First Date Fashion - Dressing for the Occasion

First Date Fashion - Dressing for the Occasion

Whether you’ve been single for awhile or just getting back into the game, a first date is exciting. While you may be anxiously awaiting your night out, you may be getting a little nervous as well. One of the biggest issues for a first day is deciding what to wear. Often times you start planning an outfit days in advance only to find that that you hate what you picked out. If spending hours in front of the mirror deciding between a skirt and pants, heels and flats, and black and blue, is not your idea of a good time, you’re not alone. Here are some tips to help you decide how to dress as well as how to do your hair and makeup for different types of dates.

What to Wear:

  • Daytime Date: If you’re going to be going on a day time date, consider wearing something a little more casual. Often times day time dates are meant to ease the nerves and hang out without the possibility of commitment looming over your head. Choose something that’s fun and slightly flirty, but remember to stay practical.
  • Out Door Dates: Going on a date that takes place outside or involves a lot of walking means you’ll need to dress appropriately. Even though you may love your brand new ruby red heels, you may want to save them for a dinner date. Wear flats that won’t get stuck in the grass and will keep your feet comfy when walking long distances.
  • Casual Nighttime Dates: Casual dinner and a movie dates generally call for something a little dressier than your day time attire; however, they don’t require your little black dress. Choose a pair of dress pants or a skirt and heels with a fun and flirty shirt. If you want to wear jeans, stay away from ones that are ripped or faded and opt for a darker color designer jean.
  • Elegant Evening Dates: Sometimes men feel it necessary to pull all the stops and take you to a fancy restaurant on your first date. If this is the case, clearly your possible new beau wants to impress you, so humor and respect him by dressing for the occasion. This is when you pull out the little black dress or a colorful equivalent and a pair of great heels. Don’t disappoint him when he picks you up by wearing jeans, even if they are really sexy.


  • Daytime Dates: For a casual day date, you can basically wear your hair any way you feel comfortable. If you want to dress it up a bit, try adding a cute head band or scarf that matches your outfit. Regardless of where you’re going, make sure your hair it neat and clean. You may not want to act like your desperate, but doesn’t look like you’re not trying at all.
  • Out Door Dates: If you will be outside for the majority of your date or if you’ll be walking to and from different places, you may want to consider pulling your hair back. This will save you the awkward embarrassment of having your perfect hair-do turn into a hair disaster because of wind, a game of soccer, of an unfortunate rain storm. Again, accessorizing your hair is a great way to turn an everyday pony tail into a cute date appropriate up do.
  • Casual Nighttime Dates: Casual dinner and movie dates are a great opportunity to wear your hair down and take some more time in deciding how to style it. Chances are you won’t be outdoors for long, and you won’t be taking part in physically taxing activities (at least not early in the night!). If you look great with your hair down and curly or have short hair that looks great in sassy, spiky styles, go for it. The goal is to be comfortable yet polished.
  • Elegant Evening Dates: If you will be dining at an elegant restaurant definitely put some time and effort into your hair. This is when you’ll want to ensure that every piece is in its right place. Often times an up-do is a great way to keep control of your hair while looking stylish and sophisticated. You’ll want to keep your accessories to a minimum. Instead of that cute scarf that you like so much, try going with small decorative barrettes to add a little refined dimension.


  • Daytime Dates: Keep your makeup to a minimum. Unless you always wear a ton of makeup, don’t overdo it for a day date where you’re most likely going to be in brightly lit places. Save the smoky eyes and blood red lipstick for a special night time occasion.
  • Out Door Dates: Keep in mind that outdoor dates may be more physically taxing. Going for a walk; running around, or being out in the elements can easily turn pretty eyelashes into embarrassing black streaks running down your cheeks. Choose makeup that will stay on and won’t smudge. Again, you’ll want to stay away from tons of eye makeup and bold lip sticks. The goal here is to go for look playful not like a diva.
  • Casual Nighttime Dates: When applying your makeup, you can be more liberal for evening dates than you are for daytime engagements. This means you can break out the eye liner and go a little darker with your lipstick and eye shadow. Even though you’re going out during the evening, don’t overdo it.
  • Elegant Evening Dates: While you should pay particular attention to your makeup, you still want to keep in mind that less often more. You may not want to go overboard if you’re going to a classy dining establishment. Often times men enjoy woman who keep their makeup natural and most men will appreciate this if they are taking you somewhere where sophistication is the key. Subtle eye shadows and lip glosses with a bit a shimmer are a great option for elegant dining.

write by Joshua Olin