Get a woman who isn't your mom to pick out your clothes
Having a woman take you shopping's risky -- sure, she may know more about clothes than you do, but what if you ask her for Adidas and she buys you Zips? What do you do then, Will Smith?!?! For clothes advice from
Will Smith's mom a chick who knows what she's doing and won't ruin your rep, check Haberdasher.
Haberdasher's a just-launched men's styling service from two consultants who realized they had no idea what to wear when they met with fashion clients (wait, wait, wait -- Big Johnson is out?), so they started asking female friends for advice, and then decided that they could use their newfound expertise to help other schlubs like them out. It works like this: enter your basic info, and within 24hrs you'll get a call from one of their stylists (not that you care, but all of whom are cute girls who've worked on TV shows or for celebs); from there, your new lady friend asks you about your needs (Do you wear ties? Do you go to clubs? Do you really need to keep that Big Johnson shirt? etc.) your measurements, and your color preferences (definitely make it clear that you prefer In Living). From there, it's your choice whether to shop with her or just have her pick stuff out, with each stylist compensated hourly instead of getting cuts from boutiques on each purchase, meaning she'll actually be more likely to go to whatever stores make the most sense for you, so here's hoping you enjoy all that new ish from Hot Topic.
The whole thing works on a $100-per credit system, and, with the code THRILL, you'll get one credit free, leading to your first batch of clothes, which is cool since here's the situation -- you can be sure to show them off on your next vacation.