Style Guide: The Best Socks to Wear with Loafers

The loafer is one of the most versatile shoes in any closet. Whether you're heading to the office, out for brunch, or dressing up for a special occasion, loafers work across dress codes, for him and for her. But there's one question that trips people up: what socks should you actually wear with them?

The right sock can pull your whole outfit together while keeping you comfortable from morning to night. The wrong choice can throw off your whole look. At World's Softest, we make socks that look as good as they feel. Here's everything you need to know about pairing the perfect sock with your favorite loafers.

Matching Socks to Your Loafer Style

Not all loafers are created equal, and different styles call for different sock approaches. Here's how to get it right.

Penny Loafers & Classic Loafers

The penny loafer is the most versatile loafer style out there. You can dress it up for formal occasions or keep it relaxed for casual outings; It all depends on what you pair it with.

For a polished look, reach for dress socks in solid colors that match your trousers. This creates a seamless line from pant to shoe. For something more laid-back, crew socks in complementary colors work beautifully.

Our pick: The 1902 Crosstie Crew offers a subtle ribbed texture that looks sharp with classic loafers while delivering the softness you'd expect from us.

Dress Loafers & Tassel Loafers

Tassel loafers and dress loafers lean more formal. These are the shoes you wear with dress pants to the office or out to dinner. They call for dress socks in solid colors or subtle patterns; Nothing too bold or casual.

Stick with navy blue, black, or deep tones that complement your outfit. Avoid bulky socks that bunch up in your shoe.

Our pick: The 1902 Metro Ragg Crew has a sophisticated marled look that pairs perfectly with dress loafers while feeling incredibly soft all day.

Suede Loafers & Leather Loafers

Here's where you can have a little more fun. Suede loafers have a naturally casual vibe, so they pair well with textured or patterned socks. Think marled designs, stripes, or rich colors like forest green or burgundy.

Leather loafers can go either direction. A sleek black leather loafer works for formal events, while a brown leather loafer feels right at home on the weekend.

Our pick: The 1902 Metro Cotton Ragg Rugby Crew adds just the right amount of personality with its striped pattern and fun colors, great for suede loafers and weekend outfits.

Brown Loafers vs. Black Loafers

Wondering which sock colors work best? Here's a quick guide:

Brown loafers give you more flexibility. Earthy tones and jewel colors all work well. 

Black loafers look best with darker, more formal shades.

One rule for both: skip the stark white socks; Save those for the gym.

Sock Length: Finding the Right Fit

The length of your sock matters just as much as the color. Here's how to choose.

No-Show & Low Socks

You've probably seen the sockless look. That bare ankle aesthetic that's popular in warmer months. It looks clean and effortless, especially with casual loafers, boat shoes, or rolled-up jeans. But going truly sockless has its downsides: it's not great for your feet and it's definitely not great for your shoes.

The solution? No-show socks give you that sockless look without the drawbacks. You get the clean aesthetic with all-day comfort and protection for your loafers.

Our pick: The Weekend Liner disappears into your shoe while keeping your feet happy. Perfect for summer and casual looks.

Crew Socks

Crew socks are the most versatile length for loafers. They work in both professional and casual settings. Plus, they stay in place throughout the day, with no tugging or adjusting.

For him, our 1902 collection offers crew lengths that pair perfectly with loafers. For her, our Classic Crew and Weekend collection hit the mark.

Seasonal Considerations

Warm Weather

When temperatures rise, lighter-weight socks or no-show options are your best bet. This is when the bare ankle look feels most appropriate. Focus on comfort and keeping cool.

Cooler Weather

In colder months, crew lengths keep you comfortable without adding bulk. If you want extra warmth, wool socks are a great choice. Our World's Softest Wool collection offers medium-weight options you can wear year-round.

Common Mistakes to Avoid

White athletic socks with dress loafers. This is the classic mistake. Athletic socks belong at the gym, not with your loafers. Keep your look polished.

Mismatched formality. Don't pair casual ankle socks with dress loafers at formal events. Match your socks' vibe to the occasion.

Ignoring comfort. A great-looking sock that hurts your feet isn't worth it. That's why we focus on softness first; You shouldn't have to choose between style and comfort!

The visible sock gap. If your sock slips down and shows skin between your pant and shoe, it's time for a longer length.

Our Top Picks for Loafers

Here are some of our favorite World's Softest socks to pair with your loafers. 

For Him

1902 Crosstie Crew – Subtle ribbed texture in classic colors like black and navy. Perfect for desk to dinner.

1902 Metro Ragg Crew – Marled design that adds visual interest. Great for penny loafers and casual leather loafers.

1902 Metro Cotton Ragg Rugby Crew – Striped pattern for a bit of personality. Works with suede loafers and weekend outfits.

For Her

Classic Crew – A timeless choice in a range of colors. Soft enough for all-day wear with your favorite loafers.

Weekend Ragg Crew – Fun textures and patterns for casual loafer looks. Perfect for weekends and relaxed office settings.

Weekend Liner – For the sockless look without going sockless. Ideal for warmer months and casual loafers.

Find Your Perfect Pair

The right socks can make or break your loafer look. Whether you're dressing up for a special occasion or keeping it casual on the weekend, there's a perfect pair of socks waiting for you.

At World's Softest, we believe style shouldn't come at the cost of comfort. Our socks feel as good as they look. Because when your feet are happy, everything else just falls into place.

Explore our collections and find your perfect pair.