Στην καινούρια δουλειά δεν ξέρω αν πρέπει να φοράω στολή ή απλά ρούχα.

Στην is a contraction of σε + την.

• σε = in / at / to
• την = the (feminine accusative singular)

So Στην καινούρια δουλειά means in/at the new job.

This contraction is very common in Modern Greek:

• σε + τον = στον
• σε + τη(ν) = στη / στην
• σε + το = στο

The final -ν in στην is often kept before vowels and certain consonants, and here it appears before καινούρια.

Yes. καινούρια means new.

In this sentence:

• καινούρια = new
• δουλειά = job / work

So η καινούρια δουλειά = the new job.

A learner should also know that Greek has more than one common word for new:

• καινούριος / καινούρια / καινούριο = new, brand-new, new in a practical/everyday sense
• νέος / νέα / νέο = new, young, recent

In many everyday situations, καινούρια δουλειά sounds very natural for new job.

Also, you may see both spellings:

• καινούρια
• καινούργια

They are both standard and mean the same thing.

In Modern Greek, the preposition σε takes the accusative case.

That is why you get:

• στη δουλειά
• στην καινούρια δουλειά

Even though English says in the new job, Greek uses σε + accusative for this kind of location.

So grammatically:

• dictionary form: δουλειά
• accusative singular: δουλειά
• article in accusative feminine singular: τη(ν)

This is why you see στην καινούρια δουλειά.

δεν is the standard negation word used before verbs in Modern Greek.

So:

• ξέρω = I know
• δεν ξέρω = I don’t know

Greek normally puts δεν directly before the verb it negates.

Examples:

• Ξέρω. = I know.
• Δεν ξέρω. = I don’t know.

So in the sentence, δεν ξέρω αν... means I don’t know whether/if...

Here αν means whether / if in an indirect question.

So:

• Δεν ξέρω αν πρέπει... = I don’t know if/whether I should...

In English, if and whether are both possible here.
In Greek, αν is the normal word used in this structure.

It does not mean a condition here like If it rains, I’ll stay home.
Instead, it introduces the thing the speaker is unsure about.

Because πρέπει is followed by να + verb.

This is a very common Greek pattern:

• πρέπει να πάω = I must / should go
• πρέπει να δουλέψω = I must / should work
• πρέπει να φοράω = I should / am supposed to wear

So:

• πρέπει = it is necessary / one must / should
• να φοράω = to be wearing / to wear

Greek does not say πρέπει φοράω in standard grammar. The να is required.

This is a very important Greek verb-aspect question.

Greek often chooses between:

• imperfective: φοράω
• perfective: φορέσω

Here, φοράω is used because the sentence is talking about a repeated or ongoing situation at work: what one is supposed to wear in general.

So the meaning is:

• πρέπει να φοράω στολή = I should be wearing a uniform / I’m supposed to wear a uniform

This is about a regular dress code, not a one-time act of putting something on.

Compare:

• Πρέπει να φοράω στολή στη δουλειά.
  = I’m supposed to wear a uniform at work.
  (habit / general rule)

• Πρέπει να φορέσω τη στολή τώρα.
  = I have to put on the uniform now.
  (single action)

So φοράω is the natural choice here.

Usually φοράω means wear.

That can be confusing for English speakers, because English distinguishes:

• wear = have clothes on
• put on = the action of dressing

Greek can express both ideas, but context matters.

In this sentence, φοράω clearly means wear:

• να φοράω στολή = to wear a uniform

If you want to emphasize the one-time action put on, Greek often uses the perfective form:

• να φορέσω τη στολή = to put on the uniform

So here the sense is not put on, but wear as part of the job.

Greek often omits the indefinite article where English would use a or no article at all.

So:

• φοράω στολή = wear a uniform / wear uniform
• φοράω απλά ρούχα = wear plain/regular clothes

This sounds natural in Greek.

If you added the article, the meaning would become more specific:

• τη στολή = the uniform (a specific uniform)
• τα ρούχα = the clothes (specific clothes)

But here the speaker is talking generally about dress code, so no article is needed.

In this sentence, στολή definitely means uniform.

It can refer to the standard clothing worn for a job or role, such as:

• a nurse’s uniform
• a police uniform
• a school uniform

In other contexts, it can also mean an outfit associated with a role or function, but here δουλειά makes uniform the obvious meaning.

So:

• να φοράω στολή = to wear a uniform at work

Here απλά means plain / regular / ordinary, not simple in a literal sense.

So:

• στολή ή απλά ρούχα = a uniform or just regular clothes

This can be slightly tricky because απλά can also be an adverb meaning simply / just in other contexts.

But here it agrees with ρούχα:

• ρούχα is neuter plural
• απλά is also neuter plural

So grammatically, απλά is an adjective here: plain/regular clothes.

A natural English translation is often:

• uniform or just regular clothes

ρούχα is the normal everyday Greek word for clothes.

It is:

• ρούχο = garment / item of clothing
• ρούχα = clothes

Greek often uses the plural here, just like English does with clothes.

So:

• φοράω ρούχα = wear clothes
• απλά ρούχα = regular/plain clothes

If you want to say clothing in a more general or formal sense, Greek has other options, but ρούχα is the natural everyday word.

Yes, Greek word order is fairly flexible.

Starting with Στην καινούρια δουλειά puts the setting first:

• At my new job / In the new job, I don’t know...

This is natural because it introduces the context before the main statement.

You could also say something like:

• Δεν ξέρω αν στην καινούρια δουλειά πρέπει να φοράω στολή ή απλά ρούχα.

That is also correct, but it sounds a little different in emphasis.
The original version foregrounds the new job first.

So the sentence starts with the context, then gives the speaker’s uncertainty.

It can mean both job and work, depending on context.

Here, στην καινούρια δουλειά is best understood as:

• at/in the new job
• in my new job

That is because the sentence is about workplace clothing rules.

But in other contexts, δουλειά can also mean work more generally:

• Έχω πολλή δουλειά. = I have a lot of work.

So this is a very useful word, but context decides whether job or work is the better English translation.

Yes, you could.

Both of these are natural:

• στη νέα δουλειά
• στην καινούρια δουλειά

The difference is small in many everyday contexts.
Very roughly:

• νέα can mean new / recent
• καινούρια often feels more like new, not old, newly acquired

For new job, both are common and understandable.
The sentence uses καινούρια, which sounds very natural and everyday.

A natural rhythm would usually stress the important content words:

Στην καινούρια δουλειά δεν ξέρω αν πρέπει να φοράω στολή ή απλά ρούχα.

Typical stress focus might fall on:

• καινούρια
• ξέρω
• πρέπει
• φοράω
• στολή
• ρούχα

If the speaker is contrasting the two clothing options, they may especially stress:

• στολή ή απλά ρούχα

So it may sound like:

• ...να φοράω στολή ή απλά ρούχα;

That helps express the uncertainty between the two possibilities.