Men's Dress Shoes & Boots Guide

Dress shoes are not merely a luxury, they are a necessity for every man's wardrobe. Even if your style revolves around hoodies or Bermuda shorts, every now and then, you'll need to dress up too. That’s why it’s best to understand the anatomy and style of classic men's dress shoes, so when the time comes to shop, you’ll to able to make the right choice. With that in mind, JCPenney brings you this guide that’ll walk you through the ins and outs of every type of dress shoe for men.

Deconstructing the Dress Shoe

Before diving deep into nuances in style, let’s understand the different components that make up a dress shoe. From front to back, a dress shoe has four parts: toe, vamp, facing, and quarter. It’s the placement and construction of these four parts that help determine the individuality of every dress shoe.

Types of Dress Shoes

The Oxford


Oxfords, the most basic and timeless of dress shoes, gained popularity in 1800s among college students at Oxford University. They were a particularly huge hit because they can be dressed up or down for every occasion. Even today, Oxfords are worn for every occasion, such as work, parties, weddings, and beyond. 

The closed lacing of an Oxford is the most recognizable trait of this shoe. Since the shoe’s facing is attached beneath its vamp, it has a slim silhouette that hugs the foot’s contour.

Style Recommendation

• For everyday wear, choose Oxfords in brown in both leather and suede. Reach for bright socks.
• For business attire, dark brown, tan, and black are your safest choices. Keep the look classic with a darker pair of socks.

The Loafer


Loafers are known for their slip-on style, which is inspired by moccasins. They were originally made for King George V of England in the 1930s, but gained popularity only in the 1960s when American businessmen and lawyers started wearing them with suits. 

Loafers usually have a saddle, which can be plain, or feature a slit (like penny loafers) or metal ornament. They can also have a tassel hanging from the saddle and an elevated seam running along the toe.

Style Recommendation

• For formal occasions, pair clean loafers with a suit or a pair of embellished loafers.
• For a more casual look, pair with rolled jeans and a pair of colorful socks.

The Dress Boot


Dress boots are short lace-ups made like oxfords, but with longer shafts. This shoe style dates to the Victorian era when men had little choice in footwear. Dress boots quickly became a must-have for formal day wear, and they remain an appealing alternative to traditional dress shoes to this day. 

Most dress boots are made of the same material as Oxfords, and they're usually the same length as Oxfords. This short, lace up boot may also have wingtip brogues on the toe of the boot and along the seams. 

Style Recommendation

• Dress boots are the most formal style of boots and may look better with dark-colored jeans.

The Chelsea Boot


The Chelsea boot dates back to Victorian England and is said to have been invented by the Queen's boot maker, J. Sparks-Hall. Chelsea boots quickly became a practical alternative to the stiff Victorian boots of that time, and were soon adopted by horse riders. In the 1960s, Chelsea boots saw a lasting resurgence when they were worn by The Beatles as part of their British Mod style. 

These boots are ankle length, with rounded toes and low heels. The gusset on the sides allows you to slip them on and off without losing the refined look of a lace-up boot. The fact that there are no laces adds to the Chelsea's slim, clean look. In the more formal versions, the Vamp and Quarter boots are made from one piece of leather which minimizes stitching for a neat look. 

Style Recommendation

• Classic Chelsea boots aren’t embellished. Their simplicity elevates them to a level that elevates jeans to the next level and traditional suits to the next level. If you buy Chelsea boots, wear them on their own as part of your casual or dressy-casual look.

The Chukka Boot


Chukka boots are lace-up boots with only 2-3 eyelets on either side. They come from the sport of polo, where a "chukka" is a seven-minute segment. A match can consist of 4, 6, or 8 chukkas, depending on the game. Some people think of chukkas as a shorter version of the boots that polo players wear, while others think of them as after-game shoes for polo fans, similar to how the original Uggs were meant for surfers. 

Chukka boots are ankle length boots with no eyelets. Because there aren’t many eyelets, the short shaft allows for a comfortable fit that doesn’t affect your trouser shape. Chukkas also have a round toe, and the classic chukka boot is usually made from soft suede.  

Style Recommendation

• Chukkas are great to wear with smart-casual attire, making them perfect for the office, a night out with friends, or daytrip with family.

Dress Shoe Toe Styles

Plain Toe


Plain toe shoes have unadorned vamp for a look that’s clean and unassuming.

Cap Toe


Cap toes have a horizontally stitched line across the vamp that “caps” the toe. 

Wingtip


A winged cap that peaks in the middle of the toe is the trademark of this toe style. The wingtips often have brogueing in the center of the toe and along the seam of the cap.

With all this information in mind, you’ll now be able to make the most informed purchase possible when choosing your next pair of men’s dress shoes. And remember – when shopping for quality dress shoes and boots, they are an investment for your wardrobe and a signature of your personal style. Whether you're preparing for a big job interview or dressing to impress at a wedding, we've got you covered – check out our guides on how to dress for a job interview and wedding attire guide for more expert style advice. Shop the full collection of men’s dress shoes and boots online at JCPenney today!