I've never liked shopping for clothes. When I was younger, I always went with a parent and just wanted to get it over with. When I was out of high school, I would always go with somebody else. Then after I got married, I always went with my wife. All my life, shopping for (my own) clothes is something that I've had to be dragged along to do. I would wear worn out clothes rather than shop for new ones. Since developing or discovering my trans feelings*, I've basically stopped shopping at all. All new clothes that I own have been brought home by my wife on one of her own shopping trips. The only new shoes I've bought for at least two years have been steel-toed shoes for work.
My sister is getting married in two weeks. Obviously, female clothes would be inappro(my therapist joked about going en femme to the wedding). So, it was decided by my family that I need new dress clothes, for the wedding, and because I'll "need them for my teacher program". I went out shopping with my sister on Friday to Sears and ended up with dress pants and a shirt. Male dress clothes are really boring. Essentially there are only a few variations on a theme. It was difficult for my sister and the lady helping us because I had no opinion other than I wouldn't get a white shirt. I swear they spent like fifteen minutes holding up ties to this one maroonish shirt that they had picked out, but they were unable to agree on one.
Plus male dress shirts fit poorly. Presumeably most readers will know this, but there are basically two measurements that are used to fit a men's dress shirt: neck size and arm length. Apparently I have a fat neck: 15.5". My arms are 33". Anyways, with only the two measurements, the manufacturers assume that I have a big chest and arms. So that means that the arms and chest are always really baggy. (Yeah, I know that a tailored dress shirt will fit better)
The next day my sister took me to another store for a tie, and another store for dress shoes which "were supposed to last me for years". These were "nice" leather shoes that cost $180!!!
My parents paid for these clothes just because.
On the positive side, I have lost a bit of weight. I was able to buy 32" pants for the first time in a while.
*topic for another post: were my trans feelings latent or created??????