I actually have some “free” t shirts that are from local bands, from visual arts events, or of difficult-to-find films and the like, and every time I wear them I get numerous looks of interest or the comments other people will make to me about them spark a conversation…

Mind you, these are basically “work shirts” — I would never date in one — and yet simply BECAUSE they are original, have interesting ideas on them, and do not “sport” a recognizable product or logo of any kind I feel perfectly comfortable wearing them while working, working out, lounging around, or even running errands.

I’d like to mirror Dan’s comment above as well: If I’m out just running errands or getting a cup of coffee and happen to meet someone interesting, and then end up having a lovely conversation with her — would that person really be willing to judge me because I’m not wearing a polo or button-up during such a casual conversation and in such a chance setting?

Granted first impressions are important, since you never get a second chance to make a first impression…

But I should consider: Should I really want to go out with someone so pretentious that they would never consider wearing a “free” shirt in public (much less speak to a man wearing one), or is this setting an impossibly high standard for dating and interactions with women in general?

My basic rules for this type of casual wear is: 1. Must be visually unique and interesting, 2. Must be thematically interesting or intriguing, 3. Must be topical to something I would be happy to talk about if anyone asks, and 4. SPORTS NO LOGOS OR ADVERTISING.

thoughts? Feelings?

In the past I’ve known women who loved them, and women who were indifferent. Now I know one who would considers them as appropriate as the free t-shirts discussed here.

Does it depend on the woman? Is it a style that came and went? I’ve always considered them a “casual fun shirt”. -Regardless it looks like they’ll be staying in the draw for now…

As many mentioned before, I do not wear T shirts when I go out except at home, at the gym or biking or taking a walk around the neighborhood. Do I need to go and look myself in the mirror and make sure the darn thing fits me well????I live in the Midwest near Detroit and we just don’t do that around here. I do not want it to fit well because I am going to do something physical and I want it to be loose damn it!

I must confess I have only Free T shirts, I just can not pass them up at conferences…I end up giving most of them away to nieces and nephews overseas and they do make great gifts. And I wear them in occasions cited above…I have not bought a T shirt in many many years, why buy one when I get so many for free…If I invested all the money DW spends on his T shirts alone it would make me filthy rich very soon:-)

Going out on a date of course with such a Tshirt on is awful. But are you saying that if I am at the gym and have my free T shirt on (a nice 100% cotton one with some resemblance of…style) women will look down on me?…If they are so conscious and pretentious why should I bother be interested to them? They are probably Paris Hilton wanna bees anyway, I bet you they buy People and Star as they wait in line in the grocery store.

And I also agree they make great tools to clean houses and cars too!

I am contemplating buying my first T shirt..this one:

http://www.wackyplanet.com/need-more-cowbell.html

as an SNL fan, when I saw it it just brought tears to my eyes remembering Will Ferell banging it!

I agree with you. My brother is King of the vintage shirts and some of the old company shirts are great as long as they fit.

Plus most none of those starchy things that fit like a dress would ever make vintage!!

The only thing they make is a good rag!

But i have a friend who goes to the salvation army and scours the place for old company picnic shirts, town fair… anything vintage looking.

and he gets complimented by girls on his style constantly.

I do realize you’re talking about the starchy oversized ones.. but i wanted to clarify for those who want to wear vintage.

Wearing a google shirt now might be lame… But wearing an IBM vintage t-shirt from the 80s might be cool

It’s about time you made a Free “David Wygant” T Shirt!

I will rock that thing all day every day!

Make sure you make small sizes for Kubie and I.

Thank you

Vince