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Fall & Winter Custom Footwear: The Best of the Season for Men

Posted Sep 6th, 2022 in All News, Fundamental Style, FW 2022, Personal Style, Style Knowledge, Winter & Fall

As we transition into the fall and winter seasons, it's the perfect time to start thinking about custom footwear. King & Bay specializes in offering a bespoke approach to men's shoes, featuring endless customization. 

Fall & Winter Footwear: What Men Should Be Wearing This Season, King & Bay Custom Clothing, Toronto, Canada

It's Important for Men to Look Good from Head to Toe

Some might argue that you can tell a lot about a man by the shoes he wears. One thing is for certain - paying attention to your shoes will certainly let people know you have an eye for details. We have always believed that it's the details that count and we offer beautifully crafted custom footwear that will suit your personal style. There's really no better way to complement your custom King & Bay garments this fall and winter than with the perfect custom shoes. You can learn more about our custom footwear here.

Our Favourite Fall & Winter Footwear for Men

Chukka Boots

Chukka boots are a closet staple for men because they are comfortable, stylish, and durable. They are traditionally an ankle-high boot in leather or suede. Pairing them with jeans is one of the most versatile combinations and chukkas help elevate this simple, casual look. For smart casual looks, any style of chukka could work as long as the outfit is balanced. And for more formal situations, your jeans should be darker and the chukkas should be pointier at the toe.


The hallmark of the monkstrap shoe is that it is fastened by a buckle which replaces traditional laces and eyelets making it a practical shoe since it can be easily slipped on. Monkstraps are classy and fashionable shoes. You'll want to wear this type of footwear with pants that have a more tapered leg opening or you run the risk of wide leg pants getting caught on the buckles which will create a sloppy look. The best sartorial accompaniment to the monkstrap is a well-tailored suit and King & Bay has you covered for both custom footwear and custom suits.

Chelsea Boots

Chelsea boots are similar to Chukkas only they are a laceless ankle-high slip on with either an elasticized or zippered side opening. They have a timeless shape and design and are versatile so men can wear them casually with jeans or formally with a suit. Leather Chelsea boots are considered more formal that the suede option.


Oxfords are as versatile as they are timeless, and they are perfect for looks ranging from formal to smart casual. We think they are an essential staple for men, regardless of their style. Brown leather oxfords are the perfect shoe to wear with dark brown, grey, or navy suits. Tan oxfords are a great choice for less formal looks and can be worn with tailored navy pants, denim trousers, or bright-coloured chinos. And finally, black oxfords are a must for every man's closet. You can style them with almost every colour for a conservative, polished look. We think custom oxford shoes are a great investment for stylish men in the fall, winter, and all year.

Our Fall Winter 2022 Collection will feature custom shoes mentioned here and men will want to get their hands on them (or feet in them). Footwear should always be an important consideration because the proper pair helps to complete an overall look.