75% comfort & utility 15% formalities & style 10% drugs, alcohol, wedding rings, embarrassing self baby portraits (imagine that scenario: “Hey Anon, want to see baby pictures of your girlfriend?” you: “not really. want to see baby pictures of me?!”) and then some other stuff, like a straight edge razor or other ‘safe for travel’ paraphernalia.
but seriously, lets get serious, not like third date w/ no kiss serious, more along the lines of met-at-a-bar-two-weeks-ago-decided-via-facebook-chat-to-get-coffee-serious.
I’ve finally gotten my weekend trip packing shenanigans down to a science:
Chicago is pretty frigged currently, so layer up and make those bro’s over at haberdash recognize the ‘tourist’
—- # of days x undergarments + 1 (briefs, v necks, thermals, socks etc.)
—- # of days x button up shirts -2 (versatility and timing are key here, the only fresh & crisp shirt you’ll be expected to present is for that dinner, the others you can get a wear or two out of. if you’re like me, you might want to make that omission of -2 shirts -1, or just convince yourself spilled beer adds “character”
—- 1 pair of fitted dark denim, 1 POC (pants of choice) - you know what fits you well, go formal (for dinner) or whatever. i trust you. don’t blow it bro!
—- 2 sweaters, preferably cotton or a wool cotton blend. those cashmere & pure wool numbers don’t hold their shape after a full day of chitown gymnastics.
—- 1 blazer - because, come on. we’re not barbarians….
—- a coat, because this.
—- 2 pairs of shoes. (formal joints & your most comfortable shoe/boot that’ll hold up to some light snow or rain - wear these when you travel)
—- a few accessories - 1 tie, 1 scarf, 1 watch, 2 belts, a pen (always) and a couple business cards (not your business cards- hah)
—- a good bag:

—- a good handshake, a good disposition and the removal of the word “no” from your vocabulary. (within reason)
also, a couple friends said i should forward you to kuma’s corner for a solid chicago burger.
the rest is up to you anon, again - i trust you. she trusts you. have a safe trip. bring back something interesting and send me a picture from the aviary.
-dillon.
