更) Adj
→ A is (even) more Adj than B.

Here the “A” is understood (the hat we’re talking about), and the structure inside the second clause is essentially:

（这个帽子）比新帽子更舒服。
= This hat is even more comfortable than a new hat.

Breaking it down:

比 marks the item you compare against – think “compared with / than”.
新帽子 is the standard of comparison: “new hats”.
更 = “even more / still more”, intensifying the comparison.
舒服 is the adjective “comfortable”.

With 觉得, it’s:

（我）觉得（这个帽子）比新帽子更舒服。
= I feel (this hat) is more comfortable than a new hat.

Can we drop 更 in 比新帽子更舒服? What difference would that make?

Yes, you can say 比新帽子舒服:

比新帽子舒服
→ more comfortable than a new hat
比新帽子更舒服
→ even / much more comfortable than a new hat (slightly stronger, more emphatic).

So:

比 + N + Adj is already a valid comparison (“more Adj than N”).
更 just boosts the degree: even more, still more, much more.

In practice, speakers often include 更 with polysyllabic adjectives or when they want to stress the difference, but it’s not grammatically required.

Why is there no 的 between 新 and 帽子? Can we say 新的帽子 instead of 新帽子?

Both 新帽子 and 新的帽子 are grammatically correct; the difference is subtle.

新帽子 (Adj directly before Noun):
- Very common and natural when the adjective is a single syllable (like 新, 大, 小, 好, 坏, etc.).
- Felt as a tighter adjective–noun unit: “new hat”.
新的帽子 (Adj + 的 + Noun):
- Also correct.
- Can sound slightly more emphatic or descriptive, or may appear when the adjective phrase is longer or more complex.

Some parallels:

红苹果 / 红的苹果 – red apple(s)
旧房子 / 旧的房子 – old house

In your sentence, 新帽子 is the most natural, default choice. 新的帽子 would not be wrong; it just lightly changes the feel, often with a bit more focus on the “newness.”

Why doesn’t 舒服 have 很 in front of it, like 很舒服?

Normally, when an adjective is used as a predicate in Chinese, you often need a degree adverb like 很:

这顶帽子很舒服。 – This hat is comfortable.

Without 很, a bare adjective often sounds either comparative or unnatural. But in your sentence, 舒服 is already modified by 更:

更舒服 – even more comfortable

Since 更 itself is a degree adverb, you don’t add 很 at the same time. You wouldn’t say 更很舒服. So:

帽子很舒服。 – neutral statement (is comfortable)
帽子更舒服。 – is more comfortable (than something)

Would 我戴这个帽子戴了很多年了 be acceptable, and how is it different from 我这个帽子戴了很多年了?

Yes, 我戴这个帽子戴了很多年了 is acceptable and actually quite natural. It has a slightly different structure and focus:

我这个帽子戴了很多年了。
- Treats 我这个帽子 as the topic.
- Literally: “As for this hat of mine, (it) has been worn for many years.”
- Focus is more on the hat itself as an object that has this history.
我戴这个帽子戴了很多年了。
- Explicit subject–verb–object: “I wear this hat.”
- Then repeats the verb with duration: 戴了很多年了.
- Emphasis is a bit more on my action of wearing it for many years.

Both are fine in spoken Mandarin. The given sentence is slightly more topic‑comment style; the alternative is more explicitly “I have been wearing this hat for many years.”

Why isn’t there any 是 in the sentence, even though in English we’d say “it is more comfortable”?

Chinese doesn’t use 是 in front of adjectives the same way English uses “to be.”

English: It is comfortable.
Chinese: 它很舒服。 (no 是)

Key points:

In Chinese, many adjectives behave like stative verbs; they can directly function as predicates:
帽子很舒服。 – “(The) hat is comfortable.”
是 is typically used to link two nouns / noun phrases:
他是老师。 – He is a teacher.
But not before plain adjectives in neutral statements.

In your sentence:

比新帽子更舒服 already has 舒服 as the core predicate; you do not say 是更舒服.
So 觉得比新帽子更舒服 = “(I) feel (it) is more comfortable than new hats,” with no 是 needed.

How would I say “I used to wear this hat for many years, but I don’t wear it anymore”?

You need to separate the past period from the current situation clearly. For example:

以前我戴这个帽子戴了很多年，但是现在不戴了。
→ Before, I wore this hat for many years, but now I don’t wear it.

Or:

我这个帽子以前戴了很多年，后来就不戴了。
→ I used to wear this hat for many years; later I stopped wearing it.

Here, the duration 戴了很多年 is still expressed with 了, but the added time words (以前, 后来, 现在不戴了) make it clear that this is a past habit that has ended.