You’re on a first date. Dressed to impress. Trousers are pressed, the shirt is ironed, and the details are on point!
She arrives grinning from ear to ear. And then looks down and sees them… Your cracked, 10-year-old, square-toed leather shoes.
Dress shoes can make or break your outfit, gentlemen. They’re arguably the most important investment a man can make in his closet. Luckily, you only need 5 pairs of dress shoes to upgrade your shoe game.
#1 – The Black Leather Oxford
The first shoe you should start with?
Black Leather Oxfords.
The sleek simplicity makes the Oxford the perfect choice for formal occasions.
A pair of formal black oxfords will carry you through the most formal of events – black tie, weddings, funerals and job interviews.
The difference between an Oxford and a Derby is the closed lacing system – the bottom of an Oxford shoe’s lacing section is sewn closed.
The shoes should be made of box calf leather and it should not have any broguing. Oxfords are the best worn with business suits and professional attire, but not suitable for casual occasions with jeans or khakis.
Keep in mind that the Oxford is a dress shoe – purchase a pair with leather soles and be sure to shine your Oxfords thoroughly to prevent them from dulling.
Whether you are wearing a tux to a black-tie event or a business suit, these minimal shoes will complement and add a dose of formality to your attire.
#2 Brogue – The Brown Leather Brogue
A footwear staple for the contemporary gent.
Originating in the marshy bogs of Scotland, brogues were initially designed with real holes to drain out water. The traditional perforations on the shoes upper – the brogueing – gives the shoe a distinctive character that other smart shoe styles lack.
What’s so unique about the brogue is its versatility.
A shade of light brown can be limiting because it tends to look strange with dark suits. A medium to dark brown pair can look great with any suit color except black and will still work with chinos or jeans
Although a brown wingtip brogue is ideal, leather brogues in tan, chestnut or chocolate all work seamlessly with your wardrobe, allowing you to create the maximum number of outfit combinations.
Traditionally, brogues are less formal than oxfords. Consider them for work, especially if you work in a laid-back office. These shoes are suitable for outfits ranging from smart to smart-casual. Full brogues can be worn with outfits ranging/ from the formality of a three-piece suit to a casual pair of jeans.
For a smart casual and comfortable, yet refined look, wear them with a white button-down shirt and rolled-up dark denim jeans.
#3 – Slip On (Loafer Or Monk) – The Suede Loafer
Moving down the formality scale, a loafer is a slightly more casual shoe. The laceless silhouette features an elegant design that makes the loafer a highly versatile style, right after a leather brogue.
The slip-on loafer was originally designed as a house shoe for King George VI. Loafers offer the ideal silhouette for going sockless, making them the choice of footwear in warm weather locations.
Penny loafers are the most popular choice although if you were stranded on a stylish European island with just one pair of shoes to wear every day, a pair of brown double monk straps would be an excellent choice!
The comfort of these shoes is best matched with smart and smart-casual ensembles. Dress up or down a loafer with a light-weight linen suit or a button-down shirt and chinos.
#4 The Leather Lace-Up / Slip-On Boot
If you have already secured yourself a quality pair of oxfords, brogues and loafers, the next pair of shoes in line to complete your shoe selection is a pair of leather dress boots.
Smart leather boots are rugged and dressy, making them a versatile choice to complement just about any look. Your options range from semi-casual lace-up boots to dressier slip-on Chelsea boots.
- Leather Brogue Boots: This is a boot that works with suit trousers as well as with jeans. Wear them for a dressier take on rugged.
- Lace-up leather boots: Crepe-soled desert boots are a popular option but they add a casual touch to your outfit.
- Chelsea boots: The Chelsea is a slip-on style, like the loafer, with an elastic ankle that makes them flexible and comfortable. These are the perfect boots for a day at the office that extends into a night out on the town.
Leather boots can be teamed up equally well with tailored jackets during the work week as with a pair of jeans and a T-shirt at the weekend.
A pair of rugged leather lace-up boots, ideally with rubber soles will keep you sure-footed in rough weather.
#5 Wholecut Leather Shoes
This one’s a wildcard. They are not a required item in your shoe wardrobe in terms of functionality, but in terms of elevating your style.
Wholecut leather shoes exude pure elegance through a minimalist, narrow shape, with clean lines and a smooth surface.
The upper (the leather that is visible above the sole when a shoe is worn) of a wholecut leather shoe is constructed from a single piece of leather. Wholecuts are made using a flawless piece of skin, ensuring high-quality leather. A great deal of expertise and skill goes into making a pair of wholecut shoes, a fact that is reflected in the relatively high cost of these shoes.
Probably the dressiest shoe you will own, these versatile high-quality leather dress shoe can accompany you through your entire day.
Wear them from the office to a dressier evening event or pair them with a pair of smart jeans.