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I've learnt that we should use the present perfect or the past perfect with "since," as in:

I haven't been to England since I was a child.

And in the past:

I had worked there since I (had) left school.

My question is: in spite of this rule, are there cases where we can use simply the past simple? I am wondering about a sentence like this:

She had looked liked a boy since she (had) cut her hair.

For the second part, my grammar books explain that the simple past is possible (cut/had cut) but for the first part (had looked like a boy), I am under the impression that "she looked like a boy since she (had)cut her" is possible?

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I think quite a few native speakers would have no problem with:

She felt she had looked liked a boy since she cut her hair.

You need a reason for the past perfect, hence "she felt" here -- just to create a context. It could be almost anything that places her looking like a boy in the past relative to a more recent past.

But many speakers would avoid "since she cut" and avoid a tensed verb altogether. We tend to avoid such tense-constipation, past-perfect-upon-past-perfect

She felt she had looked like a boy after she had cut her hair.

and for that the participle is handy

She felt she had looked like a boy after cutting her hair.

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In this case, you'd probably have to use the past perfect. The way she looked is relative to another past action, her cutting her hair, so we'd have to use the past perfect to show this link.

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