The square-toed men's dress shoe has become ubiquitous.
Somewhere along the line guys seem to be getting the idea that a dressy shoe is a flat, squarish one.
They're everywhere, especially stores that sell mass-produced men's shoes fairly cheaply.
If you only own one pair of dress shoes, they should not be this style.
In fact this men's shoe style is not at all classic, and only looks acceptable with a few style and body types.
Please note square toes aren't inherently bad.
Other men looking to add a little visual bulk — very slender or undersized men — can benefit from the widening effect.
They have their place.
But they're hardly a fashion be-all and end-all, and for the vast majority of men there are better footwear options.
Pointed Toe Men's Shoes
- Good for small/short feet
- Help add an impression of length/height to a man
- Appropriate for all levels of formality
Your basic pointed-toe or narrow-toe dress shoe is a flexible style that works great for anyone with smaller feet.
Everything from formal black oxfords to casual moccs look fine with narrow toes.
Avoid the cowboy-boot extreme unless you're deliberately wearing a Western style — pointed doesn't mean triangular, just tapered — and you should be set to wear pointed-toe shoes just about anywhere.
Cap-Toe Men's Shoes
- Help shorten the impression of large feet
- Add an extra visual element to make shoes more interesting
- Suitable for most levels of formality
A cap-toe can be added to just about any style of shoe, including narrow toes or the square-toes we're suggesting alternatives to. Cap toes have a seam across the front of the shoe, perpendicular to the wearer's leg.
There may be an extra leather “cap” actually in place over the toe, or more commonly the seam simply joins two pieces of leather; occasionally the shoe is actually a single solid piece of leather and the seam is strictly decorative.
The effect shortens the foot's visual impression, making it a good style for men with large, long feet.
Very formal black dress shoes meant for the most serious business and social occasions should stay as simple as possible, but any other shoe in your collection will do just fine with cap toes.
Split-Toe Men's Shoes
- Uncommon and distinctive style
- Helps draw attention to shoes without shortening their visual appearance
- Appropriate for most settings
Split-toe shoes are something of a rarity. A vertical seam — the “split” — runs down the front of the toe, which wraps around like a more restrained wingtip.
This adds a bit of visual interest to the shoe without breaking the vertical lines up, making it a better choice for smaller men than the horizontally-oriented cap toes.
Like a cap-toe shoe, split toes can be worn at most levels of formality, but not the strictest of business dress.
Medallion Men's Shoes
- Decorative, punched-leather pattern
- Suitable for business-casual or casual wear
Decorative leather punching is called “brogue” styling on men's shoes, and is referred to as a “medallion” if the tooling is limited to the toe of the shoe.
A medallion toe can work with any shape, but is most common on pointed or wing-tip toes.
The more tooling a leather shoe has, the less formal it becomes .
Medallion shoes can be anything from fairly dressy business wear to an entirely casual option.
Wingtip Men's Dress Shoes
- Highly decorative style
- Works well with a variety of casual ensembles
If you're looking to make a statement, wingtips are the way to go.
The decorative style is on the casual side, and will usually only be seen on point-toed shoes.
Wear it any time you want your footwear to be actively decorative and noticeable.
Wingtips work well on boots or on brogues and slip-on moccasins, but keep them to your casual wardrobe. They're usually not good businesswear, unless you're working in a very casual setting.
Two-Tone Men's Shoes
- Very decorative style
- Distinctively “retro” look
Two-tone shoes are eye-grabbers. Expect to attract attention and comment if you wear them!
Save the style for social occasions — it's too flashy for business settings — but keep it in mind for your dancing clothes.
A two-tone shoe adds a classic twist to a modern outfit.
Try to avoid wearing them with anything else distinctively “retro,” though, or you'll risk looking like you're just wearing a costume instead of a style.
Most of these shoes are easy to come by — ask at any good men's shoe store (not a generic or department store), or shop around online.
The internet's done wonderful things for shoe shopping, and even men with unusual sizes can usually get a good selection.
So with all that choice…skip the pilgrim shoes.