Outfit Post - Saturday at the Dog Park

We finally had an absolutely beautiful weekend here in Chicago, so Christine and I took advantage of the weather and took a long walk to Wiggly Field (yes, that's the official name) with our puggle, M.C. Hammerpants (yes, that's his real name). As we were walking, it dawned on me that I rarely post really casual outfits on here, and most of what you see of me is in my work or more dressed-up weekend duds, so I figured this would be a good chance to feature a really laid back (but still sharp) look:

If you'll recall from my list of summer style goals, I decided recently that I wanted to start wearing chinos more in a casual setting, as opposed to turning to denim every time I'm off duty. I grabbed these Alpha Khakis from Dockers with just that in mind...the bright color is a little bit much for my law firm day-job, but it's a perfect summery punch of color for a weekend look. I love the fit of Dockers Alphas, but they are just a tad long on me. Since I haven't had the chance to hit up the tailor with these, I rolled the cuffs, which added an extra casual vibe to the look and emphasized the bare ankle (one of my favorite parts of summer).

Up top, I picked this striped tee that I got during the last big Bonobos sale for about $10 (similar here). Not only was it a steal, but the blue and white stripes give a nautical vibe that is very on-trend for spring (and summer, and fall, and pretty much all the time except dead winter). I really like it in this combo as an added bit of color that stays neutral and subtle enough to not come off as clownish in combo with the bright pants.

I also said I wanted to step up my summer footwear game, and I'm in the process of doing so with some Jack Purcell's on the way from Mr. Porter. Meanwhile, though, I really can't go wrong with my Sperry Topsider boat shoes. I picked these up last summer and wear them all the damn time and they just keep getting better and better. In fact, I used to be really OCD about keeping my kicks pristine, but after these got covered in mud at Lollapalooza, I kinda accepted their beat-up-ness and since then have really come to love the personality that some hard wear can give a pair of shoes. I'm also rocking a pair of Pact No-Show loafer socks, which I consider a must-have for the summer, and allow me to kick it sockless without worrying about gross, stinky feet and shoes.

Last, as I was stepping out, I realized it wasn't quite as warm as I thought, especially in the shade. Instead of bringing a light jacket, which honestly would have been a bit much and I would have ended up carrying most of the day, I made a smart choice by throwing on this Frank & Oak OCBD. It's one of my favorite pieces from F&O (you all know my love of an OCBD by now), and I wear it all the time, whether it's to work with a knit tie and a blazer, or on the weekends with jeans and some Chukkas. Here, I took it to new territory by kind of using it as an extra-light jacket. While I normally steer clear of the untucked and unbuttoned look, using this as a jacket let me lighten up on the sartorial 'rules' and embrace the laid-back nature of the look (and the gorgeous day).

For accessories, I topped things off with my brown braided leather belt, which has become my favorite thrift-store find. I literally spent about a dollar on it, and I think it's become a signature part of my style (more on that later). The Form*Function*Form watch that Christine gave me last year was the perfect finishing touch, and was a spot-on match for the brown leather of the belt and shoes. I love that this watch straddles the casual and at least semi-business line very comfortably - I'll wear it with jeans and a Tee one day and with a dress shirt and blazer the next. Versatility is key, my friends.

Anyway, ended up really happy with the 'fit, and had a fantastic day - we hung out at the dog park, took a leisurely stroll home through Lincoln Park, stopped in for cocktails and bacon-wrapped dates (and some treats for the pup) at a neighborhood cafe, and just soaked in the summery Chicago vibes.

How do you relax, sartorially? Do you have a go-to casual look, or are there new trends you are trying to work into your rotation? Share in the comments!

Outfit Details:
T-Shirt: Bonobos (similar) (use our referral link for $25 off)
OCBD: Frank & Oak (use our referral link for $25 off)
Chinos: Dockers Alpha Khaki
Shoes: Sperry Topsider (Editors Note: You can grab these on sale right now at Nordstrom for just $60. Great deal, I'm grabbing a pair if I can).
Socks: PACT No-Show Socks
Watch: Form*Function*Form via Huckberry
Glasses: Grant frames by Penn Avenue Eyewear
Belt: Vintage Thrifted, suckas.