The 13 Best Shoes for Male Teachers

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It doesn’t take a degree in pedagogy to understand why guys would want to find the best shoes for male teachers.

If you’re not wearing supportive and comfortable shoes, a long day spent standing at the front of the class can wreak havoc on your body.

Unfortunately for those who also want to look sharp, there’s often a huge chasm between comfy shoes and stylish shoes.

That makes it hard to find a pair that’s supportive enough to wear on a daily basis, but sharp enough to maintain a put-together and professional look.

The good news is that teachers aren’t alone in wanting a good pair of shoes that combines a comfortable fit with a stylish design.

Shoe manufacturers have finally taken up the cause, and started making comfortable footwear that also happens to look great.

In this post I’ve put together a list of the best shoes for male teachers who want comfort and support without sacrificing style and design.

The (Absolute) Best Shoes for Male Teachers

Breaking Down the Most Stylish & Comfortable Teacher Shoes for Men
Overall Best Shoes for Teachers ↓

Wolf & Shepherd 

Crossover™ Longwing

Wolf and Shepherd Crossover™ Longwing
  • 4.8 Stars
    • 421 Reviews
    • Available in five different colors

Combining the comfort of tennis shoes with the quality and style of dress shoes, Wolf & Shepherd’s Longwings are easily the best work shoes for teachers.

The shoe’s upper is made from Italian full-grain leather and boasts the kind of sharp, stylish toe shape you usually only find on luxury leather shoes.

But underneath the sharp exterior, they’re all about comfort.

In addition to a super soft lining that’s abrasion-resistant, they come with a removable memory foam footbed that provides all day comfort and a high-traction thermal rubber outsole that’s soft, durable and forgiving.

Promising Review:

Extremely comfortable and look really good.

A modern day dress shoe that works worth a suit and tie or with chinos or jeans.

– Shaun S.

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The Original

Amberjack The Original
  • 4.9 Stars
    • 151 Ratings 

A close runner up to the Wolf & Shepherds above, Amberjack’s Originals are another pair of high quality shoes that look great, feel even better, and are available in a variety of colors.

No less an authority than GQ called the Originals “the world’s most advanced dress shoes,” and it’s not hard to see why.

On the outside, they have a grade-A leather upper that’s sourced from one of the world’s best tanneries.

Under the hood, they skip the memory foam insole in favor of a heat-activated option that molds to the shape of your foot, helping it last longer.

(Which is especially beneficial to teachers who spend a long time on their feet.)

And down below, they’ve got a custom-designed TPU sole that provides just as much comfort and durability as a traditional rubber sole, but manages to be sleeker and sharper-looking.

Promising Review: 

Having worn dress shoes for work for years, I have to say to say these are some of the most comfortable shoes I have ever worn.

The shoes have the comfort of a gym shoe but the style of a dress shoe. Brilliant! 

– Frank S.

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Atticus LT Lace

Clark’s Atticus LTLace
  • 5 Stars
    • 1 Rating 

Clark’s Atticus model is another great option for all day wear.

Both the foam footbed and the EVA outsole are made from recycled content, which helps make them eco-friendly and lightweight shoes.

Plus, the interior features a breathable leather sock that’s great for going barefoot, so you can ditch the socks at the end of the school year when the weather heats up.

But the best thing about the Atticus might be the affordable price:

It’s hard to find a great pair of shoes for less than 200 dollars these days, but the Atticus is squarely in the 100 to 150 dollar price range, making them the perfect shoes for teachers on a tight budget.

Promising Review: 

I bought Clarks for the support, and as a teacher who is constantly on his feet,

I appreciate the support and comfort that Clarks is known for providing! 

– woodin

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Johnston & Murphy 

XC4® Wingtip

  • 4.5 Stars
    • 35 Ratings 

Johnston & Murphy’s entire XC4 line is designed with comfort and support in mind.

But their brogued Tanner model is a particular stand out thanks to a sophisticated toe shape that looks almost as good as many normal dress shoes.

Inside, a blend of sheepskin and mesh materials combine comfort and performance into a soft and breathable interior lining, providing the kind of comfortable feel that will hold up over long periods of time.

Promising Review: 

I bought two pairs of these on a recommendation from a friend. No regrets. These have to be the most comfortable dress shoes I own.

Being flat-footed makes it a challenge to find good shoes. These fit the bill and then some.

– Timothy L.

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Clark’s Chantry Wingtip
  • 5 Stars
    • 1 Rating

Another good option from Clark’s, these ones have many of the same comfort and support features as the Atticus listed above, including a cushioned insole and real leather upper.

But these ones also come up with tab on the back that makes them easier to slip on, so they’re great for teachers who don’t want to fuss with laces.

Promising Review: 

I bought this pair for work and I have received nothing but compliments. Great quality, feel and look. Highly recommended. 

– shelkesid

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Cole Haan

ØriginalGrand Wingtip Oxford

Cole Haan ØriginalGrand Wingtip Oxford
  • 4.8 Stars
    • 681 Ratings 

Probably the most popular brand on this list, Cole Haan is something of a pioneer in the comfortable dress shoe game, and a great place to turn for a new pair of shoes.

The Original Grand Wingtips combine a cushioned synthetic sole with a soft genuine leather upper, resulting in stylish and supportive shoes that work well for (just about) any teaching job.

Promising Review: 

Extremely comfortable and stylish. I’ve had a lot of compliments at work. I love wearing these. Definitely have to buy another pair. 

– LG

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Essential Details Waterproof Wingtip

Rockport Men’s Essential Details Waterproof Wingtip Oxford Shoe
  • 4.5 Stars
    • 640 Ratings 

Another wingtipped model, this dress shoe from Rockport sports a cushioned footbed that’s actually made by adidas.

It gets rave reviews on Amazon because it offers the comfort of a sneaker in the shape and style of a dress shoe.

It’s the perfect way to pass muster with your school’s dress code, while still getting the kind of additional support and comfort you’d expect from athletic shoes.

Promising Review: 

Most dress shoes I’ve owned have been extremely uncomfortable. They either pinch my toes or offer no support.

These Rockport shoes are the exception. I’m able to wear them all day and walk around the city without ever feeling uncomfortable.

They’re also waterproof, which is great when it rains. Highly recommended.

– Donnie

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Wolf & Shepherd 

Crossover Loafers

Wolf & Shepherd Crossover Loafers
  • 5 Stars
    • 155 Ratings 

These loafers from Wolf & Shepherd are easily the best slip on teacher shoes.

Penny loafers are always dapper, but often come with a razor-thin sole that looks great but can lead to sore feet at the end of the day.

But this version combines a sharp toe shape with a thickly cushioned rubber sole, making them perfect for daily wear teaching shoes.

(Not to mention a lot more attractive than the Dansko clogs we recommend for other professions like nurses and doctors, where slip on shoes don’t have to be stylish.)

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Johnston & Murphy

XC FLEX™ Cody Longwing

Johnston & Murphy XC FLEX™ Cody Longwing
  • 4.5 Stars
    • 25 Ratings 

I love these wingtips from Johnston & Murphy because they’re bad-ass brogues that also happen to flexible, comfortable and supportive.

The brogued, genuine leather upper sits on top of a lug tread footbed made from lightweight synthetic material, making them a great fit for teachers who walk to work.

(Or those who just want a stylish pair of brogues that will impress their fellow teachers.)

Promising Review: 

The look is classic, they feel very comfortable and the sole seems well-built.

They were comfortable out of the box and are now even more comfortable after being broken in a bit.

Overall I am very pleased with them and will buy them again.

– Scott

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Hush Puppies

Men’s Bennet Wingtip Oxford

Hush Puppies Men's Bennet Wingtip Oxford
  • 4.3 Stars
    • 20 Ratings 

This shoe from Hush Puppies is billed as a wingtip, but the broguing is so subtle that it’s more of a hybrid between a wingtip and an oxford.

Underneath the soft, genuine leather upper is Hush Puppies’ padded and uber-comfortable footbed, making this an ideal shoe for those with high arches, heel pain or other foot-related ailments.

Promising Review: 

SThese shoes are soft and amazingly comfortable. Highly recommended.

– John49

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Cole Haan

Grand Ambition Postman Oxford

Cole Haan Grand Ambition Postman Oxford
  • 4.4 Stars
    • 33 Ratings 

Named for another profession that requires a lot of time spent on your feet, Cole Haan’s Postman oxfords also happen to make great shoes for teachers.

The upper is made from a combo of leather and nubuck, giving them a dressedy-but-not-stuffy vibe, while the dual-density EVA outsole provides the comfort and support Cole Haan is known for.

Promising Review: 

Great shoes! Super comfy and great looking! 

– Christian R.

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Un Tailor Cap Toe

Clark’s Un Tailor Cap Toe
  • 4 Stars
    • 4 Ratings 

I have a strong preference for cap toe shoes, which in my opinion just look a little more dapper than regular oxfords or derbies.

This model from Clark’s combines the sophistication of cap toes with the comfort of dual-density ortholite footbeds, making them an excellent option for those who want to feel supported while looking sharp.

Promising Review: 

I bought this pair for comfort & for the look of the shoe.

Nice shade of brown that fades darker slightly at the toe. Pairs well with Khakis. 

– Bmoney

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More Resources ↓
More Men’s Shoe Advice to (Lame Pun Alert!) Step Up Your Style:
More Insight on How to Look Good & Live Well:

The Recap ↓

Overall Best Shoes for Male Teachers

Dave Bowden

Wolf & Shepherd Crossover™ Longwing


Combining the comfort of tennis shoes with the quality and style of dress shoes, Wolf & Shepherd’s Longwings are easily the best shoes for male teachers.


Banner image: Rido / Shutterstock

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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