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)

WIWT - 5/16/2013 (a.k.a. Trying Something New)

So, for this look, I was busting out a bunch of brand new summer-wear items that have been recent additions to my wardrobe. This outfit is in no way 100% ideal, which is actually why I wanted to share it. First, the outfit:

I just bought this lightweight, cotton/linen blend blazer from Uniqlo after I visited their store in NYC and got to try a few things on for a sizing guide. Now that I know what fits, I will definitely be ordering more. This jacket is going to be my savior this summer. I've become so accustomed to wearing a blazer over the past several months, and don't really want to break the habit just because it's summer. However, even in my light wool blazer, the full lining has had me sweating even on just warm days. This unlined jacket, however, is light and airy enough to keep me cool even as we hit those Chicago heat waves.

Under the jacket I wore my custom Modern Tailor shirt (review here). As I've been wearing it more, and going back and forth more between this custom shirt and my other off-the-rack shirts, I've been appreciating the incredible fit more and more, and am definitely springing for a few more MTM pieces in the near future. Once again, feel free to use my Modern Tailor referral code for a sweet $20 off your purchase.

I also went with this dark red (I think they called in 'wine') knit tie from The Tie Bar. My love of knit ties just keeps growing and growing. Not only were they perfect in the winter as something with a little more heft, the looser weave also works great in the summer with your lighter clothes. This wine color too was not something I expected to go with everything, but somehow it really does. I find myself reaching for this tie multiple times a week, and I have a collection of options that's not to be sneezed at. Silver tie bar finishes the picture.

I also just bought these blue lived-in chino's from Gap. Somehow, between some crazy in store sale prices and discounts from signing up for Gap Card, I got these and one other pair for a grand total of less than $25.00. I practically danced home. I'm not a die-hard Gap fan, but their chinos are so damn comfortable. I grabbed these light blue ones to put a little spring color into my business-casual attire without being too in-your-face with go-to-hell pants.

I finished off the outfit with my new blue suede shoes by Bass, courtesy of an eBay steal. I've worn these once or twice casually, and wanted to try to work them into a work outfit and though this was a good outfit to experiment with. Here is where I wish I had made a few changes. I do love the shoes, and think they go well with the rest of the ensemble. However, the white/off-white laces lend to a more casual look. I think next time I'll try out some colored laces if I want to add a little more pop, or something darker, maybe even black, for something a little more muted.

Also, I had hoped that my sock choice would contrast with the shoes and tie in with the pocket square (a grey chambray number from Frank and Oak). Unfortunately, they kind of blend with the shoes in color, and I like my socks to really pop, so I'll try something else next time.

And there's my message is for this post. It's perfectly fine to make mistakes. Especially when trying out new things (I'm still working on my summer attire, as well as colored pants at work, for example). If you find something you think you like, just go ahead and try it! Unless you're a celebrity or a model or I don't even know what, the people in your day-to-day life shouldn't give you grief over some uncoordinated socks, or a non-matching tie. On the other hand, recognize what does and doesn't work, see the changes you want to make, and apply them as you pick out your clothing combinations in the future. It's all a learning process, and it's not fun unless you go outside your comfort zone from time to time. Also worth noting, while I messed around with colors in my pants, shoes and socks, I kept the rest of the outfit gloriously simple. Can't ever go wrong with a white shirt and navy blazer, and like I said, that dark red tie goes with everything.