Choosing the right shoes can be daunting.
Nobody wants to worry about their shoes ruining their outfit.
So I found out which shoes men are buying again and again.
Today I'm going to share what I learned with you…
There's wisdom in crowds guys,
So let's look at the 5 dress shoes that just keep flying off the shelves.
Best Men's Dress Shoe #1 – Cap Toe Oxford
- Closed lacing system: the quarters (back leather part) are sewn underneath the vamps; both regions stay close together and this creates a smooth silhouette
- Each shoe has a thin line that marks the toe area (hence the term “cap toe”) and another that goes from the heel to the lacing flaps
- No broguing or intricate details
Wearing Cap Toe Oxfords
These classic dress shoes are popular for their sleek, elegant appearance. You can easily wear black cap toe oxfords with formal wear or strict business attire. If you're thinking to go more casual, they can also work with casual suits and odd trousers.
If not black – I suggest choosing shoe colors like oxblood or medium/dark browns. You'll want them to help you dress sharp as opposed to flashy. Darker shades tend to be more formal and sharp-looking than lighter ones.
Best Men's Dress Shoe #2 – Wholecut
The wholecut dress shoe is seen as more modern and fashion-forward. But I think in about 20 years…it'll probably turn into a classic as long as men keep buying them.
- The upper (all leather material above the sole) is made from a single large piece of unblemished leather; stitching is only done at the back
- The shoes have a clean, smooth construction and narrow shape
- No lines, broguing or intricate details
- The leather is carefully selected which increases the shoe price
Wearing Wholecut Dress Shoes
There's a “less is more” rule when it comes to formal dress shoes. That makes the minimalist design of wholecuts a great match for a nice black suit or tuxedo. Wear black wholecuts if you're attending a fancy dinner party. You can also try wearing dark brown to the office or laid-back social settings.
Best Men's Dress Shoe #3 – Semi-Brogue
This one has the trademark perforations known as broguing. Brogues have come a long way from their inception in Scotland centuries ago (first made with actual holes to drain out bog water). These shoes are now used for fashion…with semi-brogues still pretty high on demand.
- Broguing along the toe caps, vamps, and at the rear end of the shoes
- No additional broguing at the front; simpler in design than full brogues/wingtips
Wearing Semi-Brogue Dress Shoes
Broguing makes any dress shoe more casual. So you wouldn't wear semi-brogues to a black tie event or a formal occasion. You also shouldn't partner them with a business suit (unless they're black ones) in most cases.
Instead, try getting a medium or dark brown pair to match with your chinos or denim jeans. Semi-brogues are also a great way to spruce up a casual suit of any color besides black. As long as you're in a casual environment – they'll come in handy.
Best Men's Dress Shoe #4 – Classic Penny Loafer
It's really no surprise that many guys love penny loafers.
They're comfortable, easy to slip on and off, and also super convenient to travel with. I'd even say they're one of the most versatile men's dress shoes out there.
- Non-traditional dress shoes; made without shoelaces or eyelets
- Each shoe has a horizontal band with a triangular hole (originally designed for schoolchildren to store change for taking the bus after class)
- The slipper-like silhouette means you can wear the shoes sockless or with low-cut ankle socks
Wearing Classic Penny Loafers
Since penny loafers and all other loafers are laceless, they're not historically known as “high-level” footwear. Don't use them for a wedding or business meeting with important clients. But if you'll be just hanging by your office desk all day – they're totally fine. But do bring along a pair of black cap toe oxfords as a backup.
You can pick any color for these dress shoes. Dark browns or suede might be your best bet if you're going to wear dark shorts or denim jeans. But feel free to experiment with different casual ensembles (gray jackets, button-down shirts, odd trousers, chinos, etc.) to see what looks best.
Best Men's Dress Shoe #5 – Chukka Boot
Then we have the chukka, which is definitely one of the most comfortable and stylish men's boots available.
The chukka is low-ankled and designed with only a few eyelets. Its style evolved from the deserts boots used by the British army back in the WWII era.
Chukkas are a nice change from your typical dress shoes. With the extra covering – they can allow you stand out a little more than other well-dressed guys in the crowd.
- Open lacing system: the quarters go over the vamps instead of underneath them; this spreads out the lacing flaps some more
- Soft calfskin or suede is more commonly used for the upper, while crepe rubber is often used for the sole (especially boots with 4 or more eyelets)
Wearing Chukka Boots
Open-laced shoes are generally more casual than closed-laced. That means you're better off saving your chukkas for social settings (where you come in a casual suit and odd trousers or jeans). But remember that 2 eyelets make the boots slightly more formal than 4 eyelets.
If you want dressier chukkas, keep the number of eyelets to 2 and make sure they're made from a smooth, high-end leather material. It should be leather that can be shined easily and looks good over time. The most elegant chukkas also have a Blake-stitching construction. But only get the best kind that you can afford.
Buying Men's Dress Shoes: Leather or Rubber Soles?
Is this a crucial decision? Yes. The long-term differences between leather and rubber soles are quite big for dress shoes.
If your goal is quality, durability, and elegance…you'll be leaning toward leather soles. They're not going to break down all of a sudden and need replacing. There are some soles which comprise multiple layers of leather – and triple-leather soles will outlast any rubber sole. The downside is they may not be as comfortable as rubber soles. They're also at risk of looking worn out if the leather hasn't been done correctly.
But let's say you commute to work every day. Maybe you need shoes that can handle rough pavements or unexpected weather changes. That's when rubber soles are ideal. They do have a “clunky” appearance and shorter lifespan, but rubber does have more traction and shock absorption than leather. Your feet would appreciate that in the long run.
A better solution? Buy shoes with leather soles and have a cobbler add a strip of rubber below. This is actually a great compromise – you'll take home a nice pair of dress shoes while still getting the necessary traction for all that walking.