I think adding some style to a casual outfit can be harder than to a dressier one. Throw on a suit, shirt, and some nice shoes and you're already 90% of the way there. But jeans and a t-shirt can fall anywhere from disheveled slob to street style superstar.
The keys to pulling together a great casual outfit are, in my opinion: layers, fit, and shoes. Layers add depth to a look. Adding an unconstructed blazer or a sweater/sweatshirt to a collared shirt elevates a look exponentially. Fit is crucial. Fit may be the most important factor in men’s style. Wearing clothes cut to compliment your body as opposed to accentuate your insecurities makes all the difference. I don’t mean that guys should wear form-fitting clothes, but rather clothes that hang and drape appropriately. Finally, wearing a quality pair of shoes (sneakers, boots, or drivers) makes a strong, personal statement. Well-maintained shoes speak volumes about how you care for everything else in your life.
Below, I’ve pulled together some of my favorite casual clothes and accessories. Just about everything pictured below can be layered with anything else listed to create a great outfit.
Barbour Beaufort Jacket // Bonobos Slim Fit Washed Chinos // Ferragamo Drivers // J. Crew Fair Isle Sweater // Levi’s 501CT Jeans // Tucker Blair Jaws Needlepoint Belt // T. M. Lewin Pinter Mac // Kiel James Patrick Madras Shirt // J. Crew Sweatshirt // Red Wing Oxblood Iron Rangers // Ray-Ban Gingham Wayfarers // Suitsupply Havana Blazer // Charles Tyrwhitt Socks Gift Box // Woolrich Sweater // Nike Sneakers // Twillory White Oxford // Kiel James Patrick Braided Belt // Tucker Blair Wagoneer Card Wallet