"Is Mr. Sun out? Is it gloomy? Will it rain later?" Well let me introduce you to my dear friend, The Weather App. Most smartphones come with their own weather applications and I think they are being underused. Now you have all the reason to use this app to plan your outfit for the day.
This is another important thing to consider. If you're hitting the beach for a vacation, you don't want to be caught wearing your sweater and pants. So you have to know the place you're going to so you could wear a suitable outfit.
The last thing you have to consider is your situation. For example, if you are going to a casual party make sure to wear casual party appropriate clothes. Jean shorts and T-shirt don't make the cut; There's still a "party" word next to casual. So let's say you are going to the mall to shop. As much as you want to look cute, stylish, and put-together, those heels will not do you any good. Instead, wear your cutest sandals and trust me you would be just as stylish as you wish to be when you're in heels!
Top from Willow by Chang, Pants from Topshop, Heels from Aldo