17th-18th November 2018 - Old Truman Brewery

The dress shoes every gentleman should own

Published on 29th June 2018


Guest Blog by Undandy 


You can’t make a first impression twice. With your shoes as the sartorial window to your soul, it’s important to consider what they say about you. Recent research showed that strangers could accurately predict a person’s age and salary based on their style of shoe. To get the inside pro’s opinon on what are the classic dress shoes every gentleman should know and own, we spoke to footwear experts Undandy, the custom, handcrafted dress shoe. The brand is direct to customer, offering clients the ability to design their very own shoes as well as offering made to order shoes. Each pair of shoes are handcrafted in Portugal and as Undandy are direct to customer, there’s no middle man involved and therefore no mark up on your shoes.


So according to the cobblers and style aficionados at Undandy, here are the classic men’s dress shoes that every discerning gentleman should have in his wardrobe:-


The Oxford

The style is perhaps the most classic of all men’s dress shoes and has a deserved place as a wardrobe staple. The Oxford is usually considered a more formal shoe and works well for occasions like work, weddings and job interviews. The characteristics of the modern-day Oxford are in its specific method of construction with a closed lacing system, exposed ankle and low heel. Although one can play around with textures and leathers, it is wise to keep your Oxfords sophisticatedly stylish in traditional hues such as brown and black.

The Derby

The ultimate all-rounder, the Derby is known for its casual, comfortable style – an appropriate dress shoe for every day. The main difference for the discerning gent between the Oxford and Derby is the seam of the vamp that is made under the quarters, creating an open-faced lacing system. This subtle detail gives the Derby the extra edge in being a slightly more informal style.

The Monk Strap

The origin of the monk strap dates back to the 15th century, worn by European monks who embraced the style for inherently practical reasons, as a closed toe version of the traditional monk sandal. Despite the shoe’s humble origin, the style has since evolved to become an integral part of any discerning modern gentleman’s wardrobe and can be worn from the boardroom to bar with effortless ease.



The Boot

Another smart casual style that deserves a place in your wardrobe. A dress boot such as a chukka boot is an unexpected but refreshing pairing for work and weekend wardrobes and extremely versatile to incorporate into an everyday look. The name “chukka” is thought to come from the game polo, where “chukker” is a period of play.


The Loafer

Although more commonly associated with the iconic preppy style of Ivy Leaguers, the loafer began as a shoe worn by Norwegian fisherman in the 1800s. The not so humble slip-on is perfect casual option for warmer months and when you want to elevate your usual style uniform.


So, what’s the scorecard? How many of the classic dress shoes do you own? And the good news if you’re missing some of the key styles from your wardrobe with Undandy you can actually customise your very own shoes and you’re totally in control of the details. So, if you’re after that seemingly impossible pair of shoes to finish off an outfit hanging in your wardrobe, the solution is easy. Simply design your own.



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