When it comes to clothing, men are very sensitive about comfort.
However, you may need to re-define what comfortable means if you want to look your best. I will never dispute the fact that looser fit, well worn, pajama feeling, clothing is the most comfortable to wear. However, I hope you will recognize, it's not your best look and definitely not appropriate in the workplace and perhaps even out in public.
Clothing that fits better, looks better. It's a mantra I repeat often because men commonly wear clothing that doesn't fit well; generally it's too big. However, they have been wearing clothing in this larger size and fit for so long, they don't know any different. When they first try on clothing that actually fits, they are often self conscious and unsure. Some even venture to say it's not "comfortable." However, when I ask if it hurts and where it's uncomfortable; the answer is usually they just aren't used to wearing clothing that fits.
Men, you aren't alone. Women have the same issue. Comfort is 50% physical and 50% mental. For example: I love wearing high heeled shoes. I am asked quite often by women (in flats) if my shoes are comfortable. I answer truthfully: "Yes, they are (I don't buy shoes that hurt because I know I won't wear them)." Would I run a mile in high heels or go hiking? No, don't be ridiculous! However, when I want to look my best and feel confident, I put on a pair of heels and I truly feel comfortable wearing them.
Do I recommend you buy and wear clothing that physically hurts even if it looks good? No. However, I do recommend you wear clothing that fits better. Re-train your mind and body to feel comfortable in something other than clothing that fits like your pajamas or athletic wear. For example, dress shirts that fit better are not going to allow you to wind up a fast ball. However, you shouldn't be wearing a dress shirt on the ball field anyway. A proper fit should allow you to move freely within reason. People who say "I can't do the splits in these or I can't circle my arms widely" need to give up on looking their best altogether and sign up at the nearest Gymnastics Center.
For men wanting to become more fashion forward, modern, up to date and looking their best, they may need to re-define what comfortable is. Trust me, you will look so much better and feel more confident about yourself when you wear clothing that fits well...you will feel UNcomfortable wearing your baggy clothing outside your house again!
-Lisa Bruckner, Hendricks Park

Great post.
Excellent picture of a comfortable slob. The real problem with dressing "comfortably" instead of appropriately is that the former is selfish, while the latter displays the true gentleman's consideration for others.
Even though my employer does not require it, I wear a jacket & tie to work every day--that is, on those days I don't wear a suit & tie. It shows a professional attitude to all those I work with, and I have noticed that I get treated differently--almost always better--when I am so dressed.
I wear a jacket & tie to church; this, too, shows respect for my fellow parishioners and to God. It accentuates the dignity of the occasion.
I never get "are you comfortable?" questions, but I do get "you look nice" complements. Besides, I honestly enjoy wearing a tie!
Posted by: Bill | 08/08/2009 at 11:02 PM