Even though it’s technically Fall, there are many of us who are enjoying Indian Summer evenings.  So, what do you wear when you are meeting a guy you really like for your “first” date?

Reader question of the week:

I’m petite, 5′0″ and am going to the park with a gentleman that I’ve met one time and have talked on the phone with on a number of occasions.

I want to look nice, but not overdone for a casual night out!  Since I’m short, I don’t want to chop off my legs by wearing capris, however, I’m at a loss!!  I really want to make a nice impression…..HELP!!

Wardrobe 911’s Style Prescription:

‘Appropriate’ takes on a whole new meaning with first-date jitters! On warm evenings, you want to be cool and comfortable so a dress is in order.  By selecting a fabric such as cotton, you are immediately communicating casual.  So, a cotton dress is nice but not over-the-top for a casual night out. You want the skirt of the dress to hit right below the knee and since this one comes in petite, you won’t have to worry about getting it hemmed.  Pick a color that matches one of the colors in your eyes and you’ll have him at hello.

For accessories, wear some feminine jewelry — I absolutely adore this enamel ring from J.Crew.  The Coach bag is casual and chic.  Gain some height with this cute wedge sandal by Natural Comfort, which by its name should be so comfortable you could run in them.

And in case he turns out to be a loser, remember that you can use your bag as a weapon and run like hell, stylishly.