Dating Over 40; Dressing the Part, Acting your Age

Oh so often women wonder why men aren’t attracted to us, or why they get so turned off after a first date, but  have you looked at everything leading up to this first date to see what it was that went so terribly wrong? Could you have fixed it? Planning and preparation for this date means details girls and you need to look great because we have a lot of competition out there that can sweep a man away if we are too busy with our head stuck in the sand. Don’t muck it up.

So where do you start once he asks you out? In all honesty dressing for a date says a lot about what you think about yourself and about your guy. The outfit that you wear out should be one that makes his eyeballs fall out with lust and admiration. It’s not that you have to be phony or dress differently, but you do have to dress appropriately for the plans he’s made for the date. Most men that I know like sexy and simple. The little black dress is the only way to go in my opinion, nonetheless, there are a variety of things that you can wear to turn his head in a good way. My suggestions are quite simple actually, so please, pay attention to what he has in store for you, and if he doesn’t tell you ask how to prepare/dress.


In my opinion, it would be a really smart idea to ask the guy what kind of evening he has planned? If he wants to keep it a surprise, then ask whether you need to dress as you would for the office, for a sports event or for an elegant party. That gives you a range in which to choose your outfit. So many women that I know at my age are in their later 40s and want to dress like someone half their age. Not only is this a bad idea but it make you look so tacky and cheap. You didn’t get through your entire life riding on the tails of someone your daughter’s age or a woman in her 20’s or early 30s so for God sakes, dress the part, it shows your maturity and it labels you as someone with class…and truth be told men love classy women with taste.


How you dress says so much about who you are. This means get rid of the cheap crappy looking stuff in your closet and ask your friends for some help and reinforcement! If you have younger friends, don’t bother asking, they’re only going to give you suggestions of how they would dress and trust me, most if the time, you wouldn’t want to be caught dead walking out the front door.  If you go out in a halter with cleavage barely contained and a mini-skirt that slightly larger than his handkerchief, then you’re sending a message that he reads as “YES” and other women quickly label “slut.” Oh you’ll get plenty of attention, but the wrong kind of attention! Is that what you want?


Listen, there are stores to go to for really nice apparel at reduced costs… so when you go to a store, DO NOT go straight to the ‘juniors section!” You aren’t a junior and you’ll only make a complete fool out of yourself. Girlfriend you want to hold your head up and look good for this person. They deserve it and you need to represent not only who you are but you’re representing all the other middle-aged women out there.  Junior are meant for juniors, plain and simple…so stay out of that department all together! You may think you look good, but it’s embarrassing to say the least. 


Dressing for a date when you aren’t sure about the plans is like going to a job interview. If you don’t know what they interview is for and what position of the company, my suggestion is this; dress for the job you want, not for the job you have. There is a lot of competition so get it right. You only have this one chance, this one opportunity to show him that you are a woman with a good head on her shoulders. It’s better to dress up than to look under dressed. That means take the extra step, make some effort, and dress up just a bit more. 


For a date, apply that advice. If you aren’t sure what to wear, go with business casual and sensible shoes. Less is more. This means you don’t need to be all blingy and don’t wear a ton of make up. Men love simple and natural. If you are wearing so much make up that it takes layers to remove it, stop right here! If you wear a sleeveless top, bring along a light sweater, or a shawl since you don’t know whether you’ll be inside a chilly movie theatre or sitting outside at a patio restaurant after the evening temperatures drop. 


If you’re getting back into the dating scene after a few years, take time to look over the current magazines for casual styles. Go simple with colors too. Red, Black and White are the most popular and eye-catching colors. Then ask other women who have similar styles to yours what they would wear for a date. Ask for advice! People are more than willing to give it and you need it!


Basic rule of thumb: if you haven’t dated for five years or more, don’t wear what you use to wear on dates. Chances are with your dating scene absence with a wardrobe that needs to freshen up.So pull out that credit card or unfreeze your assets and splurge this one time! You don’t have to buy all new clothes – just edit your outfits and add a bold item that’s current.  Even if you’ve lost lots of weight and just got a face lift, don’t go shopping in the junior department after age 25! That is a serious NO and a huge turn off. Most men our age probably have daughters in their 20s and God only knows that he isn’t taking his daughter out so don’t embarrass yourself dressing like her! 


You’ll add to your age by trying to look too young, and you’ll be the laughing stalk. Act your age and damn it be proud of it! If you want to keep it very simple, you can never go wrong with a little black dress. I have two from Michael Kors that are simple and stunning. They don’t say ‘look at me, look at me’ …they say sophistication at it’s finest. After all, it’s about being comfortable and confident with who you are as a woman, yet realizing that a certain amount of effort is necessary to look tres jolie, very pretty. This look requires some basic classic pieces that never fade from fashion, creativity, and a sense of self-expression. This look is about communication. The eyes, the lips, the hair, are all ways in which a woman communicates. Fashion with style is not only about function and looking well, but is another way in which we communicate our inner self to the outer world.


Dressing  sleazy or provocative is out, unless you want to be labeled as trash. Trust me, simple is better and you can never lose in a LBD. Start the evening feeling good in an outfit that makes you feel special even before he walks through the door! Remember, you want to really stand out and if you have the right dress or outfit on, you will be a vision in his mind that stands out for a very long time. That memory of you will be embedded in his brain, so look good, smile and just be you…and you’ll have him coming back for more.


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