We’ve been slowly but surely getting into the heart of spring and summer style here on The Style Guide, and that means one thing: Focusing on warm weather essentials that are going to help you conquer even the most tricky seasonal style situations. Think of a decidedly casual spring or summer Friday in the office (or perhaps … working from home?). What are you wearing? A one-size-too-large polo and khakis that probably don’t fit as well as they should? Not if this #OOTD has anything to say about it. Even when it comes to “Casual Friday,” there are ways to rise to the occasion while still keeping things toned down and office-appropriate. For instance: We’re ditching the polo or overly casual graphic tee in favor of a stylish short-sleeve shirt from Style Guide pals Taylor Stitch, and we’re swapping those khakis for slim light wash denim and classic suede chukkas from a timeless brand (that’d be Red Wing Heritage). Along the way, we’ll accent this ensemble with durable accessories, including a stylish casual watch and a work week-friendly leather messenger bag. This ensemble just gets it done if you happen to work in an environmen that, like so many offices nowadays, leans more and more laidback. Rethink the way you dress for summer … starting right now.

A breezy, West Coast-inspired short-sleeve shirt pairs up nicely with suede chukkas and casual office essentials.

• The Shirt: Taylor Stitch Short-Sleeve California Shirt in Navy Poplin, $98 — This isn’t like Dwight Schrute’s short-sleeve shirts. The California Shirt in Navy Poplin is tailored and classic — perfect for the office.
• The Denim: Standard Deviation Beta Denim in Light Indigo, $98 — These slim Standard Deviation jeans strike a nice balance between being overly faded or overly heavy (like indigo selvage denim, for instance).
• The Belt: Levi’s Aberdeen Belt, $38 — Leave it to Levi’s to make a stylish leather belt that’s neither too casual nor too dressy — again, the perfect middle ground for a Friday in May … or June, or July, or August.
• The Chukka Boots: Red Wing Heritage Weekender Chukka, $230 — Ditch the dress shoes for a day — the comfortable, durable and casually stylish Red Wing Heritage Weekender Chukka just works.
• The Socks: Arvin Goods Crew Socks, $10 — One of the best parts of spring and summer? Rethinking your sock wardrobe. Gone are those heavy boot socks — enter these crew socks, cut shorter for casual style and a cool breeze.
• The Watch: Redux Courg Watch, $319.98 –Don’t worry about matching your watch strap to the color of your belt or shoes here — the Redux Courg Watch means business, in the most rugged and laidback way possible.
• The Bag: WP Standard Vintage Messenger, $295 — The handsomely crafted WP Standard Vintage Messenger has more than enough space for your laptop and every single one of your everyday carry essentials.
• The Sunglasses: Komono Luca Sunglasses, $119.95 — Sunglasses are a somewhat underrated finishing touch, and the right pair — like the Komono Luca Sunglasses — add just enough casual flair to a cool ensemble.

The key to pulling off a dressed-down Casual Friday ‘fit starts with … well, fit. The California Shirt in Navy Poplin from Taylor Stitch is a prime example of the right way to do a short-sleeve shirt at the office. It can be worn untucked thanks to a length that’s just right. The fit is nicely tailored, the fabric is classic and the stripes are a spring-friendly (or summer-friendly) touch. Yes, the California Shirt in Navy Poplin is but one element that puts this #OOTD over the top. Pleasingly faded light wash denim works quite well alongside the Red Wing Heritage Weekender Chukka, thanks to the casual vibe of both pieces. Levi’s serves up the rugged Aberdeen Belt, which contrasts in a cool way with the Redux Courg Watch for style that fits in at the office and at happy hour. I’d be willing to bet that no one else in your office has the Komono Luca Sunglasses, which is what makes ’em such a cool pick for this particular #OOTD. And when it comes time to hit the road — both heading to and leaving the office — the WP Standard Vintage Messenger should certainly come in more than handy. To recap — you can make a short-sleeve shirt work at the office in a casual setting, as long as you nail the fit and fabric. Again, the California Shirt in Navy Poplin from Taylor Stitch checks off all the right boxes. It’s up to you to power through the work day now.

Folks, what do we think of this #OOTD? Will you be trying this slightly bold look out at the office this summer?