What apparel looks bad on men under 40?

We've all seen the thread about men over 50 and what they should not wear. Now, how about a thread for the men under 40? What apparel items make them look very out of place? Please refrain from the obvious stuff like canes with bicycle horns etc. I'm talking about male fashion mistakes there the person thinks they look cool, suave, sophisticated (you get the idea) but really all they make you want to do is slap them into next week. Yes, there is an element of YMMV, but we won't worry about the outliars.

I'll start. I think a fedora looks generally TERRIBLE on men under 40. Same with a pork pie.

Parachute pants.

Depends upon the clothes and the man.

Suspenders. Novelty tees. Diving or other specialty watches worn to work or out to dinner. Athletic or other specialty footwear worn to work or out to dinner. Loud ties. Too much cologne (it is, after all, something you wear) or any amount of cheap cologne. Being the first guy on the block to wear a new fashion trend. If in doubt about what to wear, go conservative. Unshined shoes.

There are some looks that I cannot pull off. I look good in a suit and tie, terrible at wife-beaters. Hats make me look like a dimwit.

I don't think it's a matter of age but rather that of body shape.

Camo clothing outside the duck blind.

I didn't think I could pull off a fedora until I hit 40; perhaps I could have, but . . . .

I can think of nothing that would look good on a 29 year old that would instantly look bad at age 40. Did the 40 year old gain 40 pounds? That would influence some decisions - but it might for the 29 year old as well. Skinny jeans? I don't like them on the 29 year old, so who knows?

I'm tempted to say that by the time you reach 40 you should have learned to take your hat off inside, unless you're going in the next inning - but that's a different thred.

Make your sartorial decisions based on what looks good. Purchase clothes that fit (or take them to a tailor). I admit I often ask my wife if she thinks the person walking by has any mirrors in their house. So if you can't tell by looking in the mirror ask your wife, or a friend. It's like music: "If it sounds good it is good."

lmarkow said:

I didn't think I could pull off a fedora until I hit 40; perhaps I could have, but . . . .

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I havent seen too many any young man pull off a broad brimmed hat in “real life”. Plenty of times I have seen it in magazines, TV, etc., but every case where I have seen a young man wearing of a fedora / pork pie / homburg / etc. - it is an affectation.


Which is surprising, because I have seen young guys wear a panama or cowboy hat in public and it looks completely natural.

So many of these issues are cultural, or situational, or subject to rapidly shifting fashion trends, it would be difficult to pin anything down. For example, I like berets, but SO many people don't. "What are you wearing that for? Are you a thirteen year old girl today? Is this one of your weird thought experiments?" But if you were vacationing in the north of Spain, Argentina, or Uruguay and you meet me there wearing a beret, it wouldn't be a problem.
When I first got back to California and decided to finally use my GI Bill at the local community college, I met a rockabilly kid in one of my first classes. It was still very much a subculture then, an I was living kind of out of the way in the High Desert so I hadn't seen it yet. I though "What's going on with this guy? He's got balls dressing like that." Then he found out that I liked to play pool and invited me to a pool tournament at a local pool hall (he shouldn't have done that...), and when I showed up the place was packed with rockabilly folks, and suddenly it wasn't all that weird.
This kind of reminds me of that other "What shouldn't over 30 year olds wear" or whatever it was. Just let people do what they want, I could care less, as long as it's not harming me or mine.

Most subcultures have norms of dress / appearance that make our little "dos and don'ts" lists look like a slip from a fortune cookie. If one chooses to adopt that style and/or lifestyle - have at it.

Those that skew more toward the mainstream may benefit from the suggestions outlined, as being aware of a "rule or norm" is one step - it is up to the individual to decide whether to adopt or ignore it

I agree that it's not so much about age as it is about the person. That is to say - the whole package matters.

If someone has picked the wrong clothing for their body type, or if they have one piece of clothing which is conspicuously different from the rest (i.e. fedora + sneakers), or if they're not confident in their clothes, they will almost certainly look bad no matter their age.

Consider the last movie or television show you saw which was set in the past -- you probably saw men of all ages wearing fedoras, doublets, loincloths, tricorns, hose, kilts, robes, ... etc. And (unless it was a bad movie) they probably all looked just fine -- because someone in the wardrobe department took the time to dress them properly in a complete outfit which not only fit, but actually suited them.

Santa Clause suit. That's for old fat guys.

Dang, I'm over 40 but under 50.
Does that mean EVERYTHING looks good on me, or that nothing does?

TinyTim said:

Suspenders. Novelty tees. Diving or other specialty watches worn to work or out to dinner. Athletic or other specialty footwear worn to work or out to dinner. Loud ties. Too much cologne (it is, after all, something you wear) or any amount of cheap cologne. Being the first guy on the block to wear a new fashion trend. If in doubt about what to wear, go conservative. Unshined shoes.

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I've worn suspenders since I was in high school and still do. Not every day, and usually with flannel or wool shirts, jeans or wool pants, and work or pac boots. I'm assuming you aren't referring to people who live in the country and do things like cut firewood, hunt, or just spend time outdoors in general?

JaredB said:

I've worn suspenders since I was in high school and still do. Not every day, and usually with flannel or wool shirts, jeans or wool pants, and work or pac boots. I'm assuming you aren't referring to people who live in the country and do things like cut firewood, hunt, or just spend time outdoors in general?

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It's kinda funny how guys always come in here and are like "Well I'm a rough and tough dude who wears X because I do X". Well yes, your work clothing is what you wear for utilitarian reasons. It is not your best looking clothing. The fact that you wear certain clothing while working or hunting doesn't mean it actually looks good on you outside the context of that particular task. See: Bunch of young dudes at a country bar with floppy RealTree jackets on a Saturday night.

MontyBurns said:

There are some looks that I cannot pull off. I look good in a suit and tie, terrible at wife-beaters. Hats make me look like a dimwit.

I don't think it's a matter of age but rather that of body shape.

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+ 1 to this. I am a larger man, and I have to be very careful about my choice of attire. If I am dressed for work, the cut of my pants is very important, since a tucked shirt will not hide my front bulge.

As far as hats, I can get away with a few styles. Ball caps are great for casual wear, if we are outside, and I have been able to pull off wearing a bowler hat when I am on stage. With hats, I believe the rule of thumb is that the brim must be larger relative to the width of your shoulders. Narrow shoulders = short brim, wide shoulders = wider brim.

wildwest74 said:

+ 1 to this. I am a larger man, and I have to be very careful about my choice of attire. If I am dressed for work, the cut of my pants is very important, since a tucked shirt will not hide my front bulge.

As far as hats, I can get away with a few styles. Ball caps are great for casual wear, if we are outside, and I have been able to pull off wearing a bowler hat when I am on stage. With hats, I believe the rule of thumb is that the brim must be larger relative to the width of your shoulders. Narrow shoulders = short brim, wide shoulders = wider brim.

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In your role of performer, you have Carte Blanche to thumb your nose at any and all sartorial guidelines. The suggestions most folks are putting out there relate to casual social situations. Wearing suspenders or having cargo pockets as part of your work attire is great if it makes your working conditions better - just like wearing a piece of vintage apparel or a period piece (like a bowler) adds a level of distinction to a person on stage.

Skinny jeans, spandex biker shorts/pants, long denim skirt, and crushed velvet anything including capes. Though I find it entertaining to see those who do try and poll it off and glad that they're at least wearing cloths. In the defense of th guy in the denim skirt, I believe he is homeless so he's most likely happy to have something warm to wear and shouldn't knock him for it. But as long as these guys are happy and not bothering anyone, I say let them carry on and wear what they want.

DCRIII said:

....and crushed velvet anything including capes.

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I dare you to say you can't pull off the cape look. If its good enough for Frank Costanza's lawyer, its good enough for anyone: