Best Dress Shoes 2021: Reviews of Top Oxfords, Boots, Loafers for Men - Rolling Stone
Home RS Recommends Lifestyle

How to Find a Good Pair of Dress Shoes Online (Plus 6 Top-Rated Pairs to Buy)

The right (or wrong) footwear can truly make or break an outing, so here’s how to find the best dress shoes for any occasion

The man wears shoes. Tie the laces on the shoes. Men's style. Professions. To prepare for work, to the meeting.The man wears shoes. Tie the laces on the shoes. Men's style. Professions. To prepare for work, to the meeting.

iiievgeniy -

If you purchase an independently reviewed product or service through a link on our website, Rolling Stone may receive an affiliate commission.

Nowadays, picking up a pair of dress shoes may not be the first thing on your mind, especially if you’re not sure when your next big event is going to be. But the truth is, the best dress shoes are a worthy investment, your wardrobe’s secret weapon to helping you feel confident and comfortable. They’re as necessary to any formal occasion as picking up a well-fitting tie.

Whether you’re finally stepping out for a night of live music again, attending a premiere, or dressing to impress for a job interview, there are just some occasions that require putting away your usual kicks and getting a little classy (although there’s something to be said about always having a solid pair of sneakers handy).

There are a variety of styles and options, but we’re gonna be real here and say this is not the piece of your ensemble you want to tighten your purse strings on. Of course there are budget-friendly pairs out there, but you’ll want to throw a few bucks at some good-quality dress shoes you can still wear years down the line. The key is knowing what materials to look for, and choosing versatile styles that you won’t only break out for black tie events, or and won’t wear down after a couple social gatherings.

How to Find a Good Pair of Dress Shoes

We’ve also chosen dress shoes that can fit into any wardrobe, and feel as timeless as they are trendy. These shoes are designed not just to look good, but have maximum support, cushioning and breathability, so you can focus on having a good time and not worry about a stiff pair that will pinch your toes.

Style: Oxfords are typically the staple of dress shoes, and have a signature closed lacing look—they’re usually best for business and formal events, as well as dinner dates. Depending on the type of heel and arch support your pair has, they might not feel so great for all-day wear. Derby, Loafers, and Monk Strap styles tend to be more comfortable, but are also more appropriate for smart-dress casual events, or for wearing to in to the office.

Material: Ironically enough, the most rugged and resilient shoe materials are often considered the least formal. Smooth leather is the gold standard for dress shoes, but anything else such as canvas, suede, and pebbled leathers get more casual (the same goes for rubber soles, which are more practical for everyday use, but less formal). Consider how often you’ll be breaking out these shoes, and whether you’re looking for something you can wear every day, or just once in a blue moon.

Fit and Comfort: You should know your shoe size anyways, but having an accurate fit isn’t the only criteria that will affect how comfy your pair will feel. Consider that some dress shoes measure how wide or narrow the fit will be, regardless of regular sizing. Certain styles like slip-on loafers will also just be a bit more comfortable long-term, especially if you have a high arch or instep that will strain against formal dress shoes.

What Are The Best Men’s Dress Shoes?

The right (or wrong) footwear can truly make or break an outing. If you’re heading back to the office, or even attending any remotely formal event anytime soon, you’ll want to step out in one of these pairs of top-rated dress shoes. These shoes win points for comfort, versatility and overall style.

1. amberjack The Original

Amberjack The Original Dress Shoe


Amberjack’s The Original aren’t your dad’s Oxfords, but they’re quite possibly the best dress shoes, period. They use A-grade full grain leather, and a buttery-soft sheepskin lining, which is specially engineered to provide both flexibility and near unbeatable comfort. Cushioning comes from a “thermo-moldible” insole that’s similar to memory foam, but uses your own body heat to conform to the shape of your feet, hugely reducing fatigue.

The sole is a custom TPU that have an athletic-type build in the front, but hiking boot material in the back. Speaking of looks, we can confidently say we’re fans. The Original shoes have a durable, yet refined build, making them suitable for a range of outfits from casual to fancy.

Buy: amberjack The Original at $179

2. Wolf & Shepherd Ringer Loafers

Ringer Loafer

Wolf & Shepherd

If you’re looking for a staple pair for casual Fridays, these premium Ringer Loafers from Wolf & Shepherd are a great pick. Created by a former Adidas designer, the highlight is the “FloatForm” memory foam throughout footbed that allows real sneaker-level comfort so you can stay on your feet all day. The padded heel collar has a suede lining for reduced slippage (you might not even need socks). Combined with a super soft, abrasion-resistant sheepskin lining, and you’ve got a seriously comfortable shoe. These are built to last, with leather treated with custom-blended formula for durability. And the hybrid dressy-casual look works well for both weekends and formal events.

Buy: Wolf & Shepherd Ringer Loafers at $179

3. To Boot New York Ultra Flex Conner

Ultra Flex Conner


For a shoe you can dress up or down, consider this Ultra Flex Conner pair from To Boot New York. Supple Italian leather makes up the upper, with a monk strap buckle closure, but the shoes are still surprisingly flexible. The lining itself was constructed with breathability in mind, ensuring you won’t want to kick these off after a long party. The shoes also use a cushioned leather footbed, that will put a comfort spring in your step all day. Plus, we agree with To Boot New York that these kicks are less formal than a lace up Oxford, but more polished than a loafer. You’ll look put together no matter what you throw on on top of this pair.

Buy: To Boot New York Ultra Flex Conner at $319.99

4. Magnanni Leather Monk-Strap Dress Shoes

MAGNANNI Leather Monk-Strap Dress Shoes

Saks Fifth Avenue


These Magnanni Leather Monk-Strap shoes are worthy of a serious wardrobe upgrade. Available exclusively at Saks Fifth Avenue, all of the shoes’ premium features, like the handcrafted medallion perforations down to the sleek monk strap, are handmade in Spain. The soft leather lining and sole are thoughtfully detailed to be as flexible as a dress shoe can get. But, despite the sophisticated look, they’re still very comfortable. Basically, the quality craftsmanship is absolutely worth the price tag, from the padded insole, to the glove-like fit. Available in two sleek colors, they’ll actually make you want to break out a suit jacket.

Buy: Magnanni Leather Monk-Strap Dress Shoes at $191.19

5. Thursday Boot Co. Scout Chukka Boots

Scout Chukka Boots

Thursday Boot Co.

These Scout Chukka boots are an example of where the future of dress shoes is headed. The streamlined silhouette and high-end construction is very modern, but they still look as purposeful for running errands as they would in the boardroom. The materials, including a brown chrome leather upper and stitched outer layer, also give a cleaner look than say, construction boots. But they offer some upscale details, such as a water-resistant finish, and a shock absorbing insoles that also have a microbial treatment, so they can stand up to the demands of being on your feet year after year. This makes the Scout boots the best pick if you don’t like the fit or feel of traditional dress shoes.

Buy: Thursday Boot Co. Scout Chukka Boots at $149

6. Stacy Adams Abbott Cap Toe Oxford

Cap Toe Oxford


You don’t always have to sacrifice style for price, and these Stacy Adams Abbott Cap Toe Oxfords are proof of that fact. This pair boats a classy dark leather upper with perforated detailing, a classic design that gives you endless styling options. While these budget-friendly shoes aren’t ideal for every occasion, they’re great for putting together a more polished outfit for dressy-casual events. What they may not be best for is long-term wear—the footbed is only lightly cushioned, and though the rubber sole is slip resistant, you couldn’t exactly pound the pavement with these. That being said, they won’t break the bank, and they’re sure to be the star of any outfit, whether you throw them on with jeans or khakis.

Buy: Stacy Adams Abbott Cap Toe Oxford at $44.97

In This Article: Fashion, footwear, RS Recommends


Powered by
Arrow Created with Sketch. Calendar Created with Sketch. Path Created with Sketch. Shape Created with Sketch. Plus Created with Sketch. minus Created with Sketch.