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Shoes and Such

Men’s Dress Shoes: A Complete Guide

Dress ShoesDress shoes. Whether it’s an interview or a cocktail party, every man needs ‘em. And they can’t just be any old dress shoes – they have to look good and feel good, a combination that we’ve mastered.

If you’re trying to determine which footwear you need for your next dressy occasion, then you’ve come to the right place. From oxfords to loafers, here’s your ultimate guide to the dress shoes every man should have in his closet.

The Classic Oxford

First up, oxfords. This lace-up shoe is a classic staple and can range from formal to casual, depending upon the shoe’s styling, color combinations and material. The dressier styles typically include glossier leathers, with black being the most formal color. Silhouettes are typically sleek and tailored, often with a more tapered and elongated toe box. They can be worn with a business suit for a polished professional look at the office, or dressed down with dress pants and a collared shirt. Every man should have at least one pair of these for his two-piece suit. If he wears a suit every day, two or more should be rotated for optimal wear and tear.

DresSports LuxeDresSports Luxe Apron Toe Oxford

The Casual Oxford

More casual oxfords are those everyday shoes a man keeps right at the front of his closet. They’re typically less polished and refined, with a wider toebox and casual materials such as full grain leathers and suedes. Whether it’s for work, a business meeting, or a date night, these versatile oxfords can be worn with almost anything. They can be paired with casual pants or jeans and a sport coat, or can dress up a laid-back outfit like jeans and a button-down. They also come in a wide variation of leathers, suede’s and colors for a more trend-forward take.

Total Fusion Plain ToeTotal Motion Fusion Plain Toe

The Easy Slip-on

Slip-ons are an off-shoot of the classic oxford, as they have similar styling but do not have laces. Many men love them because they can just slip on and go; however they’re typically considered more casual than their oxford counterparts. Like oxfords, slip-ons can run the gamut between dressy and dress-casual, depending upon the design elements. For example, more polished styles with lux full grain leathers that can be worn with suiting. Like oxfords, the more casual versions can include mixed leathers, materials and colors for a more relaxed look. For men that want to add a little flair to their slip-ons, a few other versions are penny loafers and tassel styles.

A13019_SL2BikeSO_MAINStyle Leader 2 Bike Toe Slip-on

The Debonair Wing-tip

A classic style that has made quite a resurgence in men’s fashion today is the wingtip. Wingtips are instantly recognizable by their “wings” around the toecap. Most are brogued with decorative perforations around that front area, and sometimes other areas of the shoe. Like oxfords, they can range from tailored uppers in polished materials for a more formal style, to mixed materials in suede’s and even color blocking. While you can wear them with anything from a suit to jeans and a collared shirt, they should not replace your classic dress shoe. Wingtips are considered more dress-casual than traditional dress shoes, and therefore should be in addition to your go-to dress shoe. They’re more of a casual, trend-forward addition that more and more men are adding to their shoe repertoire for parties or a fun night out.

Total Motion PS WingtipTotal Motion PS Wingtip

The Dapper Dress Boot

If you’re looking for something a bit more rugged than your typical dress shoe, consider dress boots . Chukkas and Chelsea boots (made famous by the Beatles) are two styles we’re seeing on the shelves. They’re built like dress shoes but the vamp is higher and covers the ankle. They can still look sleek and sophisticated tucked under pants, and they’ll make the commute to the office much drier on your feet, especially with styles that feature waterproof technology  And if you’re not ready to wear dress boots to your next boardroom meeting, a variety of the styles listed above also come with waterproof technology.

DresSports WaterproofDresSports Luxe WP Plaintoe Chukka

The Laid-back Loafer

On the much more dress-casual end of the dress shoe spectrum is the loafer. They are slip-on’s but are typically more relaxed in their styling, and feature a slipper-like fit. When traveling to warmer climates, men will often leave their heavier dress shoes behind and opt for a lightweight loafer. They’re a great travel shoe, and can be paired with anything from jeans to chinos. They’re frequently worn with resort wear. Think: a nice dinner out on an island vacation.

Bennett Lane 2Cape Noble 2

As you can see, there are several style options for men’s dress shoes for various tastes and wearing occasions. For some more styling tips, check out our post, ‘Game time, Guys: Up Your Shoe Game’.