Will you please help me find my perfect lipstick color?

I recently read this article talking about how women should know which lipsticks work for them by the age 30. Oops. I guess I missed that ‘something you’re supposed to do in your 20’s’ memo. I’m going to be 35 this January and I still haven’t really gotten my proverbial feet wet in the world of lipsticks.

I’ve always been more of a gloss girl. I tend to choose more neutral, slightly pinky glosses. There was a brief period, post college, circa 2003, when I tested the waters with some dark berry tones, which are apparently back in style, but it’s been at least 10 years since I’ve seriously worn lipstick.

Since then, I’ve only worn lipsticks on very particular occasions—for photo shoots back in my modeling days, and for Halloween costumes.The makeup artists I worked with would always put me in berry tones and I always felt self conscious with dark lipstick, even though it photographed well. For Halloween, I remember using a vibrant red color when I was a ladybug and a near-black color when I was an (embarrassing) dominatrix.Besides these rare occasions, I’ve never gotten around to really figuring out which lipsticks work for me like I’ve done with every other area of makeup (blush, concealer, BB cream, eyebrow shapers).

I decided it’s finally time to figure it out, so my good friend, and occasional makeup artist, Caitlin, agreed to let me borrow her collection of lipsticks. She had several different applicator styles and in various consistencies, but I decided to only try traditional lipsticks, save for one lipstick pencil. That meant I got to try 15 different colors of lipstick, which was a bit overwhelming.

Since I’m a novice lipstick wearer, I wanted to ask you for your input. I can’t decide which colors look best on me, so I want your help deciding. Will you please help me find my perfect lipstick color?

1. Korres Mango Butter Lipstick – Rose 22
2. Tarte Amazonian Butter Lipstick – Pink Peony
3. Benefit Full Finish Lipstick – Lady’s Choice Lana
4. Makeup Forever Rouge Artist Natural– N9 Copper Pink
5. Korres Mango Butter – Peach 18
6. Chanel Rouge Coco– Rouge Captif – Coco Peach
7. Chanel Rouge Coco – Coco Pink
8. Nars Velvet Matte Lip Pencil – Cruella
9. Sephora – Color Lip Last – N3
10. Sephora Collection Rouge Cream Lipstick – R21
11. Sephora Collection Rouge Cream Lipstick – R17
12. Sephora Collection Rouge Cream Lipstick – R19
13. Sephora Collection Rouge Cream Lipstick – R15
14. Sephora Collection Color Lip Last – N21
15. Sephora Collection Color Lip Last – N16

To be frank, lipsticks still feel really strange on me. I was shocked by how bright nearly every color felt on me, except for those colors that are very similar to my natural lip color. I remember reading somewhere that you just have to dive in and wear a bright color for a couple days to get used to it. I’m willing to give it a shot, but I need your help.

Which color do you like best on me? Which color should I add to my regular makeup arsenal? Which brand or color didn’t I included that  you think I should try?

As a thank you for helping me out, those who leave a comment will be entered for a chance to win a $25 Sephora gift card.* Thank you!

* To be eligible, leave a comment by 11:59pm PDT on Friday, October 17th. Must be 18 or over. Open to U.S. residents only. Winner will be randomly chosen from all eligible entries and will be contacted within two business days.