So look here's my situation. I need clothes regardless because most of mine are old or grungy but also trying to find something to suit my style. And though I find it a bit aggravating, some of female friends think I need to dress better if I'm to catch a girls eye. More color for one, unique style etc. But im a simple man. I buy clothes that are cheap and comfortable. That being said almost my entire wardrobe consists of black, grey, or dark blue.
For reference, I guess you could say my style is sort of punkish? Like maybe what metalheads wear or even what nerdy guys wear.
Do you have a friend that is well dressed and whose style you like? If so, you could ask them where they shop, or if they would go with you. I think you should only buy clothes you love, or else you won’t wear them. If you like simple, solid colours that’s OK, start with that and eventually add some different colour shirts (even solid grey or light blue or white would be a good addition to have) Go through your closet and drawers and put everything that you have not worn in a year in a bag for charity. Also put in everything that is worn out, stained or torn. Be ruthless. You may find things you forgot you had and that are still wearable. Freshen up any sweaters you have by washing them inside out and pulling off any pills (the little round things) Have a good look at your winter coat and boots to see if you still like them and that they are in good shape. Clean them up if needed. Then start shopping with the basics, since you need new clothes anyway. Start from the inside out. The first time you shop (online is fine if you know your size) get new underwear and socks. Then I would suggest new pants and shoes, and then two new shirts, one white and one black. It is better to purchase good quality clothing because it looks better and will last a lot longer, so spend as much as you can afford on each item. If you are on a budget, make sure to budget in one new item each paycheque or every other paycheque for an expensive item (like a coat or boots) Since you asked, I have found good quality items at H & M, Marks Work Warehouse and The Bay, always watch for sales of course. Value Village, the Salvation Army stores, and consignment stores have some excellent quality clothing for very affordable prices, but you have to take the time to go through what they have to find it. Check tags, anything that is mostly polyester won’t be as comfortable or last as long. Everyone should have one good formal outfit for special occasions, and a pair of dress shoes. You don’t have to change your style completely, make sure everything fits properly, this makes a big difference in how comfortable you will be and you will look better than in oversized clothes. Since you are used to grunge and punk some of these suggestions may seem foreign to you, but your style will naturally change as you get older and it’s important to feel good about what you are wearing. You can also mix some of your grunge and punk pieces with newer pieces. Once you do this, you will feel better knowing you are looking your very best, and that will make you feel more confident which will make you more attractive to others.
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