first sim does not save

I'm jumping in just to make sure you understand this fully.

These are the categories your Sim needs outfits in. They are not categories you choose from to pick just 1 outfit from.

Your Sim needs one (or more) outfit(s):

Everyday: for every day, their normal outfit(s)

Formal: for events that need formal attire

Athletic: for when they work out

Sleep: for when they go to bed
Party: an nice outfit for parties

Swimwear: a bathing suit to swim in
Hot weather: for when it's hot outside and they need something a bit shorter than normal

Cold weater: for when it's cold outside and they don't want to freeze to death. 

You need to pick one or more outfits in these categories. Your Sim wil automatically switch between the outfit they need. So if you'd sent your current Sim to the pool they'll switch from what they are wearing in to swimwear by themselves, you don't have to do this for them.

The closet is to pick something new, if the outfits you currently have don't fit your Sims style any more or if they just need a new look.

To add, what you see happening on that picture at the end when you hit the check mark. Your Sims are wearing all everyday outfits, that's how it's intended to be. If you want them to wear something different you'll have to select that outfit in everyday.