Whatever makes you happy. Everything I have is comfortable as well. Whether it's bought new or used or given to me by someone who's paring down, it's got to be comfortable or it doesn't belong in my closet.
I have never found anything new to be comfortable,
@AllThatJazzZ ... It's a love/hate thing for me buying new... New jeans are awful till half the blue is wore off em. New sh*tkickers are notoriously torturous, as any cowboy will testify, and any mountain boot takes years to break in. Same with coats, same with about everything... Perhaps it is a difference between female clothes and the male - particularly the working male - I am too gimped up anymore for real working, but long years have set the style and cut I wear. All of it is extremely durable, which translates to extremely uncomfortable and hard to break in.
I do admit that it puzzles me that people literally choose tattered clothes to dress up for an outing.
Rather, that one would pay such crazy money for the presentation of a caricature...
I'd wear those things for working in the yard. I keep a collection of scroungy clothes for exactly that.
I ain't ever *not* working... even now... And perhaps a difference in cultural norms... Here those wore out clothes only get wore out one way - And that's a badge of honor. Putting on airs is just that (no offense meant).
I'll tell you a little story about that... I was out cruising the fair one time with a townie buddy of mine, when he said, "Well, will you look at that!" To which I replied, "Oh yeah... She's right up my alley!" ... Or some such thing... The funny part is, evidently there was a bombshell redhead dressed to the 9's and strutting her stuff... A woman I never even saw, even though I looked right past her to a little strawberry blonde with her hair done in a horse-tail braid with a wore out straw hat kicked back on its straps... Not much makeup, if any, a regulation cowgirl shirt with pearl snaps and the sleeves rolled up, showing an ample figure and her well tanned forearms, short nails and calloused hands... Wore out jeans and worn out Tony's with full-ride heels and scarred spur channels rounded out the package, and she smiled at my interest through cornflower blue eyes...
All that spoke of honesty and work ethic. A horsewoman and cowgirl in no uncertain terms. She wore what she was without a doubt in my mind. And I dang near wound up marrying that gal. That's what I saw. Not the bombshell made of plastic and dye that my friend was looking at.
Maybe it's because I'm the descendant of dirt poor people who would love to have been able to invite guests to their house and live like "the rest of society." With no indoor plumbing and no money (and no government handouts), it just wasn't in the cards for them. Daddy only went through the 8th grade. He would have needed clothes and shoes to go to the school where 9th grade started. Guess who became a collector of shoes when he got out of Appalachia. 
He'd shine those puppies up, keep the heels in good repair, and line them up neatly along the wall of his closet. Nothing was expensive. Everything was comfortable. He was a well-groomed man who was thankful to be out of the poverty of his youth. He was a blue-collar shift worker, and I couldn't be more proud of my daddy. 
Dang well right.
But I retain that poor upraising... And honor it to this day. I ain't had thirteen-patch pants since I have been making my own way... But 'Use it up, wear it out, make it do, or do without' is still the thing that marks my way. And I wear that every day.
