Does Your Man Dress Well?

A well-dressed man is every woman’s dream.

Is your boo a little lacking on the style side? Here are some reasons why he might be missing the mark – plus some ways to turn that drab into fab!

Hands up if your man dresses well (we’ll wait). A well-dressed man seems to be a bit of a rarity these days even though there are so many great trends for men. Being a well-dressed man can do so many things for your life and while many women make an effort (thanks babes, you all look amazing!), their man ends up looking like a bit of a slob because he isn’t putting any effort into his style.

As a man (and your new men’s fashion guru), I’m going to let you in on a few secrets about why your guy may not always be down to dress well. Having styled and worked with many men over the years, here are the four main reasons they’ve told me as to why they lack style and don’t spend a lot of time or money on their appearance.

He’s afraid to dress well

For a lot of men it is the fear of being ostracized especially by other men for taking an interest in clothing and appearance, that he simply doesn’t bother and avoids it altogether.

Some messages that are shared through our culture show that a man who spends time on his appearance is somehow emasculated; his sexuality is in question and he might even be interested in arts and culture, rather than rugby and drinking. Not a real man!

These stereotypes are wrong because it’s not like that at all, in fact it’s extremely manly to dress well and oozes self confidence. I have never had so much attention from women since I dressed well and if that isn’t masculine then I don’t know what is!

Men need to understand that dressing well is just grooming and that grooming is an essential part of a happy healthy masculine life. Do you think an unkept ungroomed animal is happy or healthy? No!

Male and female animals of other species both groom exactly the same. The males are equally as groomed as the females. Grooming isn’t male or female, it’s just a part of everyday life.

Men don’t need to dress up in a suit to adhere to these principles, they simply need to have some intention about what they’re wearing, how it fits and how it looks. To them it may seem ‘too much’ but it is simply just putting in effort.

My suggestion to help him change: 

Talk to him about it, ask him if he thinks that way? Explain to him that you think a well dressed man is manly, masculine, confident and very attractive (if that’s what you think!) He probably just needs some reassurance from you which can go a long way and set him on the right path.

As far as derogatory comments from other men about his appearance, you’ll usually find they will come from men that dress like a boy. Other well dressed men will usually compliment. If the negative comments are coming from his friends, then maybe he needs to think about who he surrounds himself with.

He’s feeling down about himself

We all have our ups and downs in life and that’s pretty normal. When someone is feeling down about themselves they tend to let themselves go. Dressing poorly, letting your physique go and paying no attention to personal grooming are common signs. If your man is like this, then a new masculine wardrobe is one way to get him out of the doldrums, make him feel better and boost his mood. The problem is getting him motivated enough to make a change.

My suggestion for change: 

I would simply discuss this concept with him and see if he agrees. If he agrees and it’s logical to him he should respond in a positive way. If he’s up for it then make a plan of change.

Start with a wardrobe audit, followed by some clothes shopping. Additionally creating a new grooming routine, scheduling regular haircuts and possibly a new exercise program will be a great way to approach it from many angles. Self care should hopefully kick in and he should feel a lot better immediately.


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He has never been taught to dress well 

Did his parents teach him? Do his parents dress well? Did he grow up somewhere where dressing well wasn’t the norm? If his parents (especially his father) didn’t dress well then it makes sense that he may not also. It’s not always the case but it is very common.

Dressing well isn’t taught in schools and boys generally don’t read fashion and style magazines when growing up so they tend not to know a lot about clothing and style. Most men just simply missed these valuable lessons.

My suggestion for change:

He needs style education! There are some amazing free resources available for men now on the internet, so here are some places to start:

Youtube – My  stylist recommendations include: Alpha M, Gents Lounge, Real Men Real Style, The Modest Man, Tanner Guzy and He Spoke Style. Send him video links and/or watch videos together. I would suggest you critique these channels before recommending any of them as their styles are all a little different.

Men’s style websites –,,

Pinterest – create boards of men’s styles that you think look good and show him. If he knows what you like, then he might start moving in that direction.

He doesn’t think it’s important to dress well and doesn’t see the value

If you’ve never really dressed well you’ll have never experienced the benefits. You’ll also have little idea about what a difference it will make to every part of your life.

Dressing well is so important. He might be unaware that we are all sometimes judged by our appearance. I know you shouldn’t judge a book by it’s cover but in our fast paced society a book’s cover can be just as important as it’s content. So if he wants to get a leg up in life and be more successful then he needs to start paying attention to his appearance.

The main benefits include getting treated with more respect, giving off a stronger first impression, people will listen to him more, boosting his confidence, increasing his perceived status and people thinking he is smart and more enjoyable to be around. It’s a no brainer really!

My suggestion for change: 

Give him a challenge with a reward at the end. Suggest he dresses well for one calendar month so he can experience the benefits.

You’ll probably need to help him plan his work and social outfits for 30 days so it doesn’t fall to pieces, and is still cohesive after a couple of days.

At the end of the month discuss his observations and experiences of what he noticed. I guarantee he’ll see the benefits. Once he is convinced hopefully you’ll have a man who wants to learn more about how to dress well and he’ll be hooked.

I hope this helped and you get a better understanding of your man’s mind when it comes to dressing. Of course there can be many other reasons why he doesn’t dress well but these are the most common four I have come into contact with.

Are you going to help your man get his fashion groove on?

simon scottWritten by Simon Scott

Insta: simonscottstyling              Email:

Simon is a menswear stylist with a love of travel, working out and getting dressed up! He has a passion for helping men dress better and there is nothing he loves more than seeing a well dressed couple out together.


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