Read on to learn which shoes never go out of style for men’s wardrobes.

A Guide To Timeless Men’s Footwear

Nothing can ruin an outfit quicker than the wrong pair of shoes. However, this simple addition can elevate your style to another level if done correctly. In comparison, done wrong, your outfit loses all effectiveness and can look disjointed as a completed look. 

Like clothes in our wardrobe, some footwear has cemented themselves as timeless classics every man should own. So whether it’s boat shoes NZ for summer, or stylish winter boots, stocking your closest with these staples means you will never be short of options.

Timeless Style: Mens Shoes That Will Always Have A Place In Fashion


Oxfords are easily the most classic men’s shoes available. Commonly worn as a dress shoe for the office or formal occasions, these staples have a long history and reputation to match. In addition, they come in a variety of neutral tones and minimal detailing, making them incredibly versatile within your wardrobe. 

They are known for smooth uppers, a low heel, and closed lacing, giving them an incredibly sleek look, ideal for a sharp suit or tuxedo. You can never go wrong with a pair of leather oxford shoes. 


To the unfamiliar eye, brogues and oxfords might look somewhat similar. But in fact, they are pretty different from each other and serve two different purposes. Originally designed to wear out in the countryside or any wet landscape, these shoes are designed with small holes along the top, meant to allow water to drain out of them. Noways, these serve more as a style feature. 

Although they are not considered as formal as oxford shoes, brogues are still a very smart footwear option. They are appropriate for most formal settings and the office—the perfect addition to the modern man’s wardrobe. 


Originally designed as a house slipper for King George VI, loafers have come a long way to cement themselves as one of the most versatile footwear options available. Thanks to their sleek, laceless design, loafers can be worn all year round to many different social events. 

Timeless Style: Mens Shoes That Will Always Have A Place In Fashion

Traditionally made in leather, faux leather, or suede, they can be paired with shorts, fitted jeans, and suits, effortlessly taking you from day to night. However, in more formal settings like weddings, it might be best to leave them at home if you are unsure about the dress code. 

Chelsea Boots

After first being designed during the 1800s and regaining popularity in the 1960s, the Chelsea boot is a stylish and sleek boot option for winter. Well-known for their pull-on design and elasticated panels, they are ideal for taking long walks and wearing them for a night out with friends. 

Purchasing a pair of leather Chelsea boots grants you the option of an additional formal winter shoe to choose from for any semi-formal occasion. Get a pair in black, dark gray, or dark brown to have the maximum opportunities to mix and match with your clothes.

Timeless Style: Mens Shoes That Will Always Have A Place In Fashion


A pair of fashionable sneakers is a must-have for any man for the perfect combination of style and comfort. They can be worn throughout the year and take minimal effort to style if done correctly. These aren’t your dad’s sneakers anymore, thanks to the heavy influence of street style. 

They are best paired with shorts, joggers, and fitted jeans. Of course, If you feel daring and ready to push the envelope, you can pair them with a suit. But this style has yet to be entirely accepted and is often frowned upon in situations that require such formalwear. 

Boat Shoes

Boat shoes are the ideal summer shoe option for men. It is worn best when you aren’t trying to dress it up too much. The perfect pairing for it would be shorts, but here you can opt for cotton, linen, or denim, depending on how ‘formal’ you would like your look.

If you want to pair them with long pants, ensure they are cuffed or end at your ankle. Bootleg pants or pants that cover the top of your shoe will look out of place with this footwear style. 

Monk Strap

Monk strap shoes are relatively unique in their design compared to the traditional oxford. Instead of laces, they have straps, which are secured by either a single or double buckle, giving them resemblance to shoes traditionally worn by monks. 
They are considered an unusual but equally elegant alternative to the standard lace variation, with a sleek and minimal appearance. They are deemed smart enough for formal events but will still maintain enough versatility to be worn causally.

Timeless Style: Mens Shoes That Will Always Have A Place In Fashion

Desert Boots

It is always a good idea to have an alternative option for winter that is more rugged for harsher conditions. What better choice than the desert boot, which has a long sports and military culture history. 

While they are available in multiple styles, the proper desert boot has two or three eyelets, and a rounded-toe box, with the top of the shoe hitting the ankle. The ideal shoe variation would be a suede option (preferably treated with a water-repelling solution) and leather soles, which will last longer than the slightly more comfortable alternative, crepe sole.


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