Michael has been an online writer for more than 6 years. His interests include video games, technology, and men's fashion.
1. Low-Top Sneakers
Sneakers are the most common type of shoe for men. Try to look for sneakers that are classic and simple. Any sneaker with more than 2 colours is a no-no, unless you are looking for a sport shoe. Low-tops are great for a casual look, such as college.
Look for good quality brands; durable sneakers are what you're after. These are the shoes you will be spending most of your week in. Vans, Chuck Taylors, Jack Purcells and Keds are the easiest to find, but less common brands like SeaVees, Spring Court, Superga, PF Flyers, Tretorn and Feiyue are worth hunting down if you want something more unique.
2. Desert Boots/Chukkas
Chukkas seem to look good in anything. They're more dressed-up than a sneaker but not quite as proper as dress shoes—which is why they are the go-to shoes for anything in between. They're not too pretentious, yet they look sharp enough to impress the date. Beeswax leather and taupe or sand suede are the most versatile choices.
The price point for chukkas seems to vary, but some great brands include Kohls, Red Wing, Sperry and Cole Haan, along with classics like the Clarks Desert Boots.
Loafers are a great look that's best suited for spring/summer. They're best worn with low-cut pants or shorts. You can get more formal-looking loafers with leather, but I think they work best in casual attire. Loafers look great without socks.
Rancourt and Oak Street make mid-range models, and shell cordovan Alden Leisure Handsewns are the holy grail. The types include full-strap, pinch-penny, beefroll, tassel and venetian loafers.
4. Boat Shoes
These are on the same boat as loafers: Boat shoes can be worn on the same occasions as loafers, and they also look great without socks. I remember a mate telling me boat shoes would never be fashionable back in 2011, and look how far we've come! Hate to say I told you so, Aaron!
Wear Sperry Top-sider A/Os in Sahara without socks and you'll be set for the day. If you want to go higher-end, Sperry has done some designer collaborations (Band of Outsiders, recently), and shoemakers like Alden, Allen Edmonds, Quoddy and Russell Moccasin all make boat shoes.
These are a fashionable alternative to flip-flops/sandals. They're incredibly casual and perfect for the warm summer beaches. Try espadrilles on those summer days when you don't feel like wearing boat shoes.
Some notable brands include Toms, Soludos, RopeySoles and Drilleys.
6. Oxfords and Derbies
No matter what season of the year it is, you'll probably need some more traditional shoes for formal events. You can't go wrong with a pair of brown/black leather oxfords or derbies. Try to steer clear from some of the lighter colours unless you know what you are doing. Avoid square toes and any cheap, shiny leather.
Benjamin G from Australia on April 24, 2015:
Great article. My favourites are comfortable boat shoes, but in winter I like to switch to Chelsea Boots.