Dress shoes for men are a minefield. Everyone is giving advice, and much of it will lead to you looking like you just showed up to prom… in 1998. I’m going to list a whole bunch of shoe options for you below because I think it’s important for you to know what’s out there. But to make it easy, follow this check list:
Dress Shoes I Need to Own:
- 1x Cap Toe Balmoral
- 1x Dress Loafer (Your Choice)
- 2x Cedar Shoe Tree
Dress shoes are one of those areas where it makes sense to invest in quality.
A good quality shoe can be re-soled and, if you take care of the uppers, last 20+ years
Classic Formal: Cap Toe Balmoral
If there is a more classic shoe than a Cap Toe Balmoral, I don’t know it.
Simple. Clean. Pair it with a rounded toe, and you’ve got a real winner. The defining feature of the balmorals are the covered eyelets. When it comes to mens fashion, details matter. This detail is the difference between the formal balmoral and the more casual blucher.
The best part about cap toe balmorals? While they are primarily a formal shoe, cap toe balmorals are very versatile. When freshly polished, you can even wear these with a tux. Business meetings and formal events are in your future.
Trendy Formal: Wholecut
Want the trendy take on formal? Go for a Wholecut.
Made of a single piece of leather, a wholecut defines clean. Pay special attention to protecting these as any scuff will show, and avoid wearing these to business meetings unless your whole outfit is fashion forward.
Classic Alternative: Wingtips / Brogues
If you want a classic shoe with a little more flair – try a Wingtip Balmoral.
I love the detailing (known as broguing) of these shoes, but, while they are a classic, they are not for everyone. They are another version of the balmoral, but they are considered less formal. Fortunately in America, these rules don’t matter as much. Feel free to wear them as a replacement for Cap Toes. The one exception? Don’t wear these with a tux.
Trendy Alternative: Double Monkstrap
When it comes to trendy #menswear, the Double Monk is shoe porn of the highest order.
Double Monks are ridiculously trendy right now. Like wingtips, they are less formal than the wholecut, but more historied. These are not as formal as balmorals and may look out of place in a conservative business environment, but if you want to look fashionable or more European – go for it.
Classic Business Casual: Blucher
Like a dress shoe, but a Blucher more open and laid back.
As I said above, most guys won’t even notice the difference between balmorals and bluchers until someone points it out. Traditionally, these shoes are too informal to wear with a suit and should instead be worn in “business casual” situations. Most Americans ignore this, but now you know better.
Trendy Dress Loafer: Horse-Bit Loafer
High Fashion? Go with the Bit Loafer.
The Bit loafer traces it’s roots back to the 1950s and Gucci. That lux heritage made it a favorite of east coast businessmen and Wall Street. That trendy image continues today.
Classic Dress Loafer: Penny Loafer
The Penny loafer fits Business Casual to Weekend in one shoe
A prep school classic. Penny’s have been walking on well-dressed feet for some 80 years, and they won’t stop any time soon. Do yourself a favor and leave the socks at home; do us a favor and bring the foot powder.
Cedar Shoe Tree
This is the simplest and most important thing I’m going to write in this entire post:
Take care of your shoes.
If you are going to spend the money on getting quality shoes, that will last for years, spent the extra $20 bucks and buy a set of cedar shoe trees to go along with them. They will help the shoe maintain its shape, deodorize after a long day, and absorb the moisture from your feet. Ideally, leave the shoes on the cedar trees for at least 24 hours after each wear. That means skip a day. I mean it:
Wait 24 hours after wearing leather shoes before wearing them again
They will last far longer and stay looking great.
What did I miss? What other dress shoes for men do you like? Help us all out by telling us in the comments.
- I wear a couple of pairs of my grandfathers Foot Joy’s to this day ↩