I rarely seem to plan my outfits anymore.
Texas weather is very bi-polar so waiting until the day of is usually my best bet. Shoes are usually the first thing I think about when planning an outfit. I'm sure that sounds a little crazy, but here's my logic...
Picking my shoes first keeps me from wasting time choosing an outfit that requires shoes that may not be ideal for that day.
Next, I decide what mood I'm in...dress/skirt, jeans, or trousers. After that I choose my layering pieces (cardigan, scarf, blazer, etc.)
Honestly this process usually takes me about 10 mins. I just use my imagination and go. And once you have your closet memorized outfits naturally pop up in your head. It also helps to think of past outfits you've made and find ways mix and match that outfit with current items in your closet.
I have heard people use the term "I don't have any fashion sense." I don't feel like that's true.
I feel like we all do. We're all unique and "create" our own outfits everyday (even if those outfits seem plain to us). When I get dressed each day I base my outfit on how I'm feeling that morning.
I "wear" my attitude. Now we've all had those days where we just couldn't seem to get it together. Rushing to work, late for an engagement, or simply just stood in front of our closet with a blank stare. The more you get to know your style the easier it will be to find an outfit in a hurry for any occasion.
Experiment until you find exactly what you like and what works for you.
Play with patterns. Everything isn't set in stone.
Don’t concentrate so much on matching. Play with colors and see what you come up with.
Don’t be afraid to try something new. If you like it, rock it.
* A particular must have for me in my closet is brown and nude color pieces (footware, layering pieces, scarves, etc.). They can be paired with just about anything.
Example of a quick outfit I would put together:
Shirt: H&M (photo linked with similar product)
Jeans: Unknown (photo linked with similar product)
Heels: Charlotte Russe (photo linked with product)
Bag: H&M (photo linked with product)
In a Nutshell
Ultimately, have fun with your creations. The more you do it the more naturally it will flow.