I'll admit, while I am old fashioned at heart (nothing looks better on a man than a suit and fedora), I've worn trendy jeans/shorts/sneakers/t-shirts my whole life. Unfortunately, my reasons for doing so are terrible.....not only is this fashion in style, but women my age seem to find it attractive, and the clothing is just convenient/comfortable to wear. I am sick of following the fashion trends of my generation though, and I want a more conservative, old fashioned yet mature look now that I am approaching my mid twenties.

Can anyone give me some pointers, or perhaps point me in the direction of a few links/articles that would show me classy and timeless casual wear for men?

Also I have one more question....to men who wear Fedoras:  Do you oftentimes get stares? I would LOVE to own one and wear with a suit, but since I look young enough as it is, I'm not quite sure how well I could pull off the look. I only wish I had the courage and confidence to truly sport one like you do! I'm not quite there yet, but I am working on being myself despite what others may think. It's harder than I thought.

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I wear the fedora ONLY when the occasion calls for it. It definitely is not a casual hat. But when I've gone out with the buds a few times I've gotten some stares and on a dare I wore it out to a night club .... didn't seem to pick up the ladies. Not with all the (forgive the term but when I say it you know the style) wiggers. Wearing their 59-50 hats and design tee's. A man in slacks with a fedora looks like an anachronism but it is what it is.

tldr: Don't wear it to casual events. I wear a nice flat cap though for casual occasions.
Man, as long as your clothes are clean and well kept, it doesn't matter how you dress. Wear your clothes with confidence and you will look good in anything.

I, personally, only wear t-shirts around home. If I leave the house I am wearing a button down shirt. People have commented about the fact and I just reply "to each his own".
Can anyone give me some pointers, or perhaps point me in the direction of a few links/articles that would show me classy and timeless casual wear for men?

OCBDs.
Polos
Khakis
Dark, slim jeans
Tropical Wool trou
Linen trou
Boat Shoes
Chukka boots
+1. That advice works well for me.
I'm no fashion guru, but I know that a 20-something wearing a fedora will look rediculous. Unless you are a famous R&B performer, any fancy hat will just look rediculous...and even they look rediculous. Being old-fashioned is great, but dressing like it's 1950 is kind of weird. Boat shoes???? Those went out in the 80's.

It's not about having the courage to rock a fedora or sport some boat shoes...it's about not looking tradgically stuck in a time long ago. I mean, why not double up the polos and flip the colars up? How about a nice powdered wig and bloomers? Perhaps if you are a professional who wears a tailored suit to work and carries a briefcase you could possibly get away with the fedora...but it would still look a bit out of place. Like I said in another post about clothing, you don't want to come off as a "dandy".
The ONLY person I know who still wears boat shoes (and I grew up wearing them in the 70's and 80's) is my 67 year old dad. The last thing boat shoes are is trendy.
This is quite incorrect.

See, e.g.:

What's your point? Just because they come in colors doesn't make them trendy. They are still goofy old-man shoes. I swear to you I have not seen a man under the age of 50 wearing boat shoes. Seriously, I lived in these things as a kid, but haven't worn them since the early 80's.

I do own a pair of solid color grey Vans. Those are still very popular in California. Very retro.
The point is 21 different pairs of boat shoes, ALONE, are available at the hipster mecca of trendiness - Urban Outfitters.
Who is wearing them???? I don't care what company sells them.
Perhaps it's not the case in California, but they're ubiquitous on the east coast.

They used to be exclusive to WASPs and their progeny - but are now on the feet of every second hipster around here.
I've lived in Florida, Virginia, Texas, Georgia, Maryland, South Carolina, North Carolina and a few other states around the nation...I haven't seen a pair of boat shoes on anyone under the age of 50 since the 80's. They used to be huge back in the day.

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