Συνήθως δεν βάφομαι πολύ όταν πηγαίνω στη δουλειά.

Because βάφομαι is the form Greek normally uses when someone means I put on makeup / I make myself up.

• βάφω = I paint, dye, or color something
• βάφομαι = I put makeup on myself or more literally I make myself up

So in this sentence, δεν βάφομαι πολύ means I don’t wear/put on much makeup, not I don’t paint something much.

Not always. Its exact meaning depends on context.

Common possibilities:

• βάφομαι = I put on makeup
• βάφομαι ξανθιά = I dye my hair blonde
• in some contexts, it can simply mean I color/dye myself

In this sentence, the context makes put on makeup the natural meaning:

• Συνήθως
• δεν ... πολύ
• όταν πηγαίνω στη δουλειά

Together, that strongly suggests everyday makeup, not hair dye or paint.

Greek often leaves out subject pronouns because the verb ending already shows the person.

Here, βάφομαι means I put on makeup and πηγαίνω means I go, so εγώ is not necessary.

You could add εγώ, but then it would sound more emphatic, like:

• Εγώ συνήθως δεν βάφομαι πολύ... = I, for my part, usually don’t wear much makeup...

So the version without εγώ is the normal neutral one.

In Greek, δεν is the normal negation for verbs in statements, and it goes directly before the verb.

So:

• βάφομαι = I put on makeup
• δεν βάφομαι = I don’t put on makeup

That is standard Greek word order. You normally do not move δεν away from the verb.

Here πολύ is being used adverbially, meaning much / a lot.

So:

• δεν βάφομαι πολύ = I don’t put on a lot of makeup / I don’t wear much makeup

Greek very often uses the neuter singular form πολύ as an adverb.

Compare:

• πολύ = much / a lot / very depending on context
• πολλά = many / a lot of for plural countable nouns

For example:

• Δεν διαβάζω πολύ. = I don’t read much.
• Δεν αγοράζω πολλά βιβλία. = I don’t buy many books.

So πολύ is correct here because it is modifying the action, not a plural noun.

Because the sentence describes a habitual action: something that usually happens.

• όταν πηγαίνω στη δουλειά means when/whenever I go to work
• the present tense fits repeated, usual actions

This is similar to English, where you also say:

• When I go to work, ... not
• When I am going to work, ... in this kind of general statement

So the Greek present here is natural because the speaker is talking about a routine.

στη is a contraction of σε + τη(ν).

So:

• σε = to / at / in
• τη δουλειά = the work / the job
• στη δουλειά = to work / at work

This kind of contraction is very common in Greek:

• στο = σε + το
• στη = σε + τη(ν)
• στους = σε + τους
• στις = σε + τις

So πηγαίνω στη δουλειά is literally something like I go to the work/job, but naturally it means I go to work.

Because Greek uses the definite article in many places where English does not.

So Greek naturally says:

• στη δουλειά = literally to the work/job
• but in real English this is just to work

This is normal and idiomatic. You should not try to match article usage word-for-word between Greek and English.

Other similar examples:

• πάω στο σπίτι = I’m going home
• είμαι στο σχολείο = I’m at school
• πάω στην τράπεζα = I’m going to the bank

Συνήθως means usually, and here it sets the general time/frequency for the whole sentence.

Putting it first is very natural:

• Συνήθως δεν βάφομαι πολύ όταν πηγαίνω στη δουλειά.

But Greek word order is fairly flexible, so you can move it:

• Δεν βάφομαι συνήθως πολύ όταν πηγαίνω στη δουλειά.
• Όταν πηγαίνω στη δουλειά, συνήθως δεν βάφομαι πολύ.

These versions are possible, but the original sentence sounds smooth and neutral.

In this sentence, it can feel like either, depending on how literally you want to translate it.

Because the sentence describes a habit, όταν has the sense of:

• when
• or more specifically whenever

So:

• όταν πηγαίνω στη δουλειά = when I go to work
• but the idea is really whenever I go to work, this is usually what I do

That habitual nuance comes from the whole sentence, not just from όταν alone.