The Chelsea boot epitomizes the contrast of casual and formal. They’re a great way to update your look because they’re a cross between boots and dress shoes.
2. The Dress Sneaker
Everyone needs a pair of sneakers that have a casual vibe but still maintain a clean sense of style.
A simple pair of sneakers will go with almost any outfit. Choose one of our top picks and pair it with jeans, shorts, chinos, or even parachute pants. Perhaps not parachute pants. But everything else is up for grabs.
3. The Trainer
Sometimes you just need a shoe that you can slip on and go. This is the type of shoe you wear to get you through the tough days.
Of course, you don’t have to limit these sneakers to running errands; paired with joggers, they can also serve as the foundation of an amazing laid-back casual Saturday outfit.
While the term “trainers” can technically refer to any type of running or exercise shoe, we’ll stick to the fashion side of things. Sports footwear is a whole different ballgame, and we’re not going to get into that here.
4. The Chukka Boot
Chukka boots are simple in design and can range from ultra-casual to dressy and formal.
Take a quick inventory of what your wardrobe requires before deciding on a chukka.
If you work in a more formal, sleek chukka, a more formal, sleek chukka is your best bet.
If comfort is more important than formality and structure, a desert-campaign-style WWII-era boot like the Clarks Desert Boot or the Crown Northampton Desert Boot is more appropriate.
5. The Loafer
Loafers are the adult equivalent of slip-on shoes.
They’re a good mix of high-end style and a low-key desire to have fun.
The kingpin shoe of the 1950s is now the newest addition to your walk-in closet.