What are the most expensive types of dress shoes you own?
I bet I can guess….
They're the ones you NEVER wear.
If you wear a $100 pair once and a $350 pair 350 times – which is the better deal?
$100 per wear? or $1 per wear?
Quality leather can be expensive initially….
BUT if you buy them in the right order you can get the most for your money.
Not to mention – they're one of the first things women notice on men.
So let's say a meteor strikes your house and only demolishes your shoe collection (phew).
What are the 5 shoes you need to buy to rebuild your wardrobe?
Keep reading to find out….
This post was brought to you in collaboration with JL Rocha. I teamed up with Jose Luis again to bring you a one-stop shop for you to find the best dress shoes to rebuild your collection. The designs I helped him with are all classic dress shoe styles that every man should own.
Types Of Dress Shoes 1. Classic Oxford
As far as formal goes no other shoes do the trick better than Oxfords. These are arguably the dressiest shoes with laces you can wear to work. The reason is a closed lacing system, ankle exposure and low-heeled structure. They often come in black or darker conservative brown.
Oxfords are most appropriate with a suit and slacks. You can try a more casual approach with a sports jacket instead. However, you’ll want to be careful selecting trousers. Chinos or jeans usually don't mix well with sleeker-looking footwear.
A couple of features come into play to sort of influence their “formalness.” Some have a cap-toe design while others are on the plain side. Some also include holes (perforations) along the edges.
I personally would go for a black pair of cap-toe Oxfords. This is the best option for formal business wear. It can even do double-duty to accompany your black tie attire (a.k.a. dinner jacket with bow tie) at the grandest occasions. If only one pair can be black, make it this.
Types Of Dress Shoes 2. Wholecut
Minimalistic design is what makes Wholecut shoes attractive. They demonstrate “less is more” in terms of luxury footwear – clean lines and minimal decorative features. Like Oxfords, they’re great for formal gatherings and corporate events.
The relative simplicity stems from their composition. No several pieces of leather have to be sewn together. No extra pieces for quarters and vamps are used. That’s why they feel really sturdy.
Should be they black or brown? I wouldn’t be too picky about this so it’s best to focus on the purpose. Black ones go best with a suit while brown (or tan) ones can match a casual suit.
Either way you want to make sure you’re wearing a jacket with these shoes as much as possible. Wholecuts are a great option for black tie events because the single piece of leather gives it the highest formality. You will want a pair without any decorative broguing.
Types Of Dress Shoes 3. Semi Brogue
This is the type of men’s footwear with those signature perforations. Its history dates back to the 19th century in the farms across Scotland and Ireland. The holes were originally functional – allowing any water from wet surfaces to escape the shoes. Now they’re mainly ornaments.
Almost all brogue shoes have lace panels, low heels, heel caps and toe-caps. The difference between Full and Semi lies in the perforated pattern along the toe-cap edges. Full Brogues (a.k.a. Wingtips) have the holes extending diagonally towards the heels while semi-brogues feature a single neat curve.
What I like about the semi kind is it’s stylish yet not too intricate. Shoes that are fully brogued may look a bit busy. You don’t want a pair that potentially distracts from the rest of your clothes due to an artsy bunch of holes.
I'd recommend a Semi Brogue in tan or a lighter shade of brown. You might want to get one with a contrasting color combo – where the heel, seams and patterns are dark brown. You'll see how it complements a pair of blue jeans perfectly.
Types Of Dress Shoes 4. Double Monk Strap / Penny Loafer
On the formal-casual scale these shoes probably land right in the middle. That counts them among the most versatile types. For Double Monk Straps, we have monks from the earlier years in Europe to thank – who needed an alternative to the sandals they normally used to walk long miles.
Double Monk Strap shoes were designed for security and durability. The dual strap combined with an enclosing buckle provided travelers with extra foot protection. Those are the same features that make them trendy nowadays.
Meanwhile Penny Loafers were the clever brainchild in the 1930s. Their style was an upgrade from the existing loafer through one key feature: a strap across the top that was “split” to resemble a pair of lips. The small opening was useful for stashing any change that kids needed for emergency payphone calls. Today they're perfect for any modern-day stylish man.
Which color is your best bet? It depends – you might want to think more about settings outside the office. These shoes can really be worn in a variety of environments. Find one that goes nicely with the majority of your casual or sporty items.
Also remember this rule about socks: black for a black pair, gray/charcoal for a brown/oxblood pair. Wearing these shoes sans socks is totally fine for laid-back casual occasions. Just ensure there’s a slight break at the end of your trousers.
Types Of Dress Shoes 5. Chelsea Boot / Chukka
Who would’ve known that Chelsea Boots – originally designed by Queen Victoria’s shoemaker J. Sparkes-Hall – were going to be part of the Beatles’ iconic look during their prime? They are now one of the most popular choices for men's fashion.
These ankle-high, close-fitting boots are instantly recognizable. They have a slip-on style that’s similar to loafers. There are also elastic bands on either side of each shoe as well as a loop at the back for pulling. That’s why removing these boots is just as hassle-free as putting them on. Not to mention they’re comfortable and breathable all around.
Chukkas on the other hand are known for their distinct open lacing that consists of 2-3 pairs of eyelets. The name possibly originates from the “chukker” or period of play in a polo match. These boots are also ankle-high with their uppers made of suede or leather. The material for the soles is either rubber or leather.
Either boot type has a unique design and looks good in any available color. Both can do wonders with your favorite jacket or pants. Choose the one you’ll feel most confident wearing wherever you may go (whether it’s at work or trips outside the city).
When trying on a pair of boots: ensure the fit is snug but NOT too tight. The vamp is rather narrow and you wouldn’t want your toes crowding and bulging out. Always wear thinner socks for maximum comfort and avoid thick athletic ones. Finally, your trousers should ideally cover about one-half to three-quarters of an inch starting from the top of each shoe.
General rules apply to all of the above: (1) black is seen as more formal than the others and (2) sleeker is classier.
Each shoe type has its niche and purpose. As an everyday gentleman, you are encouraged to invest in them. Watch your self-confidence grow as you start to walk taller and stand straighter wearing them.