Clothes make the man. When it comes to James Bond, it can also be said that clothes make the spy. Because of the longevity of the Bond film series, we can easily see the evolution of the fashionable modern man through Bond's suits and accessories.
The Sean Connery Bond of the 60s and 70s had costuming done by a British tailor. The early suits reflected the time and weren't particularly edgy. Single-breasted in blues and grays, Bond looked great, but you could still tell he was a government worker. In the later part of this period, we get more variety, and Bond's clothes more reflected the times with wider lapels, more brown and the occasional casual look.
When Roger Moore took over the Bond role in the 1970s, Bond's look changed again. Gone was any hint of trendiness (less brown, narrower lapels.) This Bond was all about being a classic. Here, we begin to see Bond in both single- and double-breasted jackets. Sport coats and yachting looks also entered his wardrobe. Bond no longer looked like a government operative but more like the rich playboy he often pretended to be in order to get the criminal and the girl.
*Timothy Dalton*'s brief stint as Bond was the first attempt to make Bond more rugged. Gone was the high fashion (except when he was wearing a tux.) This Bond was meant to be rough and tumble. The concept and the look never quite worked for the franchise though, and Dalton was quickly replaced with Pierce Brosnan, who revolutionized Bond in subtle ways.
Brosnan's Bond was a world traveler, and it showed as he was now dressed in Italian suits from Brioni. Casual linen looks were also popular for this Bond, and Brosnan succeeded in blending the slickness of the Moore portrayal with the manliness of the Connery-era Bond.
Daniel Craig currently portrays the sixth incarnation of Bond. He's perhaps the most physical actor that's been in the Bond role, doing many of his own stunts and reportedly being repeatedly injured on set. The wardrobe department has offset this bulkier Bond with a dark, conservative, very British look, which Craig somehow manages to make edgy, and casual clothes in light neutral and earth tones to accommodate many of the action sequences.