Hello Sweetheart, Would You Like to Play Barbies? - Babyzilla to a 20 something salesman

A good sense of humor can get you through just about anything, like a sprained ankle and being carted around the mall in a wet diaper.
A good sense of humor does not a good wardrobe make. For that you need good judgment. The key to dressing well is keeping cuts and colors classic. You can throw in a fun touch here and there so long as it doesn't come off looking juvenile. Take it from me, I spent way too many years shopping in the Junior department.
Start with a good haircut. Consider it your investment in you. A good haircut is not necessarily one cut by a professional. The "moment's" hair is edgy and looks like you might have taken scissors to yourself, ergo my new "do". It has a youthful quality, but is serious. Ask your hairdresser to cut like an amateur. That way you won't walk around looking like a hollywood wannabe. You might even look healthier, which wouldn't be such a bad thing for most of us.
The next step is throwing out all clothing and accessories that a twelve year old might wear, unless you're twelve. No more outings in pajamas, save those for the bedroom. When you look at your wardrobe, it should be "ageless". Any item in your wardrobe should look good on a person of any age. If that neon orange sweater would only look good on your dog, toss it.
This includes "funny" shirts, jewelry, shoes, hats, hair ribbons, ect., unless you want to join the circus.
Speaking of circus, ignore the red lipstick trend. Red lipstick only looks good on a few flawless faces. On most people it instantly transforms them into Ronald McDonald. Make-up is an art, so a trip to your local department store cosmetics counter for some tips might be in order. For the price of an eyeshadow or a lipstick, you could get some solid advice.
Be yourself. If you don't feel comfortable in the latest trend, then skip it. Most people "overdo" it anyway. All of the third world countries could probably be clothed in what we have and really don't need. And all of that fashion is really a distraction, for the most part. What you really want people to see is a healthy, glowing you. Try shutting off the t.v., turn on some good music instead and dance around. Take that walk to the neighborhood store instead of hopping in the car. Drink real orange juice instead of grabbing a soda. The world will see a happier, stronger you.
*The fashion in this article is from Old Navy.