Dressing casually is no excuse to dress lazily. When you decide to dress down (perhaps on weekends or a day off), its important to give thought to the fabric and details of what you’re wearing.
My advice: invest in quality basic pieces. Staple items are crucial to have in your wardrobe, as they're easiest to build off of. One item that I suggest you invest in is handcrafted dark denim. Find yourself a durable pair without any of those gaudy embellishments on the rear pockets. A nice pair of jeans will last you years if properly cared for, and they're versatile enough to be worn with a blazer for when you need to spruce things up. One particular brand I've worked with that has continued to impress me is Mott & Bow. They manufacture some of the highest quality denim at a very affordable price (right around $100/pair). I often tend to wear mine with a classic OCDB or polo shirt. Austin, TX-based Criquet Shirts makes one example, the Player's Shirt, that I particularly like. It features removable stays for a more rigid collar- as the dreaded "bacon collar" is never a good look. In the images below, I'll show you simple ways to dress up your pair of dark jeans.
I'd also recommend investing in a shawl-collared cardigan. The beauty of this piece is that it will elevate any look. Personally, I love how the shawl can still be visibly seen when layered underneath an unstructured jacket. During the colder winter months (or fall and spring too, if you're a New Yorker like me), you'll catch me sporting one of these most days of the week. This item can be found everywhere- with knitted examples available throughout the year from Uniqlo, J. Crew or Jack Threads. Here's two more ways in which I style my shawl-collars:
Now, you just can't go wrong with a sturdy brown pair of dress shoes with replaceable soles. Similar to my other recommendations, these are also very simple to dress up or down. Lace them up for a quick walk down to Whole Foods or pair them with a suit for your 9 to 5. With regular maintenance, a good pair can last you a lifetime. This particular pair is from the Australian company Bared Footwear.
Finally, my last recommendation would be for a timeless dress watch. In my opinion, this is the only piece of jewelry that a guy truly needs. Forget the gold bracelets, hubcap-sized watches, and pinky rings- It’s important to simplify your look, as over-accessorizing tends to give off the atmosphere that you're also over-compensating. Two stellar watch companies that I’ve worked with are Daniel Wellington and Shore Projects. I prefer to wear my Shore Projects timepiece more casually and the Daniel Wellington more formally, but this will also depend largely on which watchband you choose to pair it with.
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