Whenever I pull together a more conservative outfit, I like to offset it with details that show a little more flair than I would normally employ. I've fallen in love with the cutaway collar on this shirt from Twillory and the functioning sleeve buttons on this Suitsupply blazer. I also decided on a puff fold with my handkerchief to lean less business-casual, and more hashtag-menswear.

Jacket: Suitsupply (similar) | Shirt: Twillory | Pants: J.Crew | Tie: The Tie Bar | Shoes: Zara (similar here) | Handkerchief: Madewell | Watch: Omega (vintage) | Sunglasses: RayBan