Outfit Post - Dressing Up and Dressing Down

My girlfriend and I have been taking advantage of a service called HowAboutWe ever since I bought her a subscription as a Christmas present. I may do a longer post detailing the awesome perks, since we've been loving it so much, but the short story is that they curate events (or for the couples version, which we signed up for, 'dates'), that can include discounted or exclusive activities, hook you up with a reservation, and voila, next thing you know you're in a new brandy distillery in Chicago watching apples being smashed(?) by a man on a bicycle.

Really, it's been a great way to get us out of the house on the weekend when the weather says to just stay on your couch! Not only does it give my girlfriend and I even more quality time to spend with each other, it also has given me lots of opportunities to exercise my wardrobe by freeing me from my weekday business casual without taking me the whole way down to lounge-on-the-couch casual.

For example, we were back at it again this weekend with a quick trip down to NOSH food festival/farmers market, and I ended up rocking a great balance between the sharp style I like to exude and the more rustic, well, farmers-market-friendly options:

To start off, I love to wear a shirt and tie, and blazer when I can. However, going into this, I knew that coming in a pressed white shirt, silk tie, jacket and chinos probably wouldn't only not fit the crowd, but would also end up getting something spilled on it. So instead, I made some conscious choices to dress down my standard 'fit to something that would work great in the circumstances.

First, I went with generally rougher and more casual fabrics. Instead of a poplin or white oxford shirt, I rocked a plaid, heavier cotton (almost flannel) shirt. For the tie, I went with cotton knit instead of a shinier silk knit, and for the blazer I left my more constructed and sleek options at home, instead grabbing an unlined, soft-shouldered wool twill.

I even made the same general effect with my shoes...these boots are pretty sharp, definitely no shit-kickers, but the suede leather, as opposed to polished, takes things farther into casual territory, as do the lugged soles, which also came in handy walking home through the slushy mess that spring is bringing us.

On the other hand, a few details kept me feeling like I was still on the top of my game. The shirt, for example, while full of more casual details, is actually one of my custom shirts, so the fit is perfect (which will instantly have you feeling like you look 100%). I kept the tie clip, partly because I didn't want my tie falling in my food, and again, because it keeps a sharper edge to the whole look. Last, while I did pick jeans (like a farmer, eh?), I kept them slim and dark to keep some sharp lines from top to bottom. I also decided to go ahead and rock a pocket square (always a bit of a dandy move), but even kept that on the more casual end of the spectrum by picking a cotton, 'bandana' square in a spring-appropriate green that would compliment but not match the green tones in my shirt.

Last, I maintained the balance by throwing a casual waxed cotton jacket on top. No sense in building that careful balance, only to cover it all with a more formal overcoat. Lucky me, the olive color of my jacket worked great with the blues, greens, and greys making up the outfit so far.

Outfit Details:
Blazer - Frank and Oak
Plaid Shirt - Custom by Modern Tailor
Cotton Knit Tie - J.Crew
Cotton Pocket Square - J.Crew
Dark Blue Jeans - Levi's 513
Suede Boots - Polo Ralph Lauren
Waxed Jacket - Frank and Oak