T: I was struggling with it last summer.  I’m still torn now as I delude myself that summer is right around the corner.  I’m not sure if I’m the kind of guy who can wear white (non-sneaker) shoes.  I’m worried that I would destroy them after one night out.  Or, I’m worried that the guys on my rugby team would destroy me for wearing white shoes. 

If I was going to pick up a pair, it might be this one from Sperry which is currently on sale for 100 bones.  The gold detailing on the back is a nice touch too.  I’m going to make a decision soon…….

T: It’s been pretty balmy in beeeeautiful Philadelphia lately.  Today, I broke out my favorite pair of khakis for the beginning of another humid and muggy Philadelphia summer.  If you haven’t picked up a pair of weekend khakis, it’s about damn time you did. 

By “weekend” I mean that these pants should not be pressed down the front, should never EVER go near an iron and as god as my witness, they should not have any pleats.  Additionally, these pants should be on the trimmer side.  Think of the pants as a warm-weather alternative to your favorite pair of jeans (which we have blogged about ad-nauseum lately). 

There are lots of great options out there.  Some of my favorite options come from Land’s End Canvas, Gap, and Docker’s military inspired K-1 model.  But, if you have some serious dough to spend, think about the selvedge khaki from Blue in Green.  No matter what you decide, wear the pants well and never wear them to work (you don’t want to be reminded of the office while eating chips and salsa barefoot on your friend’s patio (as I am doing as I write this). 

Check out the picture below for how to pull it all together.

(khakis= GAP, v-neck=American Apparel, shoes=Sperry Top-Sider).

T: And that means that it’s time to break out my favorite piece of yachting footwear—the boat shoe.  Boat shoes normally have a white rubber sole so you won’t scuff or slip on your boat (or on your way to the subway).  They are also the only leather shoe that actually looks better when you get them wet. 

For my money, no shoe is more versatile when the weather turns warm and one no longer feels the need to be chained down by the tools of oppression known as socks.  But, if you are going to go sockless, make sue you invest in foot powder or your boat shoes won’t last the summer. 

Boat shoes can be worn with jeans (make sure they are on the tapered side so the shoes don’t get swallowed up), khakis, khaki shorts, or seersucker.  They also are the only shoe that can take you from a summer day at the office to the beach to a nice outdoor summer dinner.  Andrew and I both own this pair of brown Sperrys (above) which can be purchased from jcrew or sperrytopsider.com

So go out, treat yourself to a pair of Sperry Top Siders and pretend that you are “On a Boat” with your nautical theme pashmina afgan.