One argument against the idea of timelessness in style is that everyone looks at least a little ridiculous in old photos (maybe not everyone). Why try to wear trend-proof clothing if it doesn’t really exist? But even if your choices weren’t always wise, a record of what you wore and how you styled yourself can be in retrospect enlightening, even inspiring.
One such record I’ve been enjoying is What We Wore, a crowd-sourced archive of photos–proto-selfies, portraits, passport shots, etc.–that aims to catalog style in the United Kingdom from the 1950s on. Each photo or photoset is accompanied by a vignette explaining what was going on at the time. These personal shots provide a nice, gritty contrast to the more glossy style histories you might glean from magazines or films of other eras. I also appreciate the cultural and temporal cross-section it provides: 1990s ravers share the page with early mods or families in the 1950s. You can tell that most of the subjects though they looked mighty sharp at the time.
–Pete