Something that baffles me about the world of women’s fashion is how little voice straight men get. What’s even more ridiculous is that gay men are seen as experts, despite being incapable of having insight into the aesthetics or comfort of women’s clothes. Usually it just means men won’t like how they dress and it’s not a problem, but on a date the exact opposite is true. When you’re on a date, you’re selling yourself, you want him to like you. Obviously, nobody knows better what men like to see than men. I’m going to give you a few points to think about, some tips, and even end off with some suggested outfits. I’ve written about what men like to see but this will be assuming you’re looking to have him be interested in marrying you.
What Has He Told You?
What he’s told you about his plans for your date and his preferences for women’s clothes can tell you a lot. Always dress appropriately for whatever activities he has planned, even if that would go against any of the other “rules” for dating attire. Also, feel free to ask him if it matters how you dress. If it does, he’ll tell you.
Be Yourself
You may be selling yourself, but you’re not a used car salesman. Don’t dress in any manner that you would consider inappropriate or weird. If you would have to cease being yourself to be his wife or girlfriend, then he’s probably not the guy for you.
The most important point here is that you have to dress for the body you have. Your goal is to accentuate your natural beauty, not create false beauty. Chances are, that’s well within your abilities. If that’s not good enough for him it could be the kick in the pants you need to lose some weight, but most likely he’s just a jerk that’s really just looking for a living sex toy.
Try For Sexy, Not Slutty
Sex is an inherent part of dating. No matter what he says or how wonderful a guy he is, staying with him means spending quite a bit of time in bed with him. On the other hand, any real man wants a woman who brings more to the table than just sensuality. You’ll need to walk the fine line between sexy and slutty. Showing some cleavage and leg is a good idea but don’t take either too far.
There are easy rules of thumb to know if you’re dressed too slutty or sexy enough. You look sexy if he’d accept an invitation to your bed, if looks are all he’s considering. You look slutty if you wouldn’t want your father to see you.
Go Easy on the Makeup
One of the quickest ways to go from sexy to slutty is to overdo your makeup. The point of makeup is, once again, to accentuate your natural beauty. You want to draw his attention to your face’s best features and away from your flaws, assuming you have any. If you did your makeup perfectly, he won’t be sure you aren’t so naturally beautiful that you don’t have need of makeup.
Wear a Skirt
Here’s where we get into the practical advice. Any man worth having, is looking for femininity, and there’s nothing more feminine than the skirt. Even so, it’s fine to wear pants if the activity calls for it or you’d never wear a skirt otherwise, given a reasonable option. It doesn’t matter what kind of skirt it is, or even whether it’s part of a dress or just a skirt worn with a nice top. Personally, I think a nice dress is the best way to go.
Dress Nice
People tend to pay particularly close attention to how they dress for job interviews, and when you think about it dating is essentially the same situation. The only differences are that it’s the most important job of your life, and there’s no chance for retirement, resignation, or dismissal. You’re trying to convince him that you should be his wife and the mother of his children, you should dress appropriately, considering something so important is at stake.
This is the time to break out one of your nicest dresses. Go ahead and wear those earrings you never get to. You’ve found yourself in the only situation where your looks should be of crucial importance.
Do You Need a Purse?
When you’re on a date, you may not need a purse. As long as he’s taking you out, you won’t need to bring any money or your debit card. You shouldn’t be using your phone on a date. I don’t know what you carry in your purse, but there’s a good chance you won’t need any of it, so a purse is just something to carry around.
Some Suggested Outfits
I can’t tell you exactly how you should dress, but these are some excellent options for a nice but modest dinner, or other classy date.
In Warm Weather
Wear a light sleeveless dress, something with a more flowing skirt. Pair that with some high heel or wedge sandals and a sun hat.
In Cool Weather
When the weather gets a little bit colder, you’ll want to switch to a heavy fabric for your dress, and maybe add sleeves. You’ll also want to add a light jacket. It’s also a good time to break out those tall black boots every woman seems to have, especially if they have a bit of a heel.
In Cold Weather
When it gets cold out, you definitely want to wear tights or stockings. Closed toe shoes are also a good idea, especially if there’s snow on the ground. Choose a heavier coat and a dress that won’t be crushed by it. As tempting as it may be, don’t wear any sort of hat that’ll mess up your hair. Keeping warm shouldn’t be a problem. If he’s worth having, he’ll try to keep things indoors when anything more than tights and sleeves are needed to be comfortable outdoors.
Reviving Manliness 