This is sort of an expansion what I wrote before, but for guys getting into their groove of creating looks I always recommend a few things:
1) Imitate. Don't worry about being original until you have uber-confidence. When you imitate a look you like you'll feel more confident in it by default, and when you look confident in something you automatically look better. So while you find your style, imitate looks. It's how we learn everything in life.
2) Where to imitate from? Scour the street style threads across Fashionising:
Paris,
Italy,
Sweden,
New York and
London. Also keep an eye on our
fashion pictures diary, there are lots of great shoots and adverts to draw looks from. And check out the women's looks two; these days there are plenty of unisex stylings.
3) Find your style gurus. Who do you think dresses really well? Pick a socialite, a celebrity, a sports star, whomever. Then follow their looks online. Imitate and adapt.
4) Save all your key looks to your computer for when you're in need of inspiration. I've since moved my entire look book to my iPhone.
5) My killer tip for everyone: segment your wardrobe. Pick themes (I have a corporate section, a rock section, and a preppy section) and group all your clothes by those themes. That way as you dress yourself you're not looking at a mass of clothes, but can mix and match from a particular area of your wardrobe. You're essentially cutting out the confusion by doing this.
6) Constantly clean up your wardrobe. I always put my clothes into storage when they're off season, and I always keep a list of the key pieces I'm missing (or the accessories I could do with, inspiration courtesy the above picture and street style tips). When I buy, I do so to put them back with a particular theme and store it accordingly.