ONE: Awake the Creative Part of Your Mind
Getting dressed should be a creative process to wake your mind up. In order to do this, you'll have to channel that creative part of your mind, the part where those brilliant ideas and thoughts come from. The more you practice getting dressed creatively, the easier it will be to conjure up clever outfits. If you're pairing your usual pieces together, you're doing it wrong.
TWO: Experiment with Style
You should be experimenting and discovering what works and what doesn't within the realm of your clothes. It's amazing how "new" your old clothes can look with a bit of fresh styling! When dressing, we tend to fall into patterns by wearing what we've already discovered to look good together, we wake up with a general idea of what our outfit will look like or consist of, instead of visualizing the pieces you have to work with individually and then styling them with others.
THREE: Dress with a Purpose
When getting dressed, always keep in mind the day's activities before you. Dress yourself according to whatever you plan to do that day, even if you still have yet to figure what that may be.
FOUR: Dress for Yourself
This may seem like a simple, useless tip, but often when I'm creative-dressing, I get carried away and turn into style-editor-curating-an-editorial-mode instead of, well, myself. Remember your personal style and who you are.
FIVE: No Outfit Is Set in Stone, nor Should They Be
Just because you made a perfect, sartorial discovery doesn't mean you can't wear it again. (It also doesn't mean that you should keep wearing the exact same outfit again and again. Moderation is key.) It'll take many tries to get that perfect outfit (sometimes we're just an accessory away from that Sartorialist-worthy look), but once you find it you should still be tweaking it nonstop. Style isn't wearing the same thing over and over, it's pushing yourself to look better than you did before.
All photos via Pinterest.