5 Essential Shoes and How To wear them

As a man of evolving style you’re probably looking to re-invigorate your shoe rotation. If you've got the standards on lock, it's time to consider your shoe stock and strategy, and it's probably time to branch out. Whether that means picking up a new style or two, or just trying something new with how you wear your old favorites, let's dive in with our go-to five essential pairs and how you should be wearing them. We've got you covered on some no-fail style tips in the expected ways of course, but for something fresh, we've got a few unexpected tips on how to pair them up.

The Captoe Oxford The captoe oxford is about as versatile and essential as a dress shoe gets and they’re defined by their closed lacing, which gives them a smart, elegant appearance. Generally considered slightly less formal than their plain toe brethren, the captoe is an extremely versatile shoe that’s built for days of meetings and polished nighttime vibes.

The Go-To Way To Wear 'Em: Perfect with any type of suit or formal look, the captoe oxford is the epitome of a dress shoe. If you’re wearing a tux, make sure you go with a shiny patent leather.

The Unexpected Way To Wear 'Em: Give your more casual outfits a little bit of polish by dressing down your captoes. Try them with denim and a blazer or even with chinos, a shirt, and a knit tie on Casual Friday.

The Penny Loafer Originally used by Norwegian farmers for comfort and utility, the penny loafer first became popular in the US in the 1930’s and then in the 50’s and 60’s as the calling card for any tried-and-true Ivy League prep. We’ve come a long way from the campuses of the Northeast but the penny loafer is still as stylish as it’s ever been. The key is their mix of casual and dressy, not to mention their easy on/off and comfort. We’re about to enter prime loafer season so make sure you ditch the socks (or roll with no-shows) and give those ankles some air.

The Go-To Way To Wear 'Em: Penny loafers are a natural with denim and chinos, regardless of how formal or casual you go on top, and are ready for week or weekend. Go casual with an oxford or plaid, or dress it up with a knit tie and a blazer.

The Unexpected Way To Wear 'Em: You can dress penny loafers up as they go exceptionally well with a pair of tailored dress pants and a blazer. For a summer wedding or party ditch the lace ups and your socks and try pairing them with a fresh khaki suit to give you that cool (both literally and figuratively) summer suited look.

The Driving Loafer A shoe that emerged during the 60’s and was designed to help rakish Italians handle their performance cars with more ease, the driving loafer was originally made with a longer vamp and soft leather construction which allowed the driver to more easily switch gears. The defining factor of a driving loafer are its soft leather shell and nubbed rubber sole (originally made for grip). The driving loafer similar to the penny loafer in that it’s incredibly versatile and will work well with most outfits. This shoe is all about ease and mobility so when deciding how to style it don’t over think it.

The Go-To Way To Wear 'Em: Toss them on with slim chinos, denim, or even shorts, their comfort and relaxed style will work in most casual situations. Skip the socks though.

The Unexpected Way To Wear 'Em: As with penny loafers, you can ditch the socks and pair them with a more formal chino suit or blazer combo for an event or wedding.

The Double Monk Strap Despite gaining prominence the last few years amongst the style elite and instagram stuntaz, the double monk is actually a classic shoe with a long history of stylishness. Bridging the gap between slip on and dress shoe, the sleek silhouette and bold buckle set up will bring an extra shot of style muscle to everything in your wardrobe.

The Go-To Way To Wear 'Em: Sub in a double monk for your standard dress shoe with your favorite suit look and add some swag to your office rotation. Their sleek profile and subtle details are definitely going to breathe some new life into all your suits.

The Unexpected Way To Wear 'Em: Why leave the style adrenaline just to your suits? Pop your denim up a level and add some polish and edge to your dressier denim looks. Try ‘em with a blazer, a crisp dress shirt, and your favorite dark denim the next time you hit the town.

The Chelsea Boot A favorite among stylish rock stars since they first became popular, the Chelsea boot is one of the sharpest boots a man can own. The sleek, tapered profile blurs the line between boot and dress shoe, making it easy to dress up or down. If you’re ready to elevate your shoe game up to, well, rock-star status, the Chelsea boot is your move. Pro tip: Make sure to keep the leg and hem on your pants nice and tapered.

The Go-To Way To Wear 'Em: Given its heritage, denim is obviously a natural fit with the Chelsea boot. Don’t be afraid to dress it up too, this one doesn’t have to just be casual.

The Unexpected Way To Wear 'Em: If you’re truly ready for a next-level move, rock your chelsea boots with a slim suit and swap the dress shirt for a slim-fitting t-shirt. This look has night out written all over it.