I've always found the best photos come when you shoot with a friend. Where he/she expands his/her craft, and you have a chance to just be you.
It's not about having a great camera, a crisply focused photo, the best pose, a perfect outfit... it's about you being you, the photographer being him/her, and letting that shine.
Outdoors is my favorite place to shoot. Natural light makes you glow (plan for sunrise or sunset for best light). I also find you can relax so much more outside than when you're sitting in a studio.
What you wear, your makeup, your hair... stop stressing about it. Wear something you feel good in, don't change your make-up routine just for a shoot (unless you're doing something really artsy), and pick a hair style that will last for hours. You want to know why a lot of my shots have my hair half back? If I leave it down, it goes flat instantly.
But most importantly, choose a photographer who you feel comfortable with, not intimidated by. This is the most important part. If someone is giving you too much direction or has unreasonable expectations... you won't look like you in the photos.
And getting great shots that represent YOU is the most important part.
Almost my entire Instagram page is filled with shots from a friend snapping a pictures in portrait mode on an Apple phone. It doesn't have to be a fancy, formal thing.
Like this! I wore this little black Caara dress to work, the same day my co-worker, Nay Renee brought her camera. The result? A really great time with some lovely prints to show for it.
Bonus Shot: Me and Marcel. My go-to digital / social media consultant.