1. Looking at photos is not the same as looking at the real thing;
2. Clothes are more than just the look. How they feel is also important;
3. You obviously can't try clothes on online. You can (and really need to) in a store. I have clothes that fit ranging from M to XL depending on the brand and style.
So there are those barriers to overcome. There are additional issues.
First, I read the dress.me blurb and it says that when you signup it asks you several "this or that" questions. A theoretically reasonable approach but one doomed to failure.
The reason is that people (men in particular) don't know what suits them. When someone says they like something, it means they're accustomed to it. This is a key point service providers like this need to understand.
It's why you see people seemingly trapped 10, 20, 30+ years ago with their haircuts, shoes and clothes. Typically this is how they looked and what they wore when they were teenagers and in their 20s. That sort of thing sticks because it's what they knew growing up (much like musical tastes tend to be) or even it's just the nostalgic angle: that style takes them back to probably what were more easygoing days.
Second, there are an awful lot of men--we geeks are particularly guilty of this--who have a completely utilitarian view to pretty much everything, including clothes. There's a reason the programmer stereotype is t-shirts and jeans. These clothes are comfortable, require very little maintenance, are cheap and require very little thought.
Clothes, like many things, are a statement about who you are as a person. Pretty much everything we do is some form of expression of who we are. This is even true of things like programming language choice.
So the problem we geeks have in particular is that we don't generally care about what kind of statement our clothes make, which in and of itself is a statement.
Anyway, watch any of the makeover shows that are on TV. Whether they be for men or women you will see the first thing the self-appointed style gurus will do is beat them out of their old habits into things that actually suit them. Asking them what they like would get you nowhere.
This is also why the cliche exists of women shopping for men. I think women are probably more naturally inclined to the "group" aspect of pretty much all forms of self-expression, clothes being just one. Just watch a woman--particularly a young woman--get dressed for anything and you'll quickly realize it's a group not a solo activity deciding what to wear.
Sites like this I think are seductive to those who start them, much like dating sites are. It seems like it should be easy, right? I think the reality has proven and will continue to prove otherwise, at least until these fundamental problems are somehow addressed.
The true meaning of "I hate shopping" is more likely to be "I hate making decisions about things I don't know about, care about or both." The "knowing" part can probably be fixed. The "caring" part is a much bigger problem.