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Fun fact: the perforated holes on Oxfords are called brogues. Anyone who refers to the entire shoe as a brogue is technically wrong (the things you learn in design school...)

simplypi src - sharp gray blazer, though I've never been a huge fan of quilting on tops, this is nice

Cowlneck tee, high waist pants and structured jacket - Anthropologie - The Cheap Chica's

John Varvatos Official Site: Shop Online , VARV-3553 Fleetwood Lace Boot, johnvarvatos.com

Nice jacket, watch and tie combo. What color pants would you wear with this? I'd go with the same color as the tie......with similar color shoes...

Quilted tailored jacket with houndstooth detail

finally, chukkas that don't look like they're just for douchebags (crosby chukka john varvatos)

Doublju Mens Jacket with Button Detail GRAY (US-XL) Doublju,http://www.amazon.com/dp/B006WFG4SY/ref=cm_sw_r_pi_dp_RhLdsb112VVY53V4