Ditch The “Old Man” Clothes If You Want To Attract Women

If you don’t care about how you look then don’t waste your time and skip this article.

How You Dress Can Make You Look 10 Years Younger

I’m going to cut to the chase and not sugar coat it which is how I am 100% anyways. How you dress can have a dramatic impact on how you feel about yourself and how others view you. Many of the men I’ve worked with at the beginning didn’t even think about clothes and how they looked until I brought it up like I’m doing right now.
Whether you are dressed for business or personal, you’ll want to see if your current clothes accentuate your physique (body) or do they make you look even older. Too many times I see men over 50 wearing very baggy shirts and pants that are way to big around the thighs and arms. What this does, is make a man’s body look sloppy and will not portray you in your best light at work or in social settings.

Burn Your Tommy Bahamas

50 is the new 40 in my opinion and if you are a man wearing Tommy Bahama clothes it is screaming “I’m an older man”. I get it. They are extremely comfortable, but they are oversized for starters and the bowling shirt look is just not happening in 2020 i if you’re a man who wants to be attractive to the opposite sex. If you’re married your wife most likely loves you wearing it. Why? In my opinion, married women don’t want their husbands looking good. Now before you ladies out there read that, I want to share a statistic with you.

Ignore What Women Tell You

Having been divorced myself for over 2 years, I hit the dating world (online) hard. I wanted to know what made women tick. What their motivations were, and what they wanted out of a man. Do you want to know what most of them (not all) told me when I asked the type of man they are attracted to? I was flabbergasted hearing it. The majority of them said they always want to be slightly better looking and in better shape.
Why do you think that is?
This type of woman doesn’t want to be challenged in anyway. They want to be comfortable that their man is not going anywhere (straying). Many of these of women are insecure. They don’t want a woman to be attracted to their man as they would feel threatened. A secure woman on the other hand would want her man being the best version of himself. Looking great and with tons of confidence. Think about that for a minute. And no, this is not all women, but I’m comfortable saying
a lot of them.
I want you to be the best version of yourself…for YOU!
When it comes to what you want out of your life, you and only you make the decisions for yourself. You don’t need a woman making them for you. You’re a man for crying out loud. Be a man! Step up and own where you are at in life, and if it’s not where you want to be do something about it…NOW! I digress. More on that topic in another article so stay tuned.


If you want to be perceived as an alpha male which is what women are attracted to, do not ever wear pastel colors. This comes across feminine and not attractive to women. Instead stick to grays and blacks, with the occasional blue or light brown. Grays and blacks give off a more mysterious vibe and can also be slimming for men that are carrying extra weight.


Let’s start with your pants. Whether you are wearing slacks for work, or jeans for social, you need to get them to fit right to accentuate your body. If you are currently carrying extra weight, you don’t want to compensate by getting baggy pants that are loose on your thighs. Instead, you want to have all your pants just slightly loose, but more fitted looking. This will give your shoulders a broader look, and can minimize the weight you may be carrying in your belly.
Warning: Ditch the cargo pants. Do not EVER wear them again! Nothing screams “I’m an out-of-touch dad” louder than these hideous pants.
Test: Put on your favorite pants, if you can grab more than a fingertip of material around the thigh area they are too baggy. Either get rid of them, or do what I do and get all your pants altered. It may seem like a pain, but trust me…you will be happy with the outcome.
It’s not just the thighs, it’s the lower leg as well. Make sure the width of the lower leg and hem around your shoes is not too wide. It should not be more than 7.5 to 8 inches at the most. Any wider and it screams “old man”.


Warning: Unless you are at work, do not EVER tuck any of your shirts in. That’s so 80’s and not going to help you look your best. Tucked in shirts accentuate a belly for starters and do not present your body in the best light.
Now regarding fit. If you are wearing a button shirt with long sleeves, take a look at the fit. Look at your arms and body.
Test: Take your fingers and pinch the shirt around your upper arm and pull it away. if you have more than an inch, it’s too baggy and will make you look sloppy. Either dump the shirt or get them altered to have about an inch around the bicep and even forearm.
Tip: For social settings a simple t-shirt is all you need. But…how that t-shirt fits is critical. I wear t-shirts 90% of the time and get compliments quite often.
When you buy t-shirts again make sure they are not oversized. This is not flattering even though you may feel it covers up your belly. This is where you need to have a heart-to-heart with yourself if you truly want to be the best version of yourself. Don’t hide underneath loose, baggy clothes. Get comfortable being a little uncomfortable even if you are overweight. Force yourself to wear more fitted clothes. It will motivate you to loose some weight. There is a mindset underneath how men dress. I want you to think differently from now on.


Shoes are a personal preference. You and I, I’m sure are way different in the styles of shoes we like to wear.
If you’re dressed professional for work, I would recommend whatever you like. I’m more focusing on lifestyle with this site and my coaching. With that being said, depending on the outing, sneakers are a go-to 90% of the time. But when I say sneakers, I don’t mean ones that I call “old man” sneakers. There is a difference.
Mesh sneakers, or sporty sneakers look great with jeans and shorts. Even some models of Adidas are quite flattering.
Tip: Don’t go shiny! If at all possible, stick to blacks and grays. And get a more flat color that is not shiny.


I could write a ton more on men’s fashion over 50 but hopefully you found it helpful. It really will make a difference in your confidence and how you are viewed by women. If you did, please share this article and website with all your male friends.
Don’t forget to head over to our Facebook page and become part of the community: https://www.facebook.com/thetransitioningman and also on Instagram at https://www.instagram.com/fit_men_over_50

Next Step

If you want to be the best version of yourself and need guidance, contact us today. We offer fitness, lifestyle and dating coaching.