Ah, the always unnerving ‘what to wear on a date’ scenario. It’s hard trying to blend what makes you feel comfortable with the expected dress code of the venue you’re about enter. That’s without even trying to factor in what “he” will be wearing.
Let’s first start of by saying, you want to make sure that whatever you wear, you feel comfortable. This will ensure that you won’t be focusing on other things such as how uncomfortable and awkward you feel, because this will translate in your body language. This is sound advice for any date really.
More importantly, keep things simple! You don’t want to be wearing anything too outlandish, outrageous and attention grabbing for two reasons: one, by toning things down and dressing in a simple classic manner it brings your personality to the forefront – you’re a lady that’s wearing the clothes, not the other way around.
Other than that, it’s about dressing for the situation:
The Fancy Date
I.e. one that has required a reservation to be made at least a couple of months in advance. This is normally at a restaurant, with the possibility of heading to a fancy bar for a few drinks after.
In this situation, opt for your favorite leather jacket, a nice piece of jewelry, and a heel that you will feel comfortable in, otherwise, the combination of a formal date, a dress code–necessary restaurant, and an overly sexy dress could potentially freak you out so much that you lose your cool. It’s a good idea to go hands-free where your handbag is concerned—forgoing a fussy evening clutch will put you at ease. You can use the pockets of your leather jacket instead of a bag. Plus, it adds a little down-to-earth edge and balance to the femininity of the dress.
The Cinema Date
Dress casually for a date to the movies. Choose garments that are dressy but not too formal, such as an outfit you’d wear to the office. Do not wear a T-shirt and jeans, looking like you put forth little to no effort for the date. Also plan for what you and your date will do before or after the movie, such as dining at an upscale restaurant or taking a leisurely walk through a park, as that activity will also dictate what you should wear. Try opting for a blouse and add a blazer to dress up your outfit giving you something to slip on if you get too cold in theater. Match the blouse and blazer with a pair of dressy jeans, leggings or a skirt. And for obvious reasons, don’t wear a skirt that is so short that it’s uncomfortable sitting down or gives the wrong idea.
A Night-in/Home Cooked Meal
This could be at yours or his but either way the dress code is the same – whatever you normally wear there. With the exception of sweats and hoodies, because it’s still a date remember. Try dressing up jeans with cute boots or booties and a leather jacket, something comfortable but still cool.