how can we dress so that in, say, 15 years we don't look back on this time and think, "barf... what was i wearing?" it's a tricky idea. how can you look current and up-to-date yet timeless at the same time?
well, look at what has always worked throughout the years:
camel trench, leather jackets, jeans, ballet flats, aviators, crewneck tees/sweaters,
blazers (sans shoulder pads), structured pants, simple heels, button ups
notice: these are all basic BASIC things.
personally, i think the key to looking cool and classic is to have that solid "basic" base.
then add some flair! a bright scarf, a fun hat, some chunky jewelry, a statement shoe, up-to-date hair...
whatever you want.
you can look classic while still being you.
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