I'll give you a few different ideas. For a dressy play and dinner, I personally would go with a simple black pencil skirt. It is perfect for basically every occasion and you won't look overdone, or too casual. Some black peep-toe heels would look great with this, or even a strappy shoe.



Shirt-wise, there are so many options. Call me crazy, but I'm such a huge fan of the whole belted shirt. However, I'd go with a brighter shirt since the skirt and shoes would be black. A nice plum color would be great and it's really big right now. A nice voluminous shirt would look cute too. A fuller skirt would work with all of these as well.

For the more casual date, I don't think there is anything wrong with a nice pair of dark-wash jeans with heels. A nice pair of ballet flats would work too. I love a nice bold sweater. You could add some nice bold silver jewelry to pull it all together. If a sweater seems too hot, go for a fitted 3/4 length top instead.

I am a huge fan of your idea of dark wash jeans and the sweater--personally I'd go with red or another bright color. The ankle boots sound cute. It's probably getting a little chilly for open-toed shoes anyway (I just live on the dangerous side). Any type of heels and jeans just looks so classy in my opinion. The cropped jacket sounds cute, as does the velvet peacoat. The jacket says "I'm such a fun gal!" and the peacoat says "I'm fun but mucho classy!" so it is up to you. Both choices sound great.

This guy sounds great--I'm so excited for you! I love random meeting. I'm sure you'll have a great time.

You asked about where I get my fashion knowledge from and I guess it's a few different things. I have always been a huge fan of "What not to Wear" and other makeover stuff, but recently I've been working at a TV station in Boston helping out the style producer for their fashion segment.

Their's a big difference between a basketball game and the theater, but I'll give it my best shot! You need to wear something classic and versatile so I'm leaning toward nice black pants and a dressiest black sweater...maybe something with a low scoop neck that's fitted with long or 3/4 length sleeves or a black sweater with a v-neck/wrap front. Just not something boxy! You can wear a white or yellow gold necklace...whichever matches your watch and bracelet. Pair the outfit with high heeled black boots and you'll be all set. That's what I would do if I were faced with two such different possibilities!

But don't panic because this is an easy one!!! Wear high heeled brown pumps and a matching brown handbag. The shade of brown is up to you...can be dark or milk chocolate, espresso, a reddish brown, etc. It will all work, but make sure your handbag matches the shoes.

You can wear a great necklace since the neckline is square. Wear yellow gold or natural toned beads, but have the necklace be short so it lays on your chest above the neckline of the dress. You can also wear a gold bracelet and watch. Don't go overboard because the dress sounds classic and your accessories should be as well!