For particulars, as a woman I've always thought men look good in almost any situation wearing casual collared shirts covered with lightweight fitted vneck sweaters, comfortably loose but not baggy soft straightleg jeans or khakis or gray pants (please stay away from tapered legs or pleats! they should fit so they sit comfortably above your hipbones, "sitting" being the operative word- not so loose you need a belt or have large hanging gaps fabric, but loose enough to look smooth not clinging/pulling anywhere, long enough to touch the tops of your shoes), and dark but not dress shoes, not too heavy/boxy (take a look at sketchers for ideas, though I've always found they're sadly leather). The glaring white tennis shoes can make otherwise good outfits look middle-aged-American-tourist. And I definitely second the idea of a haircut!
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