Business Casual Outfits That Easily Transition From Day To Night | Advice From Our Stylists

Business Casual Outfits That Easily Transition From Day To Night

The way you dress for work, whether it is business attire or business casual attire, life is easier if you have things to wear that transition from office to night on the town. Many men’s outfits look at home in one and not the other. To help we have put together a guide for what to wear to smoothly go from office to happy hour and beyond.

The featured image is a man on the street wearing the Heath Cap Toe Oxford in Cognac.

Shelton

As the temps drop, try a pair of fitted, checkered pants and a rust colored sweater for a warm business/casual look. Our Shelton Medallion Toe Oxford has a sleek profile and enough design details to balance and compliment the strong pattern of the pants. Together they form an unbeatable combination for office or after hours.

Shelton Medallion Toe Oxford in Tan. Shelton Medallion Toe Oxford
The featured image is a man on the street wearing the Heath Cap Toe Oxford in Cognac.
The featured image is a man walking down the street in white jeans while wearing the Kingston Plain Toe Chukka Boot.

Wexford

Jeans with a crew neck sweater is a classic look that never goes out of style. Take that classic look with to new heights with a pair of colored jeans in a modern fit and a boot like our Wexford Cap Toe Chukka Boot. The unstructured styling of the boot provides the perfect finishing touch.

Wexford Cap Toe Chukka Boot in Tobacco. Wexford Cap Toe Chukka Boot
The featured image is a man walking down the street in white jeans while wearing the Kingston Plain Toe Chukka Boot.
The featured image is a model wearing the Sutcliff Plain Toe Monk Strap in Black Multi whilc sitting on a bench.

Madison

Wearing all black is a timeless classic. Elegant and sophisticated, it’s great for the office and a night out. As casual looks go, you can’t go wrong with a black jacket, black jeans, and black shoes. But to turn it into something really special we suggest getting a little wild with our Madison Plain Toe Boot. Its croco print leather detail adds a pop of color and flair without being too flashy to really take your look to the next level.

Madison Plain Toe Boot in Gray. Madison Plain Toe Boot
The featured image is a model wearing the Sutcliff Plain Toe Monk Strap in Black Multi whilc sitting on a bench.
The featured image is a model looking off into the distance while wearing the Donovan Moc Toe Drop Tassel in Cranberry.

Pomeroy

Looking for the perfect shoe to complement a classic look like a white oxford shirt, cuffed black chinos, and no-show socks? To really show off this cool black and white look it needs a focal point. Give it the right contrast with a loafer like our Pomeroy Moc Toe Bit Slip On. The color, texture, and its casual yet dress styling adds an interesting design element to the two-tone look.

Pomeroy Moc Toe Bit Slip On in Cognac. Pomeroy Moc Toe Bit Slip On
The featured image is a model looking off into the distance while wearing the Donovan Moc Toe Drop Tassel in Cranberry.
The featured image is a man sitting on concrete steps wearing the Maguire Wingtip Oxford in Brown.

Kitt

Put on a fitted pair of pants with a floral pattern short sleeve shirt, and just like that you have the perfect warm weather casual look. But the right shoes will really make this look pop. Nothing does this better than a modern wingtip oxford like our Kitt with its unique weave-like design on the vamp.

Kitt Wingtip Oxford in Brown Multi. Kitt Wingtip Oxford
The featured image is a man sitting on concrete steps wearing the Maguire Wingtip Oxford in Brown.
The featured image is man leaning against a car and wearing the Baldwin Moc Toe Double Monk Strap.

Farwell

Finding the right shoes to wear with a t-shirt and jeans outfit is the key to giving this look your own touch of personal style. A sharp pair of double monk strap shoes like our Farwell Wingtip Double Monk Strap is sure to elevate the look. It also has the added bonus of being a versatile style that looks just as good with a suit as it does with jeans.

Farwell Wingtip Double Monk Strap in Burgundy. Farwell Wingtip Double Monk Strap
The featured image is man leaning against a car and wearing the Baldwin Moc Toe Double Monk Strap.
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