However, changing my wardrobe has proved to be a problem. I'm a horrible shopper, and I don't know what looks are stylish/attractive/sexy/etc. Naturally, I've tried asking a bunch of my female friends and relatives to help me shop for clothes. However, the only person who is willing and able to do so is my mother. While she means well and thinks she knows what's in, she's really out of touch (actually insisted several years back that bowling shirts were "in" for guys in their late teens/early 20s.) Somebody who's that out of touch can't be trusted in helping me pick out good clothes.
Since I now wear a smaller size and want to wear nicer, more physically-attractive outfits, but have no sense of style and nobody to help me shop, what should I do?
Most Helpful Guy
Head over to mens warehouse, the people there are generally friendly, can help you out with measurements/tailoring clothes to fit to you, and sometimes (the only times I guy stuff) they offer buy one get one free. Buy an 80 dollar shirt? Get one free. Keeps things affordable for those of us operating on a budget.
A base style that works for most occasions: Dark Jeans, button up dress shirt preferably solid color like a black or gray, light blue, etc. or you could go with stripes as well, and make sure you're not wearing sneakers. Sneakers are for working out. Get some decent stylish shoes. Something nice, because if you get low quality shoes they will kill your feet and you'll hate them. Get good quality shoes and you'll feel like you're walking on clouds haha.
It doesn't hurt to have a dinner jacket or two in case you go out somewhere nice. Also, I sometimes like to throw in white t-shirts under the dress shirts. It's nice for two reasons. First, if you sweat and have no undershirt, it's going to be visible on the dress shirt. Not a good look. Second, if it gets warm or you're out and say want to throw a football around with somebody or something, you can take off the dress shirt. You don't want to be doing physical activities in a 90 dollar shirt do you? No. So wear an undershirt when possible.
If the summer months get pretty hot, get some solid color t-shirts to replace the dress shirts in casual settings. Sometimes even a dress shirt is just a bit too much. (there are some dive bars I go to where a simple dress shirt would feel just "too" dressed up).
Like I said, go to mens warehouse. Buy one get one sales will prevent your wallet from being mauled and the staff will help with sizes/tailoring jackets to you.