Ask your date about the event: Will you need park clothes, beachwear, an urban dinner outfit or rock-climbing gear?
Aim for middle ground for date one. Neutral colors, classic styles and great accessories are always comfortable, especially if you don't know your destination.
Assess your position. Will you convey "career," "artistic," "dynamite" or "easy confidence"?
Decide what makes you feel pretty, sexy, confident or comfortable. Do you want to be more sexy than sedate, or do you want to look sophisticated?
Choose your colors. That little black dress, silver jewelry and an exotic shawl could be stylish and sophisticated. Pastels, gingham or soft lines suggest softness. Tie-dye can be fun or whimsical.
Be yourself. If you're at ease with lower necklines and revealing clothes, go for it if it feels appropriate.
Think comfort. Stiletto heels, new styles or a skimpy skirt may make you uncomfortable and distract you from your date.
Dress it up or down. Classic separates can be easily paired with one extra-special piece for a boost.