I also hate to shop. When I buy clothes, I'm in and out, like a ninja. And if I had my way, I'd wear my jeans / t-shirt / hoodie combo every day for the rest

I also hate to shop. When I buy clothes, I'm in and out, like a ninja. And if I had my way, I'd wear my jeans / t-shirt / hoodie combo every day for the rest of my life. However, there's times when your clothes matter and your usual garb won't cut it. Want good service at a posh restaurant? Doing a bizdev presentation at an ad agency or media company? Getting deposed in front of a grand jury? You'll want to have a broader sartorial range. It's not about your self-esteem, it's about the (often unfair) reactions of others to your looks. I haven't seen the product, but a dress.me-like service could be useful here. In the past, I debated signing up for hendrickspark.com, an online personal shopping service, but I don't spend enough on clothes to get value out of it. Perhaps dress.me will be better suited for someone who only occasionally buys posh clothes.