I typically where a lot of polo's or AE and hollister t shirts, and usually wear north face sweatshirt (like in my pic), or a Columbia jacket over it when it's cooler. So do I dress pretty good, or should I change my look?
Most Helpful Guy
Sweatshirts typically aren't going to help you, especially if your goal that evening is to meet an interesting woman. I'm assuming this is your goal as you're looking to change your look. I promise you, you will blend in with the crowd and it won't help you. At the same time there is never a need to dress like a clown. Outrageous / flamboyant jewelry and accessories will also be seen as goofy and will have the same effect. however, a happy medium is definitely an improvement. I suggest one interesting accessory, ex - a stylish watch, bracelet, necklace.
I would suggest the following.
1. Begin working out. Trust me, it will only make you feel better about yourself and you WILL look much better in your clothes. if you're looking to get on a workout program, message me and I can direct you to a few at home products I really enjoy.
2. When losing a bit of weight, buy tighter fitting clothing. Too tight screams "I'm probably gay". A little bit less than too tight screams "I'm confident in my own skin"
3. As the other women in this thread alluded to, simple is generally better, BUT I would stray away from exclusively AE / Hollister polos. If it were a friday night for me, I would wear a sweet looking graphic tee ( check out the buckle, or express ). make sure it fits you, and ask the females in the store to judge. they will know best. depending on the season you could wear cargo shorts or jeans (depends on the time of year)
4. Smart Shoes ( make sure they match your belt and socks).
5. Finally I would check out the book "always talk to strangers" by david wygant there is a chapter in the book dedicated exclusively to your question.
hope this helps man. feel free to let me know if you have any other questions.