Notes: Head here for the original, full in-person review. Also note that the 30% off code SHOPFALL is set to expire tonight, Monday 9/15/25.
About the Author: Adam Terry is a thirty-something sales manager in the construction industry. He enjoys fine watches, raw denim, boots/shoes, and working on his dad bod father figure.
Bonobos Jetsetter Unconstructed Italian Wool Blazer – $400
J.Crew Broken-In University Stripe OCBD – $68.60 w/ SHOPFALL ($98)
J. Crew Broken-In Straight Fit Chinos – $98
American Optical Sunglasses – $260
(cheaper sunglasses: Kent Wang – $55)
Citizen Tsuyosa Automatic Watch – $475
Boardroom Over the Calf Merino Socks – $19.50/pr
J. Crew Italian Suede Belt – $98
J. Crew Lake Shoes – $138.60 w/ SHOPFALL ($198)
In today’s evolving workplace, the rigid boundaries between formal and casual continue to blur, making adaptable pieces like the J.Crew Lake Shoes invaluable for the modern professional. This business casual ensemble strikes the perfect balance – elevated enough for some client meetings, yet comfortable for those long days at the desk. The key to making boat mocs work in an office setting lies in the supporting cast: the unstructured navy sport coat adds polish without stiffness, while the crisp university stripe oxford and well-tailored khakis create a foundation of classic professionalism. The brown suede belt creates a soft, deliberate connection to the rich leather tones of the mocs, while navy merino dress socks and a navy dial stainless dress watch elevate the look beyond typical casual wear. This approach to business casual acknowledges that comfort and competence aren’t mutually exclusive. In my experience, when you’re comfortable in what you’re wearing, confidence naturally follows. Whether you’re presenting to the team or grabbing a quick lunch with your colleagues, this look communicates both approachability and attention to detail, essential qualities in any collaborative work environment.
J.Crew Heritage Cotton Crewneck Sweater – $49 w/ SHOPFALL ($98)
J.Crew Broken-In OCBD – $68.60 w/ SHOPFALL ($98)
J.Crew Japanese Selvedge Straight Fit Jeans – $124.60 w/ SHOPFALL ($178)
Timex Marlin Hand-Wound 34mm Watch – $259
Will Leather Goods Card Case – $65
J. Crew Texture Cotton Socks – $13.65 w/ SHOPFALL ($19.50)
J. Crew Woven Elasticated Italian Leather Belt – $69.50
J. Crew Lake Shoes – $138.60 w/ SHOPFALL ($198)
Date nights call for that sweet spot between looking effortlessly put-together and trying too hard. The textured green crewneck sweater serves as the sophisticated anchor, elevated by the crisp striped oxford peeking out at the collar and cuffs for a layered, intentional look. Dark, crispy raw denim brings a modern edge while maintaining the refinement needed for an upscale restaurant, and the forest green dress socks add an unexpected pop of personality that shows attention to detail without being flashy. The braided leather belt and brown leather watch strap create subtle textural interest that complements the rich patina of the boat mocs, proving that these casual classics can absolutely hold their own in elevated settings. This look embodies effortless cool because it doesn’t rely on formal pieces to make an impression. Instead, it demonstrates confidence through thoughtful color coordination and quality basics. Whether you’re at a wine bar or a farm-to-table restaurant, this ensemble communicates that you understand the assignment: looking sharp enough to show you care, yet relaxed enough to suggest you’re comfortable in your own skin.
Flint and Tinder Flannel Overshirt – $128
Made in the USA F&T T-Shirt – $38
365 Chino Shorts – $68
Hamilton Mechanical Field watch – $625 (review here)
Flint & Tinder Vintage Leather Belt – $85
“Dang” hat – $40
J. Crew Lake Shoes – $138.60 w/ SHOPFALL ($198)
Weekends are for decompressing and recharging, but that doesn’t mean abandoning all sense of style. This relaxed, yet put together look proves you can be comfortable without looking like you’ve given up on life. You don’t have to live in athleisure! The plaid overshirt in cream, green, and navy creates a laid-back foundation that’s perfectly at home whether you’re brewing coffee on the porch or running weekend errands. Layered over a simple navy tee and paired with tailored chino shorts, the look maintains structure while embracing ease. The brown leather belt grounds the outfit and creates a natural bridge to the brown leather boat mocs, while the mechanical Hamilton watch with its green and brown strap adds a subtle outdoorsy touch that nods to the shoes’ camping heritage. The “Dang” hat is a reminder that your weekend style can (and should!) have a sense of humor. This is the kind of outfit that looks intentional without being overthought, comfortable enough for a movie marathon but pulled-together enough for an impromptu lunch invitation. This is proof that casual doesn’t have to mean careless, and that the best weekend looks can feel good, too.
Smart casual briefcases, classic dive watches, and retro sneakers.
A casual but still put-together look for dressed down winter festivities.
Looking sharp but not over the top. Out on the town or at someone's place.
Tis-the-season to bring some style.
Tues. = Leftovers + extensions moved to the top. 20% off Huckberry's 365 pants, BRF…
Cozy duds, paper pets, some good reads, and a heated outdoor chair.