If you were to just pick one top and one bottom that epitomizes prep style, An OCBD and khakis are the “go-to” looks.
From that foundation you can switch and amp up colors and still retain the preppy look. Keep in mind if you’r wearing a loud or bold piece, make sure the other pieces are muted to balance your ensemble.
If solids aren’t your thing, you can also go for prep patterns like gingham and plaid (or check). Like I said in part 1, the smaller the check the more flattering.
A short-sleeved shirt is more suitable for hotter climates. To avoid looking geeky, make sure the fit is is right; not too baggy (with flared or long sleeves) or tight (sausage fit). One way to look cool and offset the dweebiness is to roll up the sleeves.
As far as tucking in the shirt, I personally leans more towards yes, if you’re wearing pants. If you’re wearing shorts, and are in a more relaxed atmosphere, untucked and slightly disheveled is fine.
Polos are also the obvious substitute when going for comfy and cool. Traditional colors like white, navy and light blue are the usual standards. So as to not look too basic and boring, you can experiment with bolder, un-played out colors like pink or aqua.
Shorts have traditionally remained pretty basic and solid, with loud and pastel colors being acceptable. Plaid or madras have also been part of prep. Personally, a trend that I’ve been liking is the embroidered pattern. Not too ostentatious, but just a minor detail(s) that catches the eye and makes it distinctive.
If ever you need to dress up – for a debut, wedding, corporate event, etc. – it’s pretty simple to build on what you already have-prep-wise: Just add a jacket/blazer and tie. Navy is the most prevalent; for cool points, go for white or gold buttons. As far as pants, in addition to chinos, you can also go for dress grey. For ties, knit solids are ok, but repp (or stripe) is quintessential prep. Think American, or British, boarding school uniform.