Tory Burch belt, Romwe dress(similar), Chinese Laundry sandals (similar), Anne Klein earring (similar)
Whether your guy is taking you to a nice restaurant or to a fun party, this outfit is simple and sexy but teen approved. You're showing him major confidence by wearing a light blue dress, yet showing sophistication with a cinched waisted belt that will appeal to his mom and yours. Flower earrings are fun and innocent, giving him something to think about when you part ways at the end of the evening.
Chicnova jeans (similar), Sonoma via Kohl's sandals (similar), BCBG necklace (similar), Ruche top (similar), Vera Bradley bag (similar)
Like I mentioned below, confidence is key. All first dates can be kind of awkward, and a necklace with "dream" written on it will give you a topic to chat about when you're both awkwardly sipping water. A bright colored top is appealing to any guy, and will show even more confidence. Since jeans are involved, this outfit is more simple and relaxed, so won't scare any guy away if you're just heading out to a picnic or daytime event.
Holland Rodan rocks this perfect teen date night outfit. The worst impression you can give on a first date is 1) let's skip past the date and forward to where you bring me home + kiss me so I tell all my friends 2) I'm not confident. Guys LOVE confidence. Confidence is a killer trait that everyone of you beautiful girls should have. Opt for a subtle and sexy color (if you have blue eyes, a blue shirt will make your eyes pop, etc) top, and a basic skirt or printed skirt so his eyes stay on you allll night long.
I have had quite the amount of dates lately (with boys, yes, I'm as surprised as you are) and I'm learning what dressing up for a teenage boy is like. Most teenage boys are much more clueless than you, therefore worrying about an appropriate date night outfit should only have one concern: dressing appropriately so your parents don't make you run upstairs and change 5 minutes before the front door is supposed to ring. These outfit ideas are suitable for the most expensive restaurant or the McDonalds one (from personal experience, dump guys who take you to McDonalds on a first date) AND will appeal to the pickiest of rents.