I think the whole point of this looks is basically buy things that are more time tested, things not looking like a advertising billboard. It isn't about dressing like middle age, great clothes doesn't mean wearing the latest trend or having the latest style.
The other thing is that you need to think so much more what you wearing as an outfit. Think like a girl more when dressing. You see all these girls, nice looking, nice dressed girls, they didn't just throw it on, even when they say so. They thought about what goes with what, colour co-ordinate, the right hat with the right coat, the right shoes with the right dress. As a guy, you should think what shoes go with what jeans, what jacket goes with what colour T-shirt/shirt. Take 5 seconds to look in the mirror before you go out the door.
Also, pay attention to ads more in magazines, pay attention to what looks good and it's not hard to replicate. Also pay attention to the cut, it's really rather important. Some brand cut a lot differently than others for the same style, get the cut that looks good on you, ask for a second opinion in the store.
Shopping can be fun! Lol