Best Dress Shoes for Men that are Classy & Comfortable (2019)

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“Who notices a man’s shoes,” Red narrates in Shawshank Redemption, as he tells the story of his friend’s escape from the brutal prison in expertly polished dress shoes.

Who indeed?

Unless you’re escaping from prison like Andy Dufresne, lots of people notice a man’s shoes. A good pair of dress shoes is easily one of the most important purchases a man can make.

In this article, we’ll go over a few of the things you need to be thinking about when you’re shopping for dress shoes, like style, material, intent, price, and lacing. We’ll round up a list of the best shoes for all kinds of occasions and budget as well as take a look at how you should care for your shoes, so they last as long as possible.

Finally, we’ll take a look at how a dress shoe differs slightly from a dress boot and how you can wear each for a variety of different occasions.

Let’s get started.

In A Hurry? Our Top Picks:

What to Know When Buying Dress Shoes

As we got deep into the research, we identified nine key factors that you should think about before buying dress shoes, here’s what you need to know:

1. Style

From Oxford to Derby, laces to loafers, your options when it comes to men’s dress shoes are plentiful.

You can find dress shoes in a variety of different styles, cuts, colors, and materials, each to fit the need of the occasion or preference of the man.

There are a few common types that you should look for:

  • Derby & Oxford: Your go-to dress shoe for virtually all occasions, the only real difference between these two types of footwear are the laces. Derby shoes feature an open flap, while the Oxford has a closed flap over the laces. The timeless, elegant, and simple design of both types means you can wear them anywhere, for anything.
  • Loafers: Always good to have in the closet, a good pair of loafers can build a sense of style without the need to tie any laces. Designed to be paired with any outfit (except shorts, if you please), loafers allow for more decoration of the top of the shoe, if desired, because of their lack of laces.
  • Single & Double Monk: Monk shoes are designed with a single or double buckle closure that comes over the top of the shoe. They are somewhere in the middle of formal and casual footwear. You wouldn’t wear them to a black-tie event, but you also wouldn’t want to wear them with a t-shirt. When worn correctly, however, the monk shoe can elevate any outfit.
  • Formal Pumps: The most formal of shoes, Opera pumps as they are often called, are typically slip-on with scant decoration – just a grosgrain ribbon on the cap. They’ve been worn to the most formal of events since the 1800s, and their simplistic, sleek design has kept them in style.
  • Dress Boots: There are lots of options when it comes to boots. From the very formal style of an actual dress boot to the more simple, casual Chukka style, dress boots have been worn with a variety of different outfits for hundreds of years. We’ll dive more into them below.

2. Material

Leather has been used for men’s shoes for millennia because it is incredibly versatile, stylish, and easy to care for compared to other materials (as we outlined in our recent guide how to clean and care for leather). There are a few different types of leather to keep an eye out for when you’re shopping.

Full-grain leather is the most natural and least processed leather option. Despite that, it is the least common and most expensive of the leathers. Full-grain leather is also inherently imperfect – because it is the least processed, it often contains small scars or patterns in the hide.

Top grain leather is full-grain leather that has been sanded or otherwise processed to provide a smooth, clean look. Top grain removes many of the slight imperfections, but doing so reduces the strength of the product. This is often beneficial for retailers and companies that want to make a consistent product. Additionally, the removal of the top layer of leather will provide a consistent look throughout the life of the shoe.

Nubuck leather is again similar to the one above it in this article, but instead of having the full-grain processed, it is buffed, brushed, and polished to provide a robust and velvety material.

Calfskin leather can be processed in many ways but is essentially the same as top grain leather, just from a young cow. Calfskin was traditionally used for parchment and vellum and is now used in many high-end clothing and shoes (source).

Suede is made from the underside of the animal hide, which is softer and more pliable, as opposed to the top or full-grain, which provides a sturdy shoe. A whole host of fabrics are often manufactured to have the appearance of suede leather.

Leather, when properly cared for, can easily last several years and provide comfort and style throughout. By far, it’s the best ROI if you plan on getting a dress shoe.

There are other types of materials, like humanmade fabrics, such as polyester. Shoes are also increasingly made from materials like wool and cotton, as well. You can find these shoes at several large retailers. These materials, however, don’t offer the best bang for your buck – either with your wallet or your fashion sense – as a traditional leather dress shoe.

3. Intent / Occasion

When you’re selecting a dress shoe, one of the most important factors to consider is the occasion to which you wear it and the statement you’re trying to make. Let’s run through a few of the most common occasions where a dress shoe will work for your wardrobe. Hint – it’s almost any occasion.

Formal

Your more formal dress shoe should be built for style and look, not necessarily comfort. They’re typically shiny and polishable. Formal style dress shoes can also come in brogue, which is a pattern of perforations or ribboning around the shoe. All in all, dress shoes for a formal occasion will be more plain-looking that an office of a smart-casual shoe. They will be more muted to convey the importance of the event over the “loudness” of the outfit.

Office & Career

A step down the casual scale, the office or career dress shoe is also built for looks, but will also have some extra padding to provide all-day comfort. They may come polishable but generally come with a matte finish, reducing the upkeep time. Where formal shoes typically only work with very formal dress, office, or career dress shoes work with a variety of different pants and dress shirts, from button-downs, ties, and dress pants to chinos and polos. Generally, they’re plain on the surface – you won’t find many brogues here.

Formal Casual or Smart Casual

One more rung down the ladder, and we arrive at the official or smart casual dress shoe. These tend to have thicker soles for pavement walking and may even have athletic shoe soles. Brogue is often employed here as a stylistic choice, and there tends to be a much more extensive color selection beyond your standard browns and blacks. Comfortable insoles, waterproofing, and slip resistance are hallmarks of this type of dress shoe.

4. Price

The price for a pair of men’s dress shoes can range from about $50 to well over $400. There are a whole host of factors at work here, from material to brand name. Our recommendation is to correlate the price with its use. If you’ll be wearing shoes often and spending a lot of time on your feet, it’s better to invest in a more expensive pair of shoes. If you’re looking for a very comfortable, fashionable dress shoe that will keep a long time, you should expect to pay more.

If you’re attending a particular event and will likely only wear the shoes once or twice, consider getting a cheaper shoe. A vital tip, regardless; keep an eye out for the types of materials and look less at the brand name.

5. Lacing

Depending on the style, your dress shoes may have laces or not. A monk shoe, for example, has no laces because it has a single or double buckle across the front. The loafer also has no laces (or may have fake laces that do not function) because there are sized to allow your foot to fit firmly with no laces. Oxford has laces, and the styling and color choice of them is a meaningful way to make your dress shoes unique.

Beyond the style, consider if you would rather not bend over to tie or retie your shoes.

6. Unique Features

Dress shoes come with as many unique features as any other article of clothing, which can add to style and comfort. There are a few key features that add some key elements depending on function. For example, extra padding may be preferable if you’ll be on your feet frequently. Leather outsoles or waterproofing are also very important for those who may find themselves in the elements.

Slip resistance and non-marking soles are essential for both restaurant and bar workers or those who work on wood floors. Diabetic approved shoes are also made to lessen pressure on both the front and back of the shoes.

7. Brogue

Brogue comes from the Gaelic and Scottish word for “shoe” and is a style of perforation and serration along with the leather uppers of shoes (source). Brogue is nothing more than decorative. More formal dress shoes tend to contain less brogue. There are four main designs of brogues:

Semi: One of the most subtle, the decorative patterns are located only on the toe cap of the shoe and along the seams.

Full: Essentially, a Wingtip shoe, the full brogue, is a bold choice and is generally not paired with jeans. The design begins at the toe and this along the entire side of the shoe.

Quarter: The most subtle, the quarter brogue, is only located on the seam of the toe cap.

Longwing: Similar to the Wingtip, the longwing brogue pattern extends down the entire side of the shoe and around to the back. The W-shape of the brogue can distinguish it at the toe, and it’s commonly used in Derby-style shoes.

8. Toe Shape

The toe of the shoe is the most recognizable part, so it’s essential to get it right for your style and the occasion. There are five types of toe design. First is the plain. No adornment, nothing fancy; this style can be worn both formally or casually. Second, is the split toe. Simple enough, the split toe adds a single vertical stitch in the middle of the shoe. The third is the cap-toe shoe, which adds an extra visible layer on top of the shoe with a visible seam. Cap-toes tend to scale with color in regards to formal or casual. The darker the shoe, the more formal, the lighter, the more casual. Cap-toes feature just enough style for any man and occasion.

Wingtips are almost the exact opposite of the first two toe shapes. If you want to add a noticeable flair to your dress shoe, you want wingtips. The name derives from the wing-shaped embroidered look of the toes. Dating from the 1920’s wingtips come in a variety of colors, and recently, two-tone has come back into style.

Finally, the medallion shoe is the punch-designed leather on top of the shoe and is frequently used in cowboys boots or more casual shoes.

9. Heel Height

Don’t get too uppity about the terminology here. The fact is, most men’s dress shoes have a short heel, and its size can be beneficial if you’re a man of shorter stature.

Typically, most men’s dress shoes have a shallow heel height. Dress boots, however, may have a more aggressive heel and can offer a cowboy boot style lift. If you’re particular about your shoe height, you can even consider elevator shoes. Go with the heel height with which you’re most comfortable.

The Best Dress Shoes for Men of 2019 Reviewed

Now that you know all about the factors to keep in mind when looking for a men’s shoe, we’ll run down the best of the best. As always, think carefully about how you’ll be wearing your shoes and how frequently you’ll be wearing it.

1. Allen Edmonds Wing Tip Dress Shoes

Best Dress Shoes for Men Overall

It’s hard to narrow down men’s shoes to the best shoe overall, but the Allen Edmonds McAllister Wingtip makes things interesting. Available in a variety of different shades of brown and black, this shoe is 100% leather and made in the USA. It offers a beautiful brogue around the toe and heel and six eyelet lacing. The Wingtip is available in eight different widths, and the price range does depend on that width size; it lands on the higher end of our range.

Built on the original 360 Goodyear Bench Welt, these shoes can be worn with a variety of outfits, including khakis and high-quality denim.

Pros

  • 100% Leather, made in the USA
  • Attractive brogue design, subtle yet exciting
  • Available in many colors

Cons

  • Not right for more formal occasions
  • Difficult to shine

What You Need To Know

The all-around best shoe on the list, the Allen Edmonds McAllister Wingtip offers style and great selection in color and size.

Read hundreds of other reviews here on Amazon.

2. Charles Tyrwhitt Monk Men’s Dress Shoe

Best Workplace Dress Shoes

Charles Tyrwhitt made their name producing gorgeous men’s shirts and have branched out to provide a whole host of men’s products. The best workplace shoe we found was the Monk Performance Shoe. Don’t balk at the word performance in the dress shoe world. This double buckle shoe is 100% calf leather, providing a beautiful, pliable upper. The sole is made from flexible shock-absorbing rubber and molded foam footbed. It’s also lined with 100% leather and a comfort insole. Charles Tyrwhitt products also come along with a 6- month guarantee and do show up in the upper-middle portion of our price range.

Pros

  • Trainer-style insoles for comfort
  • Stylish full leather outside
  • Great quality guarantee

Cons

  • A bit pricey
  • Only for more casual occasions

What You Need To Know

If comfort mixed with style is a critical element for finding a great dress shoe, the Charles Tyrwhitt Monk Performance shoe needs to be on your shortlist.

Read hundreds of other reviews here.

3. Cole Haan Oxford Dress Shoes

Most Comfortable Dress Shoes

We said the Charles Tyrwhitt was comfortable, but wait until you slide your foot into the Cole Haan Original Grand Wingtip Oxford. Cole Haan has a growing reputation for producing some of the most comfortable soles available in men’s shoes. Available in several different colors, sizes, and widths, this model is true to size and very attractive. Definitely on the cheaper end of the spectrum as well. The athletic shoe style sole makes walking and moving easy while the beautiful full leather upper allows for a nice clean look. The color scheme may not suit all wearers, and this shoe is best worn with chinos or blue jeans.

Pros

  • Exceptionally comfortable
  • Available in a wide variety of sizes and colors
  • The lower end of the price range

Cons

  • Color of the sole may be a turn off for some

What You Need To Know

An absolute must-buy if you’re on a budget and need a casual work shoe, this Cole Haan wingtip provides extreme comfort with a sleek design.

Read hundreds of other reviews here.

4. Red Wing Heritage Oxford Dress Shoes For Men

Casual Dress Shoe

Sometimes you need to dress up your style just a bit, just enough that it takes your outfit to the next level. A great pair of casual dress shoes can do that with ease, and the Red Wing Heritage Weekender Oxford is the best we’ve found. For more than a century, Red Wing has been making work focused boots and shoes that are made in America with the finest materials. Made with that century of experience, the Weekender combines sturdy footwear with something stylish and sleek. The shoe can be resoled and is water, stain, and perspiration resistant. Plus, the free shipping and returns from Huckberry make this a great option.

Pros

  • A classic brand, well made.
  • Available in four colors
  • Free shipping and returns

Cons

  • No width options
  • Limited sizes as of this writing

What You Need To Know

The perfect shoe for weekend tailgates or evenings at the bar, the Weekender combines great heritage with functional dress shoes.

Read hundreds of other reviews here.

5. Ted Baker Oxford Dress Shoes For Men

Best Formal Dress Shoes

There aren’t too many things more masculine than a well-designed, sleek black dress shoe, and the Ted Baker Fharen Cap Toe doesn’t disappoint. Patten shine and textured leather make this 100% leather dress shoe the epitome of class. The very light blue stitching allows for a bit of flare as well. As with all formal dress shoes, you’ll only find this in black, and the middle of the range pricing will ensure you’re keeping your wallet happy as well. The closed flap lacing adds a beautiful finished look, and the synthetic sole provides comfort. The textured upper shoe adds a charming accent.

Pros

  • Accented upper makes for a more stylistic formal shoe
  • True to size and available in many options
  • Blue stitch provides a lovely accent

Cons

  • A bit pricey for a single event wear shoe.
  • It can be challenging to care for.

What You Need To Know

The Fharen Cap To Oxford from Ted Baker London is the quintessential men’s dress shoe; if that’s what you’re looking for, this is the shoe you want.

Read hundreds of other reviews here.

6. Cole Haan Pinch Tassel Men’s Loafer

Best Slip-On Dress Shoes

A good pair of loafers can take a casual look up to the next level or dress down a more formal outfit, like a suit. The Cole Haan Pinch Tassel Loafer is a standard looking tassel loafer that provides comfort and craftsmanship. The stacked heel also provides a bit of lift, excellent for the man that wants to be just a hair taller. Available in both black and an attractive burgundy, these loafers are available in extensive options as well as a variety of sizes. Since their loafers, sizing is important, so be sure to get what works for you. Ranges from inexpensive to middle of the spectrum.

Pros

  • Classic tassel loafer
  • Patent leather does cleaning and cares easy
  • Burgandy color is quite attractive

Cons

  • The classic look may not be right for all
  • In between sized feet may be difficult

What You Need To Know

A perfect pair of men's loafers are almost a necessary addition to your closet, and the Cole Haan Pinch Tassel Loafer is a must-own if you like the classic look.

Read hundreds of other reviews here on Amazon.

7. Clarks Tilden Walking Men’s Dress Shoes

Walking Dress Shoes

Clarks has been making great men’s shoes for more than a century, and that shows in the Tilden Walk Oxford. Made with leather and a fully synthetic sole, these Clarks feature a breathable leather upper that provides a snug but flexible fit. The two elastic side gores provide some much-needed stretch when you’re walking quickly. Available in four colors and a variety of sizes, these Clarks are perfect for the man that needs a smart casual work shoe. Buyers note that the shoe tends to run a bit narrow, so if you find you’re in between sizes, it would be best to go up a size.

Pros

  • Available in many colors
  • Durable sole
  • The lower end of the price range

Cons

  • Runs narrow
  • Cannot be resoled

What You Need To Know

If you’re looking for the perfect everyday shoe for walking to or at work, the Tilden Walk Oxford is an attractive, cost-effective option.

Read hundreds of other reviews here on Amazon.

8. Hush Puppies Venture Men’s Dress Shoe

Diabetic Approved Dress Shoes

Hush Puppies are known for that uber-comfortable shoes, and these Ventures are no different. They have to be if they’re approved for diabetic wearers. At just 12 oz. each, they’re easy to walk in, and the full-grain waterproof leather keeps the elements off your toes. HP uses a patented chemical bond to join the leather upper and the outsole to keep everything together. It also provides strong midfoot support and strikes back gel pad in the heel for extra cushion. A variety of sizes, colors, and widths are available, and they’re very affordable

Pros

  • Wide range of sizes and colors
  • Diabetic approved
  • Full-grain leather for durability

Cons

  • Customers report some leather fading

What You Need To Know

Hush Puppies bring the epitome of comfort to these shoes while maintaining necessities for those living with diabetes.

Read hundreds of other reviews here.

9. Dockers Gordon Leather Oxfords

Best Affordable / Cheap Dress Shoes

Sometimes you don’t want to break the bank for a new pair of shoes. The Dockers Gordon Leather Oxford offers quality footwear for under $100. Available in black or brown, the full-grain leather upper and rubber sole provides a durable shoe and a comfortable ride. The padded collars add an extra bit of comfort, and the cap toe elevates the look. The laces provided here will also keep these shoes firmly on your foot, threaded through reinforced eyelets.

Pros

  • Inexpensive
  • Rubber sole for extra traction
  • Excellent lace construction

Cons

  • Limited colors
  • Cannot be resoled

What You Need To Know

Cheap isn't a bad word with these Docker's – comfortable features and superior construction, make these inexpensive shoes a great option.

Read hundreds of other reviews here.

10. Rockport Oxford Non-Slip Mne’s Dress Shoes

Slip Resistant Dress Shoes

If your job requires that you wear a durable, slip-resistant shoe, it can be hard to find something that looks great but still serves the purpose. Look no further than the Rockport Essential Details Waterproof Plain Tow Oxford. Available in several widths and sizes, these shoes are treated with Rockport’s Hydro-Sheild technology that keeps moisture away from your feet.  Rockport knows that if you’re wearing nonslip shoes, you’re on your feet all day – the uppers are crafted with leather for comfort, and a rubber sole and padded inner provides vital support. Best of all, they look great.

Pros

  • Slip-resistant and waterproof
  • Secure fit with traditional laces
  • Attractive

Cons

  • Only available in black
  • The treatment makes leather appear dusty

What You Need To Know

Slip-resistant shoes that are attractive are tough to find – look no further than these Rockport’s, as long as the black color works for you.

Read hundreds of other reviews here.

How to Care for Your Dress Shoes

how to care for dress shoes

Picking out a great pair of dress shoes is essential, but arguably more important is taking great care of them. Regardless of the material, your shoes are made from (like leather or suede), the following two rules apply. First, cobblers exist for a reason – know when you should get your shoes resoled. A hole in the bottom is a good sign, but when they become excessively worn, consider heading to your local shoe repair. Second, don’t over wear the same pair of shoes. Consider rotating them with other pairs you have in your wardrobe. This will keep each pair looking fresher, longer.

How To Care For Suede Dress Shoes Properly

  1. Use a medium bristle brush to remove or gently lift or loosen surface stains. This will work to get out any stray dirt or errant fibers.
  2. Use a suede eraser to remove marks or any blemishes that remain on the surface. Make sure you test the eraser on an unnoticeable area first, like the inside tongue of the shoe, to ensure it doesn’t leave a mark.
  3. Finally, use a waterproof or protectant suede spray. This helps to create a barrier to prevent marks or stains.

Care For Leather Dress Shoes Properly

There are four significant steps to cleaning and maintaining leather shoes. You don’t always have to clean the shows, but you should consider conditioning and applying protectant frequently.

1. Leather Cleaning

Start with saddle soap or leather cleaner like Lexol to remove any dirt, grime or stains. Soap specifically made for leather conditioning works better than a traditional cleanser. It has the added benefit of preventing cracking or stiffness in the leather. When applying the soap, always work in a circular motion from front to back, then wipe away any excess with a slightly damp cloth.

2. Leather Conditioning

Conditioning the leather adds back the natural moisturizers for the hide and mimics the natural sebum that keeps a hide feeling soft and supple. It can also add a beautiful, moderate shine. You can apply to the condition using an old sock or shirt. Again in a circular motion, ensure that your shoes are completely covered – follow with a clean cloth, then a horsehair brush.

3. Leather Protectant

Protectant is typically a combo of beeswax and lanolin. You should think of it more as applying a water-resistant substance rather than fully waterproof; water can still get in around tongue, eyelets, and welt. This is great for dress shoes during those snowy, wet winter months.

4. Shoe Tree

Possibly the most crucial step, a good shoe tree, prevents rot of a dress shoe by removing moisture within it. It helps retain the structure of the shoe over several years and is especially crucial with shoes you don’t wear frequently.

5 Tips on How to Wear Dress Shoes Perfectly

Grabbed your new dress shoes but need some tips on how to wear them with your wardrobe? Read onward.

1. Match With Your Belt

Brown shoes, brown belt. Easy as that. Remember, it doesn’t have to be an exact match. A lighter shade of brown can bring a beautiful pop into the middle of your outfit. However, you should try to get the general essence of the color.

2. Know When To Get A Polish

If we’re talking leather, get them polished regularly. This feeds into an old school mentality, which can be fun, but it is essential if you want to keep your shoes for an extended period.

3. Shoehorn Prevents Overstretching Leather

Not only does a shoehorn help you get your foot in the shoe, but it also prevents you from wiggling and turning your foot and stretching out an inherently rigid material. It’s better for the overall health of the shoe.

4. Get Them Resoled When Necessary

A local cobbler will be your friend here – if you’re not sure, ask. A new outsole varies depending on supplies, but it will typically set you back less than $75. It’s an insignificant investment if you got a nice pair, and the rest of the shoe is in good shape.

5. Know What To Wear & When

Super formal shoes shouldn’t be worn as weekend wear. You’ll find very quickly that they’re uncomfortable and falling apart. Office shoes should be worn with dress pants or khakis, while casual shoes can be worn with dark denim or a chino.

Common Questions Men Had About Dress Shoes

How long does it take shoes to get resoled?

This is highly dependent on the cobbler’s schedule, but generally, about a week.

Is it worth getting dress shoes repaired?

Absolutely if your shoes come from a decent brand and are high-quality leather, like full or top grain. Getting your shoes repaired can make them last significantly longer and provide you with a better walking experience. On average, a shoe can be resoled two to three times.

How much does a good pair of dress shoes cost?

Hard to say, but you can easily spend several hundred dollars. We find that most quality shoes rest somewhere around the $200 mark.

What dress shoes are in style?

Monk-Strap, Brogue details (found on derby and oxford dress shoes) and some dress boots, like Chelsea boots, are all in style at the moment. Your traditional Oxford dress shoe will likely never go out of style.

Dress Shoes vs. Dress Boots

Dress Shoes

Dress shoes come in many different varieties (see more above).

  • Oxford: Your go-to dress shoe for virtually all occasions, the only real difference between these two types of shoe are the laces. Derby shoes feature an open flap, while the Oxford has a closed flap over the laces.
  • Loafers: Always good to have in the closet, a good pair of loafers can build a sense of style without the need to tie any laces
  • Single & Double Monk: Monk shoes are designed with a single or double buckle closure that comes over the top of the shoe. They are somewhere in the middle of formal and casual shoes.

Dress Boots

Dress boots come in equally as many varieties, and figuring out when and where to wear each type can be a challenge, especially if you’re a new boot wearer.

  • Chukka (Desert Boots)
    • More of a smart casual or casual boot that is to be worn in relaxed office and weekend wear
    • Chunkier
    • Worn with dark denim or chinos
    • Has laces
  • Chelsea
    • More sophisticated boot when compared to a chukka boot
    • Usually zip or elastic closure
    • Ankle length and slightly rounded toes
    • No laces
  • Brogue Boots
    • Has the classic brogue finish and design
    • Cut at the ankle height
    • Works for both chinos or dark denim
    • More of a bridge boot between casual and office setting
  • Derby Boots
    • Like derby dress shoes – just cut higher
    • Typically leather
    • Pair with dress pants and blazer
  • Oxford Boots
    • Again, like a derby shoe – just cut higher
    • More formal and slightly different lace closure compared to derby
    • Paired with dress pants

Our Criteria for Choosing the Best Dress Shoes

We looked closely at a variety of aspects that you can see in our buying considerations. These included material, price, laces, occasion, durability, and comfort.

We think we’ve found a dress shoe that nearly every man should have in their closet.

About The Author

Shawn Burns

Shawn is the founder and senior editor at Tools of Men, the leading style and grooming source trusted by men in 187 countries. He started this site with the goal of teaching men proper grooming habits and sensible style. He is an expert in all things men's grooming related. His work has been mentioned on countless sites including The Wall Street Journal, NBC, AskMen, Vice, WikiHow, and the New York Times.

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