Shoes can make or break an outfit, but there’s no right or wrong way. It’s possibly the biggest variable to consider, as most guys don’t have a hundred pairs hanging around and need their kicks to do double duty (at least). 

It used to be that a gentleman started with three pairs of shoes: First is a nice, clean oxford in black - goes with everything and adds to everything with understated confidence. Next is a Derby shoe in brown, adding a little looser style to the business at hand. And the third is a brogue - style with character and perfect with blazers and casual suits.

That’s not a bad way to go and it’s a great way to begin thinking about footwear, but the truth is that times have changed and men’s fashion has lost much of its rule following conformity and developed further into individualized style. 

Which can make things a bit confusing when choosing the right pair to lead your steps.

Shoes can either dress up or down depending on what style you choose and what the day’s plans have in store. More and more, we need to fit in a lot of different things in a day and versatility is a must. 

Sandals have become more than just sandals. Sneakers can add pop to a drab outfit or tone down something more formal while remaining comfortable all day. 

Leather shoes and boots can dress up something casual or (especially these days) add elements and texture that have their own charisma. 

First, there’s sandals - those minimal flaps that mark the leisure hours. It’s maybe not surprising that Japanese designers visvim and Suicoke have come up with a perfected performance sandal, somewhere between a sandal and a sneaker, that can somehow still look good with socks and travel further distances than from your car to the beach. And at the other end, Hender Scheme’s leather slipper has more in common with a loafer than with flip-flops.

Sneakers just hit their centennial mark and have held a place in fashion ever since. Comfortable and often colorful, they can can mix and balance out other colors and tones you’re wearing or be the centerpiece of the whole deal. Shoes Like Pottery make a better version of those original canvas sneakers in all the classic colorways.

Performance has its own aesthetic and sporting men have been confidently wearing what works best for their long days and long strides without needing any permission to appreciate what a good sneaker can do. 

And when a brand like Brandblack starts with pure performance design and allows for color and graphic to step forward, the shoes have real punch - but you’d expect nothing less from the designer behind FILA’s Grant Hill II.

Sneakers have become both the new workboot and the colorful beginning and end to an outfit.

Brands like Diemme and Buttero have recognized the workhorse aesthetic of boots with the streetwear panache of sneakers for shoes that do both equally well. And going all the way to connect sneakers with a refined outfit, Engineered Garments and Harmony have done collaborations with New Balance and Puma respectively to blend right into the season and shine the light on why classic sneakers have lasting power when mixed with the right gear. 

Sneakers are streetwear through and through - even when worn by distracted dads. 

Of course, sneakers aren’t the only streetwear favorites out there. Loud patterns up top sometimes demand clean leather on your feet. Maybe Timberlands were intended for lumberjacks, but hip hop kings - coast to coast - have been turning Timbs into slip-ons since the 90’s. And let’s not forget what Wu-Tang did for Clark’s Wallabees

Existing in the hard-to-define middle ground between sneakers and quality leather shoes, Hender Scheme comes up again with their MIP interpretations of classic sneakers in vegetable-tanned leather. Imagine having your favorite sneakers built to last as long as a pair of boots and become a patinaed signature of personal glory. 

Finally, we come to leather dress shoes and boots. A good pair of leather boots is something that every man understands, but there are answers to leather footwear that have a lot more going on than just walking and working.

Though versatility is the name of the game, it’s not the only combination to celebrate. Brands like visvim, Yuketen, and FEIT combine historical elements and craftsmanship to surprising effect with designs that have one foot in the past and one in the future and ready for town or trail.

Footwear is too often overlooked in men’s style, which is surprising considering the conventional wisdom that “if you take care of your feet, you may actually get where you’re trying to go…”