WIWT - 6/4/2013 - Classic summer prep on a cooler summer day.

The weather here in Chicago has been so wacky lately that it's been really hard to dress seasonally. It seems to always be either hot and rainy, or cool and sunny. Today fell into the latter category...the gorgeous sunshine and clear blue sky have me thinking summer, but the temperature would be more in place in March or April. Today I really stepped up to the challenge and embraced the cheery look of the day while keeping myself warm enough for the unusually cool breeze.

The biggest thing I did here was combine very light colors with my pants and shirt. In general, this is reserved for warmer summer days. I actually just read an article today in which the creative director and CEO of Grenson  shoes decreed, as a Style Rule, that men should never wear a light shirt with light pants unless the temperature is 85 degrees of higher (or something like that). Personally, I don't really adhere to the strict temperature requirement, but I do like to hold these combinations off for brighter days (it looks pretty out of place in the winter or on a dreary, rainy day). However, instead of reaching for my lightweight shirts, I stuck with a heavier OCBD from Frank and Oak. Boom, perfect balance between form and function. I also went with a lighter brown belt to add to the brighter motif, and the pants are a very light khaki chino from J Crew.

Down to the shoes, instead of going sockless in my boat shoes or tan loafers (which I've been loving to do when the weather permits), I went with my darker Tod's loafers. They aren't too chunky, so they don't clash with the more summery vibe, but they are a little sturdier and, more importantly, fit best with thicker socks. Once again, an item I wouldn't normally be incorporating into a 'summer' outfit, but that works perfectly in this situation.

I topped it all off with my lightweight Uniqlo blazer. I probably could have gotten away with wearing a wool jacket, but it's not cold here, per se, just a bit chilly in the shade and when the lakefront breeze kicks up.

The lighter cotton/linen blazer is plenty as an just an extra layer throughout the day, and with the unstructured design is a little less bulky to be throwing on and off as the temperatures fluctuate throughout the day.

As a whole, this outfit combination is a great example of classic prep. The light khakis, OCBD, blue blazer, and brown loafers all fit the bill perfectly. I kept the accessories simple too, with a thin brown belt, brown watch, and plain white pocket square. Pretty much my only break from traditional prep is in the knit tie, but this tie has become a favorite of mine for just how versatile it is, and it goes great with this look as well.

Long story short, it's important to consider both style and functionality when dressing for the day. As tempting as it was to wake up and go all-out summer with my attire, it would have left me uncomfortable and chilly, and honestly would probably have kept me inside most of the day. Instead, with a few quick substitutions I managed to stay fly and warm. But really, Chicago, where is summer?

The Details:
Cotton/Linen Blazer by Uniqlo
OCBD by Frank and Oak
Tie and Tie Clip by The Tie Bar
Belt by Levi's
Chinos and Socks by J.Crew Factory
Shoes by Tod's (via eBay)