Confident Man in black shirt

Confused Male Fashion

There are lots of men that are confused with fashion styles and I was reading the following conversation on the Male Fashion Advice subsection on Reddit, and I found it very interesting to share with our readers. I have modified it slightly to remove some of the swearing.

The Question: I see a lot of fashion styles and there is no way in hell I could pull off

“I’m almost 30 now, whilst looking at male fashion blogs I see a lot of fashion styles where there is no way in hell I could pull them off, or get away with them. I have been wearing jeans (not tight jeans, normal jeans) and a t-shirt or polo neck my whole life. Sometimes my friends have made fun of me for it but they ALWAYS end up wearing that as their standard garb a few years down the line, when kids start appearing and the ring is on their ladies finger.

Now the suit stuff I can understand. During your work hours, the suit is the most important set of clothing you own, it need to be spot on all the time. But outside of work? I pretty much just wear what I stated above, in whatever combo happens to be clean and I know most of my male friends are the same.

But some of my friends do dress up and work out. Which brings me onto the attitudes of male fashion; there seems to be a very definite split in opinion on whether men should even bother dressing up. With many men AND women referring to well dressed, preened and built men as “posers” and “douche bags” (Or of course, the old “oh he must be gay) which seems odd as this does not really ever seem to be directed to well dressed women.

Women laughing at men’s dress sense

You see it all the time, some girls sitting on a bench with their Starbucks when a well dressed guy walks past in the summer sun looking great and they just burst out laughing, while a different group of girls nearby just stare and drool.

I don’t get it at all, looking good is subjective sure, but such a clean split in attitudes? I would rather stick to my t-shirt/polo neck and jeans combo and just blend in as I have always done rather then spend money dressing in a way that would make me feel conspicuous. I was just wondering what other peoples experiences with this was, have you come up against negative attitudes towards male fashion for no good reason at all?

And also do you see male fashion as very much of a “young persons thing IE: <35ish”. I’m keen to hear what people on here think of this.



There is always going to be someone who thinks you look awesome, and someone who thinks you look silly. Dress in whatever makes you feel good and confident. In a recent survey about self-esteem, almost all of the 2,000 men questioned, admitted that they struggle to feel confident. I find that when I style men a key factor in boosting their confidence is guiding them to make a conscious effort to dress well.


Answer 1

A well dressed guy walks past in the summer sun looking great and they just burst out laughing? I have never seen or heard of this in my entire life. (I am an avid participant of the ‘stare and drool’ category.)

The problem is, most guys do dress in a t-shirt and jeans. And while there isn’t anything wrong with this, there is a certain level of “acquired taste” and learning curve that comes with men’s fashion. A lot of guys think desert boots are butt ugly when they first see them, and most will be converted. A lot of guys think slimmer jeans are ridiculously tight when they first see them, until they realize how good their bums look in them! etc etc.. Over time, they come to appreciate the aesthetics of new styles and then want to emulate them. We call this growth.

The “gay” connotation is a different animal, and a pathetic one at that. It’s a weak defense for sloppy, shlubby guys to defend their self-esteem and attempt to up their ego. It is not “gay” to care about your appearance, unless gay = larger levels of self-esteem, self-respect and consciousness of others (and it is certainly not even remotely bad to be gay to begin with!).

I’m planning a NYC trip and I feel my aesthetic has become too ridiculous and constrained, so I’m going to buy myself some really “weird” outfits which will not be socially acceptable for me to wear at school. Oh well.

Men Dressed in Red with red hat

Answer 2

I’ve never run into this attitude. Usually when a man is well dressed it’s a positive, for the people I know. Maybe you’re confusing dressing up with dressing well? I have seen dressed up douchebags in their Ed Hardy shirts and overly distressed True Religion jeans. It rocks.

Man dressed in Tartan trousers

Answer 3

I see these types of discussions pop up pretty often. It’s something a lot of people don’t grasp or understand for whatever reason. You might agree with me or think I’m an idiot, but here’s my take:

Everyone has their own reasons of dressing well (or dressing in their own specific style/sense). The main reason for me wearing the clothes I choose, is to make myself feel happy, confident and good about myself. I understand that people are going to come to their own conclusions about me without even knowing my name, that’s life. I have never once had a concern of someone thinking that I am gay simply for caring about how I look. If a guy thinks I’m gay, it doesn’t matter. And personally I’ve never had a girl thinking that I was gay, prevent any romantic moments. If you’re worried about being called gay you might be a little insecure or homophobic anyway.

When it comes to guys not caring about how they dress, that’s their decision. No one thinks that you have to care, or even cares whether you care, unless they’re invested in your life somehow. Guys who dress awfully often look like they lack confidence or care for themselves and that’s certainly a put-off for any woman.

You say that you’d rather just dress to blend in. This makes you sound like you lack a lot of confidence and standing out would be a bad thing! Why would you want to blend in with a bunch of boring people when you could stand out from the pack. You don’t say anything about a wife, so as a (possibly) single guy why wouldn’t you want to stand out to the opposite sex?

I like to dress nice sometimes just to make people think to themselves, “why is he so dressed up?”, or “he must have some place to be”. I feel that when people have questions to ask about you, it makes you so much more interesting and desirable. Keep them wondering.

Quit worrying if people think you’re gay. Dress to make yourself happy and confident. And please, ditch trying to blend in, stick out like a big sore thumb and be happy!

Songzio Asian models - Tanihara Shosuke

Answer 4

Just ask yourself “What Would Kanye West Do?” The answer is universally correct (it doesn’t matter if you like him or not). Dress how you wanna dress and sod the haters. The same people who turn up their noses at well dressed people would maybe drool over some punk or goth’ed out guy, and the people who are impressed by good fashion would probably laugh at a punk rock type guy.

Stop dressing for other people, and start dressing for yourself! Your confidence and happiness matters and as long as you have these two things, you shouldn’t let other peoples opinions, tarnish your ability to dress, to suit yourself.

James Long Men Fall Winter - 2012/13