I don't think Mark would have any problem at all fitting in with the preppy guys at Bowdoin in the '50s. This is clean, classic, and simple New England collegiate style.
The great thing about this look are the fitted khakis. So many guys wear khakis that are way too baggy and really make a look like this sloppy instead of sophisticated and refined. Similarly, the shirt is also properly fitted. When it comes to guys, one of the biggest fashion mistakes are too-baggy oxford shirts. Whenever you go shopping always try an oxford shirt a size smaller than you think you would normally wear it and then work your way up. If the next size is too baggy then the size you tried on before is probably your true and proper size. Basically: if there is a lot of extra, unnecessary fabric when you tuck your shirt in, don't buy the shirt!
And of course, always pair your outfit with a well-worn book for the final touch.
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