The 10 Best Men’s Outfits for a Work Happy Hour in 2027

Wear the Stevens Sportcoat over a plain white tee, as the maker’s model does, or a knit, with chinos or dark denim. It is 6-oz. 100% linen puppytooth with a 2.5" notch lapel and half body lining, and it is dry clean only. It is listed at $278.60, down from $398.00.

Ministry of Supply says the Kinetic Blazer is 100% Solotex or Primeflex warp-knit polyester, unlined, wrinkle resistant and machine washable. Wear it over a button shirt, as the maker’s model does, and go straight from the desk to the bar. It costs $398.00.

Todd Snyder makes this sweater entirely from merino, with a quarter-zip mockneck, a tubular placket that hides the zipper and a saddle shoulder. It reads smart on its own and needs no jacket. It costs $278.00.

The Duke is a Chelsea boot in Chocolate WeatherSafe Suede with a Goodyear welt, a Poron antimicrobial insole and a fully lined glove leather interior. Wear it with chinos or dark denim and a jacket or a knit. It costs $199.00.

Everlane says this ribbed collared sweater is 100% extrafine merino wool with a soft feel and substantial weight, and the collar brings polish. Pull it on with jeans for dinner or wear it with trousers. It costs $198.00.

The Marine Layer Coastal Merino Sweater Polo is 100% extrafine merino wool knit with donegal yarn for flecks of color. It can be machine washed cold on delicate and laid flat to dry. It costs $178.00.

Bluffworks says the Ascender chino wicks moisture, repels water and resists wrinkles and odors, with a secret stretch waistband. Wear it with the sportcoat or a knit. It costs $138.00.

Taylor Stitch’s Democratic Jean is 14-oz. organic cotton indigo selvedge denim with a button fly and selvage detailing on the coin pocket. Keep it dark and unfaded, and wear it with a knit or a sportcoat. It costs $178.00.

The Lincoln Penny Loafer is Coastline Oil Snuff Suede with a hand-stitched moccasin toe, Blake stitch construction and a lightweight EVA outsole. It suits a warm evening with chinos. It costs $188.00.

The Outerknown Blanket Shirt is 100% organic cotton BlanketWeave twill with an easy fit and chest pockets with button flap closures. The maker says it buttons up for a boardroom meeting or dinner the same night. It costs $168.00.