How to Buy Dress Shoes: A Complete Buying Guide

Whether you're shopping for your first pair of dress shoes or adding to a well-curated collection, understanding what separates quality footwear from the rest will save you money and ensure lasting comfort. This guide covers everything you need to know.

1. Understanding Dress Shoe Styles

Every dress shoe style has a purpose. Here's what to consider:

Oxford (Balmoral)

The most formal dress shoe. The lacing system is "closed" — the eyelet tabs are stitched under the vamp, creating a clean, streamlined look. Best for business suits, formal events, and weddings.

Derby (Blucher)

Similar to an Oxford but with an "open" lacing system where the eyelet tabs sit on top of the vamp. Slightly less formal but more comfortable for wider feet because the tongue opens wider.

Loafer

A slip-on style that ranges from casual penny loafers to dressier tassel and bit loafers. Ideal for business casual settings and warmer weather when socks are optional.

Monk Strap

Features one or two buckle straps instead of laces. Sits between Oxford formality and loafer casualness. A single monk strap pairs well with suits; double monks work with both suits and chinos.

2. Leather Quality: What to Look For

The leather is the single most important factor in a dress shoe's quality, appearance, and longevity.

Full-Grain Leather

The highest quality. The outer surface of the hide is left intact, preserving the natural grain pattern. Full-grain leather develops a rich patina over time, is breathable, and can last decades with proper care. This is what you'll find in premium dress shoes.

Top-Grain Leather

The surface has been lightly sanded to remove imperfections, then finished with a coating. Still good quality, but won't develop the same character as full-grain. Most mid-range dress shoes use top-grain leather.

Genuine Leather

Despite the name, this is a lower grade. It's made from the inner layers of the hide after the top grain has been removed. It's less durable and won't age as gracefully, but it's the most affordable real leather option.

3. Construction Methods

How a shoe is put together determines its durability and whether it can be resoled.

Goodyear Welt

A strip of leather (the welt) is stitched to both the upper and the sole. This creates a water-resistant seal and allows the shoe to be resoled multiple times. It's the gold standard for dress shoes built to last.

Blake Stitch

The sole is stitched directly to the insole through the upper. This creates a sleeker profile and more flexible shoe, but offers less water resistance. Common in Italian-style dress shoes.

Cemented (Glued)

The sole is attached with adhesive. Less expensive to produce, but the sole cannot be replaced when it wears out. Fine for shoes you won't wear daily.

4. Getting the Right Fit

A well-fitted dress shoe should feel snug but not tight. Here's how to ensure proper fit:

1. Measure in the afternoon. Feet swell throughout the day. Measuring in the afternoon gives you a more accurate size.
2. Leave a thumb's width between your longest toe and the front of the shoe. Your longest toe isn't always your big toe.
3. The heel should be snug with minimal slipping. A small amount of heel slip is normal in new leather shoes — it disappears as the sole breaks in.
4. The widest part of your foot should align with the widest part of the shoe. If the shoe bends at a different point than your foot, it's the wrong shape for you.
5. Consider width. Standard shoes come in D width (medium). If you have wider feet, look for E or EE widths. Narrow feet may need B width.

5. Color Selection Guide

Start with these essentials:

• Black — Required for formal events and darker suits. Every wardrobe needs at least one pair.
• Dark brown (walnut, cognac) — The most versatile color. Works with navy, gray, tan, and earth-toned suits.
• Burgundy/oxblood — Adds personality while remaining appropriate for professional settings.
• Tan/light brown — Best for casual and business casual. Avoid with dark suits or formal wear.

The rule: Your shoes should be the same color or darker than your belt, and should complement (not necessarily match exactly) your suit color.

6. What to Expect at Different Price Points

7. Signs of Quality to Check Before Buying

• Consistent stitching — Even, tight stitches with no loose threads indicate careful construction.
• Leather smell — Real leather has a distinct, rich aroma. Synthetic materials smell like plastic or chemicals.
• Symmetry — Hold both shoes together. The toe shape, heel height, and overall profile should match exactly.
• Sole flexibility — The shoe should bend at the ball of the foot, not in the middle of the arch.
• Last shape — The shoe should follow the natural curve of a foot, not be perfectly straight.