In my dating “career” I’ve really seen it all. When it comes to dressing up for a first date, some people aren’t really sure what they are doing.
I’ve seen guys dressed in grubby t-shirts and jeans. I’ve been surprised to see dress clothes and shoes on a guy, when he was the one who planned our outdoor date that got him all dirty. Probably the worst I’ve seen is when it’s obvious the guy didn’t even take a shower!
Come on, really?
When it comes to a first date, you’re really out to impress the other person. The ultimate goal is to find someone you you love, who can lounge around at home with and be yourself–but that is for later. Much, much later. Your first date is when you put your best foot forward. That means dressing for success.
So a little common sense here. These are the non-negotiable rules:
Take a shower that same day. Wear clothes that have been washed and not worn yet since they have been washed. Pick something that doesn’t have stains, holes, and covers most of your body. Wear clothes that actually fit you–nothing too baggy or too tight. Easy, right?
I’m not saying you have to run out and buy something new. The point is to be clean and respectful, and to show your date you put at least a little thought into it.
Now that we have that out of the way, it’s time to be more specific about what you should wear on a first date. I want to help you pick out something that will help you do a few things:
- Impress Your Date/Be Flattering
- Help You Feel Comfortable
- Be Appropriate for Your Activity
So let’s go through these one at a time.
Impress Your Date/Be Flattering
Think about your date. Is this a casual person, or someone who likes to dress up? It’s important to try to dress within a similar realm so you look like you sort of fit together on this date. It’s ok if you don’t dress similarly all the time, but on a first date it’s best to lean a little towards what your date might wear. If she loves to wear dresses, then wear a dress shirt with jeans. You’ll always be safe there. You can dress it up with a tie or dress it down byt unbuttoning the top two buttons and rolling up the sleeves. Very sexy, and very classy.
The other consideration is to pick clothes that are flattering on you. Grab a few shirts of varying colors and hold them up to your face while standing in front of a mirror. Which colors look best with your skin tone? This isn’t rocket science–just go with your gut reaction here. If you don’t like bright colors, then don’t wear them. Some people just look better in more muted tones. Each person is different! If you aren’t sure whether to choose a pattern or a solid, the safe bet is always the solid. Also, find cuts/shapes of clothes that are flattering. For example, a woman who picks out a shapeless cotton shirt may end up looking boxy and less feminine. It’s better to wear something that has some shape to it so it can accentuate her curves.
Help You Feel Comfortable
The most important thing on a date is to be yourself, and the best way to do that is to be comfortable. But please realize that while jammies are really comfortable, there are a lot of really nice clothes out there that are surprisingly comfortable! Some sleek dress pants can feel just as comfy as your lounge wear. Even a nice, fitted shirt can feel almost like second skin. The important thing is to find clothes that are well constructed and are made of good material. Try on lots of things and find what you like!
The other consideration with comfort is what fits your personality. Maybe you’re a more casual guy who works with his hands for a living. If you usually wear grubby t-shirts and jeans most of the time, then you only really need to step it up a touch for a first date. Find a clean, solid colored, clean t-shirt, and get your best pair of clean, non-holey jeans. Wasn’t that easy? You’ll be a little more dressy than usual your usual self, but not so far away from the norm for you to feel uncomfortable.
Be Appropriate for Your Activity
When picking out which clothes to wear, one of the biggest considerations is– what will you be doing? If you are going on a hike, then dress for it! Wear hiking shoes, and maybe an extra layer of clothes in case it gets cold. You can be less dressed up for this type of activity, but your clothes should still be clean, unwrinkled, and classy looking.
If you are going dancing, to a play, or to a nice restaurant, then you’ll need to dress up quite a bit, and wear dressy but still comfortable shoes. The key is to think ahead. What would other people wear in those situations?
If you are still feeling lost about what to wear, then ask your sister, brother, cousin, or best guy or girl friend for some advice. He or she may even come over and help you get ready!