What to wear on a first date

Oh, the woes of a first date. Or, maybe you are super excited? Maybe it’s someone you’ve chatted with online, exchanged a few emails, or perhaps you met on the street. Do people still meet on the street? Well, however you met, you still might have struggled with what to wear on a first date.


A few simple rules that I like to stick by. Think about how you met this person. Was it in a dark bar where you were heavily made up, or did you meet him wearing no make-up and yoga pants? How about that spread of online photos where you put your best face forward? The point is, you don’t want any shock value. What’s the season? Is it 56 degrees outside and you show up in a halter top and a mini? Don’t make weird decisions like that. Conversely, don’t wear your bulkiest knit when it’s sweltering outside. Also, dress for the occasion. If it’s a picnic, don’t wear your prom dress. If it’s a hike, don’t show up in your sexy wedges that you have tried to pass off as your most comfortable shoes. You will be miserable. I think you get the message.

I’ll start with make-up.  I’ve never met a guy in my life who liked a chick with heavy dark eye shadow, sticky lipsticks and loads of foundation. If you have a tendency to wear a lot to begin with, do your best to make it subtle. I’m talking to redheads here. Don’t cover those cute sprinkle of freckles across your nose, but do play up your eyes, and wear mascara, because it will make you feel good and give you confidence. Plus, it plays up that feminine thing. If you are meeting at night, you can wear a little more make-up than you would in the daylight, but remember, if you are drawing out the features of your lips, for example, go easy on the eye make up. Draw attention to your favorite features but don’t overdo it.


For what to wear, I like to play up my assets. Have great legs? Show them off, but do it in an elegant way. Playing up your assets will make you feel sexy and pretty. I like choosing soft fabrics, material that clings in some places and not in others. A backless sweater for instance, or if you are wearing jeans, a soft silky top with a great pair of heels.

Remember, you can never please everyone so choose something that stays true to your fashion sense. And if all else fails, and if the occasion calls for it, break out the t-shirt and jeans, tousle your hair, wear an adorable short jacket, red lipstick and heels. No one will be too disappointed with that.

Hair? I think most people like to see your hair down, in its natural flowing state. Hair is powerful, and red hair makes even more of a statement, so make the hairstyle decision based on what your outfit is. I love this photo below because she is dressed casually, but totally sexy with earthy tones. She also happens to be wearing one of my favorite colors, hunter green. She goes a little heavier on the eyes, which is ok since her outfit is subtle enough. It just works.