No me gusta llevar mucho maquillaje cuando hace calor, pero sí me pongo pintalabios para salir a cenar.

After gustar, Spanish normally uses an infinitive when you are talking about liking or not liking an action.

So:

• Me gusta llevar maquillaje = I like wearing makeup
• No me gusta llevar maquillaje = I don’t like wearing makeup

Using llevo would be incorrect here, because llevo is a conjugated verb (I wear / I carry), and after gusta you need either:

• a noun: Me gusta el maquillaje
• or an infinitive: Me gusta llevar maquillaje

Llevar has several meanings, and one very common one is to wear.

In this sentence, llevar mucho maquillaje means to wear a lot of makeup.

Some common uses of llevar are:

• llevar una mochila = to carry a backpack
• llevar gafas = to wear glasses
• llevar maquillaje = to wear makeup

So yes, llevar can mean to carry, but with clothes, accessories, glasses, perfume, makeup, etc., it often means to wear.

Because maquillaje here is being treated as an uncountable noun, like makeup in English.

So Spanish says:

• mucho maquillaje = a lot of makeup

not normally:

• muchos maquillajes

You only use a plural like maquillajes in more specific contexts, for example when talking about different kinds or styles of makeup.

In everyday speech, maquillaje usually works like a mass noun:

• Lleva poco maquillaje
• No uso mucho maquillaje

Spanish uses hacer in weather expressions like this.

• hace calor = it’s hot / the weather is hot
• hace frío = it’s cold
• hace buen tiempo = the weather is nice
• hace mal tiempo = the weather is bad

So cuando hace calor literally looks like when it makes heat, but in natural English it means when it’s hot.

This is just a standard Spanish structure you need to learn as a fixed expression.

Here sí adds emphasis and contrast.

The sentence contrasts two ideas:

• No me gusta llevar mucho maquillaje cuando hace calor
• pero sí me pongo pintalabios para salir a cenar

So pero sí means something like:

• but I do put on lipstick
• but I do wear lipstick
• but I will wear lipstick

It stresses that although the speaker does not like wearing much makeup in hot weather, there is one thing they still do.

This sí is not the word for yes in a simple answer. Here it is an emphatic adverb used to reinforce the contrast.

Because ponerse is the normal verb for putting something on yourself.

• poner = to put
• ponerse = to put on oneself / to put on

So:

• Me pongo pintalabios = I put on lipstick
• Me pongo una chaqueta = I put on a jacket

Without me, pongo would usually suggest putting something somewhere, not applying or wearing it yourself.

For personal appearance, Spanish often uses reflexive forms:

• me pongo maquillaje
• me pongo crema
• me pongo perfume
• me pongo un vestido

With products like makeup, perfume, or clothing, Spanish often leaves out the article when speaking generally.

So:

• me pongo pintalabios = I put on lipstick

This sounds natural when the speaker means lipstick in general, not one specific item.

You could say un pintalabios, but that would sound more like a lipstick product / one lipstick as an object. For example:

• Me compré un pintalabios rojo = I bought a red lipstick

Similarly:

• llevo maquillaje = I’m wearing makeup
• me pongo perfume = I put on perfume

No article is very common when talking about applying or wearing something in a general sense.

Yes, pintalabios is a very normal word in Spain for lipstick.

It literally breaks down as:

• pinta- from pintar = to paint
• labios = lips

So it is literally something like lip-paint.

In other Spanish-speaking countries, you may also hear:

• labial
• barra de labios

In Spain, pintalabios is very common and natural.

Yes, both relate to makeup, but they focus on slightly different things.

• llevar maquillaje focuses on wearing makeup in general
• ponerse pintalabios focuses on the action of applying/putting on lipstick

So the sentence is natural because it combines:

1. a general preference: No me gusta llevar mucho maquillaje
2. a specific action or exception: pero sí me pongo pintalabios

You could think of it as:

• I don’t like to wear much makeup...
• but I do put on lipstick...

That contrast is very natural in Spanish.

Because it means in order to go out to dinner.

Break it down:

• para = for / in order to
• salir = to go out
• a cenar = to eat dinner / to have dinner

So:

• salir a cenar = to go out for dinner / to go out to dinner

This structure is very common:

• salir a tomar algo = to go out for a drink / to go out for something
• salir a pasear = to go out for a walk
• ir a comprar = to go to buy / to go shopping

Here a cenar explains the purpose of salir.

Yes, but it would sound a bit different.

• usar maquillaje = to use makeup
• llevar maquillaje = to wear makeup
• ponerse pintalabios = to put on lipstick

All are understandable, but the original sentence sounds more natural because:

• llevar maquillaje is very idiomatic for wearing makeup
• ponerse pintalabios is very idiomatic for putting lipstick on

Usar is possible, but it can sound slightly more neutral or less idiomatic in this context, especially in Spain.

It is understood everywhere, but it does have a slight Spain feel, mainly because of pintalabios.

The rest is very general Spanish:

• No me gusta...
• cuando hace calor
• para salir a cenar

Those are standard everywhere.

What may vary by region is mainly the word for lipstick:

• Spain: pintalabios
• many Latin American countries: labial is also very common

So the sentence is broadly universal, but the vocabulary choice suggests Spain quite naturally.