Everybody does it differently and Angie is okay with any way we decide to "play" as long as we play nice!
If you just want to keep yourself accountable and don't want feedback on specifics, you can always post your WIWs in batches. Sveta likes to do a weeks' worth of looks at one time. Kellygirl usually posts 3 or 4 outfits at once. Amiable sometimes does it that way, too. This is especially useful if you are short on time.
But Mary and Shannon and others like to post once a day whether they need help with an outfit or not -- and that is equally good!
Some people post daily. Some post monthly. Some post when they have a special occasion only. Some post a whole lot one month, and nothing for the next two. It's all good.
If I'm wearing one of Angie's ensembles, I'll usually post it as a separate post because it's fun for everyone to see. I also post more regularly if I'm following a challenge (sometimes separate day by day posts, and sometimes in a batch after a while). And sometimes I'll post an outfit for no reason at all other than I feel like it!
If I really want help deciding between alternatives, or figuring out what's not working for me, or trying to decide if something is a good purchase for me, I like to post a separate thread, because this way I can ask directly for feedback and it won't get lost in a lot of other verbiage (or imagery).