Saturday, October 23rd. Harry's Bar and Tables, Westport.

Paige, from M&S Grill/McCormick & Schmick's, Mixologist.
Paige has great taste, and good thing it is not limited to cocktails! I LOVE this look, especially in the context of the environment. Harry's patio is wonderful; full of character and style. I love the brick, wrought iron gates and tables, and the big red caboose/bar.

This look is a pretty good primer in the best Harry's has to offer: easy-going, fun, old-school, classic, sexy, and dash of masculinity where it counts (at Harry's it takes the form of a handsome and friendly bartender, in Paige's outfit the brogues have it).


These are my new favorite style of shoe. Brogues are hot because they are a stark contrast of what a usual sexy shoe looks like (tall, thin, 4.5 inch heels). You can wear them with just about anything, and they aren't sweet or mild mannered. This shoe adds a punch, and the color says "HELLO FALL! HELLO PILES OF ORANGE AND RED LEAVES! HELLO BACK-TO-SCHOOL TIME! HELLO HOT TEACHER!"

This is Caitlin, to be referred to from here on as Hot Pants. Normal people don't usually look good in hot pants, short shorts, daisy dukes, or any other form of glorified underwear. But Hot Pants is far from your everyday Joe. For starters, she rides her bike everywhere, which puts her in the main category of people who can wear hot pants- athletes (i.e. cheerleaders, runners, male swimmers, etcetra).

This outfit is on the ballot for my favorite of October. Here is why:

whistle on a chain

Nikes with red and gold laces

The individual elements of this outfit are so extraordinarily personal, and crazy, and cool. It's kind of ridiculous because she really looks as though shes about to whip a cheerleader squad into shape, blow that whistle and demand MORE SPIRIT FINGERS. And who's going to argue with a girl in a black leather jacket and hot pants?

Earlier in the day I had watched The Buddy Holly Story starring Gary Busey (yeah, Gary Busey in 1978 kinnnnda looked like Buddy Holly if you put him in the right glasses) and when I walked past this guy his glasses caught my eye.

early Buddy Holly glasses
Jon is studying to be an urban planner. Um hum.

Sophia at Santora's Pizza.
Also spotted a tee full of attitude at the late night pizza shop. Sophia, the doyenne who maintains order and decorum in at the 3am eatery the size of a walk-in closet probably has no problem with haters, hence the shirt.