Men’s Dress Shoes Style Guide

From staying polished on work days to looking sharply casual on weekends, dress shoes say a lot about a man.

Choosing pairs with select design details and caring for them properly is only half of the equation. The other half involves finesse to pair them with the right outfits and occasions.

Check out this men’s dress shoes style guide to see why you only need a few high quality, sensible pairs to look great.

10. Lace ups

Most men need at least one good pair of lace up dress shoes to complete their wardrobe. These are a safe, classy choice for any situation from dinners with colleagues and networking events, to weddings, dinner parties and job interviews. Dark colors are versatile and pair well with formal and casual wear. If you tend to dress more on the casual side, a pair of chocolate-browns go best with jeans, khakis and gray slacks.

9. Penny loafers

Modern penny loafers are not the same frumpy slip-ons that may first come to mind. Today’s designs are narrow, and sleek and they adapt to any outfit you wear them with whether it’s jeans or formal wear.

8. Sneakers!

Good news, athletes and weekend warriors: Low-top sneakers are slowly sneaking their way into conferences, offices and glittery events, particularly in the tech industry. As long as you stick with darker colors and muted designs (no neons), sneakers plus suit equals a more youthful look. They work best with off-beat suits that are either slim or laid back, not traditional.

7. With wingtips

No men’s dress shoes style guide would be complete without a nod to classic wingtips. This is a timeless feature because it lends polished ruggedness to any ensemble. A good pair of wing tips is a reliable go-to, but you must keep them clean. Detailing draws the eye downward, which is not what you want if your shoes are scuffed.

6. Dare to bare

Hey, if you can pull off a pair of sandals wherever you go, do so! Baring your feet is a risk in professional environments, but the confidence it takes to do so goes a long way. While not recommended for your next black tie occasion, try them with khakis or dark slacks for a slightly unbuttoned, formal occasion like a wedding on the beach.

5. Slip-ons

The best thing about slip-ons is that they sort of feel like house shoes, but they’re perfectly acceptable for fancy occasions. If you’re the kind of dresser who wants to look good without taking a lot of time or money to do so, slip-ons are made for you. Orthotic slip-ons offer both style, and the comfort and extra support men with foot pain require.

4. Fear no rubber sole

More and more men are taking rubber soles for a walk and liking what they feel. You don’t yet see them on every men’s dress shoes style guide because they’re not perfect for everyone. The drawbacks are that once rubber soles wear away, that’s the end of the line. Replacing the heels or adding taps to protect them only works with leather soles. That said, rubber is comfortable and a much better choice in wet weather.

3. Boots?

Yes, boots. Wearing sharp, polished boots with a nice suit tells the world you do what you want (and do it well). It’s silly to wear your best Oxfords when it’s cold and pouring. Boots are a sensible alternative. The catch is they have to look good – clean military style, leather lace-ups that end above the ankle – and you must pair them with a tailored, fashionable suit.

2. Fine leather

If you want the real deal, go with hand-crafted men’s shoes made from fine leather. When cleaned regularly, leather shoes actually look better with age and the soles gradually mold to the bottoms of your feet so they get more comfortable. Small details like a single strap with a basic buckle adds a subtle touch to style.

1. Black staples

Basic black slip-ons can be dressed up with a suit or toned down with fitted jeans. No frills necessary with this style. In fact, the simpler the better. Keep them polished and you’ll always have them ready to slip on whether heading to a meeting or out on a date.