A ottobre porto una sciarpa leggera la sera.

Here a ottobre means in October.

With months, Italian often uses a where English uses in:

• a ottobre = in October
• a maggio = in May
• a dicembre = in December

So this is a normal time expression. You should not translate a too literally as only at.

In Italian, month names usually appear without an article when you are simply stating when something happens:

• a ottobre
• in ottobre
• ottobre è freddo

You might see an article in other contexts, but in a basic time expression like this, ottobre normally stands alone.

Here porto means I wear.

The verb portare can mean several things depending on context, including:

• to bring / to carry
• to wear

With clothes or accessories, portare often means to wear:

• porto una giacca = I wear a jacket
• porta gli occhiali = he/she wears glasses

So in this sentence, porto una sciarpa leggera means I wear a light scarf.

Both can work, but they are not exactly the same in feel.

• porto una sciarpa = I wear a scarf
• indosso una sciarpa = I am wearing / I wear a scarf

Indossare is more specifically about wearing clothing or accessories.
Portare is broader and very common in everyday Italian, especially with things like:

• portare una sciarpa
• portare gli occhiali
• portare i capelli lunghi

So porto is completely natural here.

In Italian, adjectives usually come after the noun, especially when they describe a straightforward quality.

So:

• una sciarpa leggera = a light scarf

This is the most neutral and natural order.

Putting the adjective before the noun is sometimes possible, but it often sounds more literary, emphatic, or stylistically marked. For an ordinary sentence, sciarpa leggera is the standard choice.

Because sciarpa is feminine singular, the adjective must agree with it.

• una sciarpa → feminine singular
• leggera → feminine singular form of leggero

Agreement pattern:

• leggero = masculine singular
• leggera = feminine singular
• leggeri = masculine plural
• leggere = feminine plural

So una sciarpa leggera is correct.

La sera here means in the evening.

Italian often uses the definite article in time expressions of this kind:

• la mattina = in the morning
• il pomeriggio = in the afternoon
• la sera = in the evening

So even though English says in the evening, Italian can simply say la sera.

Yes. Di sera is also possible.

Both can mean in the evening, but there can be a small difference in feel:

• la sera often points to the evening / in the evenings
• di sera often sounds a bit more like in the evening / during the evening time

In many everyday contexts, both are fine. In this sentence, la sera sounds very natural.

Because they answer two different time questions:

• a ottobre = when in the year?
• la sera = when in the day?

So the sentence gives a broader time frame and then a more specific one:

• In October
• in the evening

This is very normal in Italian.

Yes. Italian uses the present tense very often for habits, routines, and things that are generally true.

So porto here means something like:

• I wear
• I tend to wear
• I wear habitually

It does not have to mean only right now at this moment.

Yes. Italian word order is flexible, although some versions sound more neutral than others.

The original sentence:

• A ottobre porto una sciarpa leggera la sera.

Other possible orders include:

• La sera, a ottobre, porto una sciarpa leggera.
• Porto una sciarpa leggera la sera, a ottobre.
• A ottobre, la sera, porto una sciarpa leggera.

The original order is natural and clear: it gives the general time first, then the action, then the more specific time.

No, not normally.

• A ottobre porto una sciarpa leggera la sera.

This is perfectly correct without a comma.

You could add a comma for pause or emphasis in some contexts:

• A ottobre, porto una sciarpa leggera la sera.

But in a simple neutral sentence, Italian usually leaves it out.