1. Allen Edmonds Men’s Larchmont Lace-Up – The Best Wingtip Men’s Shoes

What better way to start off the list than with an American-made classic from a company that has nothing but the utmost respect for its customers as well as its employees? Allen Edmonds have been in the shoe making business for almost 100 years now, and the Larchmont is the foremost of their men’s wingtip shoes, winning customers over with style and quality.

You’d be hard pressed to find a shoe made with better materials. Everything from its finely-decorated upper made from supple leather all the way to the ergonomic footbed tells of the shoe’s distinction and visible durability. The motif done by holes punched through the leather certainly makes them stand out, and even though it won’t fit in with a more serious business look, they’re the perfect solution when you want to appear a bit more casual, but still well-dressed.

Wearing the Larchmont has been nothing but a pleasure. They fit very well, allow you to move around in them with ease, and, best to all, they look amazing! If you’ve been looking for an upscale shoe you won’t regret spending every penny on, then look no further than the Larchmont.

2. Allen Edmonds Men’s McAllister Wing Tip – Brown Wingtip Shoes for the Distinguished Gentleman

Another one of Allan Edmonds’ instantly recognizable wingtip models, the McAllister is a dress shoe that will last you for years, and whose timeless design is sure to stay relevant however long you plan on wearing yours.

As soon as you take them out of their box for the first time, the unmistakable smell of leather will tell you how much value Allan Edmonds place on the materials they use. The stitching throughout the shoes holds up very well, as does the general construction of their cork filling and insole. When wearing these, you’ll notice that your feet can breathe easily while being completely protected from the elements.

The color selection with this model is spot on. While brown wingtip shoes are still the norm, the McAllister pulls rich burgundy and traditional black off with the same class.

Once you settle on a nice pair though, you might start coming up with excuses just to wear them almost all the time. Just combine them with a fine jacket and your favorite pair of slacks, and you’ll be dressed for all but the most formal of occasions.

3. Asher Green Men’s Two Tone Brown Leather Wingtip Oxford – The Best Two Toned Wingtip Shoes

Limiting yourself to just one shoe color can be boring. More tones give you the opportunity to experiment with different outfits and combination, but more often than not two toned shoes just don’t look as dignified. Asher Green were apparently thinking the same thing and have come up with two tone wingtip shoes that will enhance your style rather than take away from it.

A little note about two toned wingtips is that they’re also referred to as spectator shoes or co-respondent shoes. This style of shoe dates from the nineteenth century but were popular in the 1920s and 1930s.

These Asher Green shoes offer a surprising variety of combinations to choose from, but the ombre brown and cognac one steals the show. It isn’t too out there, the two tones complement each other very nicely without creating a pronounced contrast, and the subtle difference between them will break the monotony without making the shoes much more casual.

From a quality standpoint, Asher Green have done a good job selecting the leather and synthetics the shoes are made from, as well as with the stitching, laces and blocked heel. Considering that the shoes are inexpensive, the craftsmanship put into them is excellent.

Those of you who aren’t afraid to take their dresswear a step further will find that Asher Green have come up with a convincing recipe for great looking two tone shoes. At this price point, getting a pair is very tempting, so why not pull the trigger and grow your collection with something truly special?

4. Jean Yves Two Tone Wing Tip – Black and White Wingtip Shoes for the Important Days in Your Life

To be sure, Asher Green makes a fine pair of shoes, but you wouldn’t exactly consider wearing them to a formal event like a prom or a wedding. If you love the style but need something a bit less casual, don’t despair, because Jean Yves have taken it upon themselves to make a similar shoe and spruce it up so that you can pick up your prom date or walk down the aisle in a pair with confidence.

Jean Yves enjoy a huge success with their various types of formal wear, and there’s no room for doubt that they applied the same level of care and professionalism in designing these men’s black and white wingtip shoes. The ultimate contrast of black and white is done tastefully along with the pattern of “holes” on the toe cap. The shoes look harmonious as a whole, and are very comfortable to wear too.

These shoes are an affordable, elegant and refreshing solution to the challenge of picking the right shoe for the moments in life you’ll remember forever. Black and white is a striking combination on its own, and this shoe is what can be achieved when it is used with skill and an eye for the beautiful.

5. Magnanni Men’s Sergio Oxford – Wingtip Dress Shoes Inspired by European Elegance

With the two toned models out of the way, it is time to make a brief trip across the Atlantic and take a closer look at what the Spanish have to say when it comes to wingtip dresse shoes. If we take the Sergio by Magnanni as the standard, the answer to that question becomes “quite a lot”!

Their most attractive feature are the elaborate decorations made by punching holes through the upper, more so than with most American models. That coupled with a slight tapering of the toe gives them that gentle touch of European influence that makes these shoes stand out from the crowd.

Other than standard but nevertheless interesting black and brown tones, the Sergio is also available in a mix of navy blue upper and brown sole. This isn’t exactly traditional, but can make a great first impression if combined with the right outfit.

The Sergio is a shoe you’ll wear with a sense of sophistication that only comes from products whose price tag reflects superb craftsmanship and quality, not just the brand name. Their exotic influences and overall look are sure to stir up a conversation or two, giving you a chance not just to look good, but to impress with your fine taste in dresswear too.

6. Johnston & Murphy Men’s Greenwich Oxford – The Black Wingtip Shoes that Put a Spring in Your Step

As I’ve mentioned a couple of times already, some of these wingtips didn’t feel right the first time and had to be broken in. This is definitely not the case with the Greenwich Oxfords from Johnston & Murphy though – expect a more or less perfect fit the moment you put these on!

Once you take a closer look at them, it becomes clear why. Everything about these shoes has been made to ensure that your feet fit snugly, have room to breathe and are given optimum support. Their cushioning system softens the blows prolonged walking deals to your feet, leaving you less tired and better able to mingle or tackle a challenging problem at work.

When style is concerned, the ornaments have been toned down to a minimum. They come in a couple of shades of brown as well as two lovely shades of black. If you choose that color you can go to work in them without feeling under-dressed. Actually, these might be the best black wingtip shoes for a business environment I’ve reviewed so far.

The Greenwich Oxford is one of the most comfortable and well-fitting men’s wingtip shoes there is. Coupled with their versatility and simple yet impressive appearance, this makes for a very convincing argument to treat yourself to a pair.

7. Florsheim Men’s Montinaro Wingtip Oxford – Men’s Brown Wingtip Dress Shoes for Almost Any Occasion

Excellent customer service, quality and inspired shoe design have been synonymous with the name Florsheim since the end of the 19th century. Even though they’ve suffered a few hiccups during their proud history, the Florsheim family are at the top of their game again, and the Montinaro is the best argument I can think of to convince you of this.

These men’s brown wingtip dress shoes show off all of the qualities that make this type of shoe so popular. First of all, there’s the outstanding leather they’re made out of. It is neither too hard nor too shiny, adapting itself well to one’s foot and leaving a somewhat conservative yet definitely classy impression. The sole is made from synthetic materials but is durable enough to keep up even with frequent use.

Their design isn’t too flashy, but you can tell that a lot of thought has been put into the upper’s pattern layout, the lacing and the look of the heelcap. Subtle details like that can tell you a lot about the manufacturer’s vision for the shoe, and Florsheim’s speaks of quiet evenings with good friends at exclusive uptown restaurants.

In the end, the Montinaro is a wingtip you should seriously consider. It is certainly casual at heart, but that isn’t stopping it from projecting both confidence and a sleek, individualistic style you’ll fall in love with instantly.

8. Ted Baker Men’s Apren Oxford – The Best Woolen Casual Wingtip Shoes

So far all of the shoes I’ve talked about were either made from high grade leather, or were trying to imitate a leathery appearance. Ted Baker have never shied away from putting an unusual twist on designer clothing and accessories, and have come up with a woolen alternative that looks really good and feels even more comfortable.

Naturally, the most interesting part of these causal wingtip shoes is their upper. While its design is similar to other shoes of its kind, the upper isn’t punctured with holes. Rather, the wool itself and the stitching that holds it together are the main sources of decoration. This is especially true for the wool’s natural grainy pattern that makes every pair unique.

The rubber sole on the other hand does a fine job of protecting your feet from damp and cold. Together with the cushioned insole they form a comfortable base to walk on.

Having to be more careful with your shoes is a small price to pay if you ask me, considering how well this pair looks and feels. Whether you’re fashion-conscious or just want a nice pair of shoes you can relax in, Ted Baker have made it possible in a one-of-a-kind way.

9. Stacy Adams Men’s Stockwell Wingtip Oxford – The Best Stacy Adams Wingtip Shoes

Sometimes you just want to wear good looking shoes that won’t cost you a fortune. Usually there’s a compromise – either you’re sacrificing the build quality, a perfect fit or stylishness in order to lower that price to something within your budget. Lucky for you that Stacy Adams have designed a pair of wingtips that don’t lose out much on any of these while still being very reasonably priced.

Their exterior is in line with what you’d expect from a casual dress shoe, but without some of the fancier decorative elements, we’ve seen with other models. This is actually a good thing since it means you’ll be able to wear them to work and not be out of place, provided the dress code isn’t too stiff.

The shoes feel and look much more expensive than they actually are. The subdued color tones, the perfect amount of sheen and synthetic yet sturdy soles which have an excellent grip even on slippery surfaces all point to the conclusion that Stacy Adams wingtip shoes are made to last and be admired.

The Stockwell is definitely one of my favorite shoes in the guide. It offers an amazing cost to benefit ratio, and even if you buy a pair just because you’re strapped for cash or in a pinch, there’s a good chance you’ll stick with them for a long time once you try them on.

10. Cole Haan Men’s Cambridge Wingtip Oxford Shoe – Simple Wingtip Oxford Shoes that Impress

Virtually every company I’ve mentioned so far has a long history of being in the shoe business and producing recognizable footwear, and it is no different with Cole Haan, the New York-based manufacturer that has been making signature men’s footwear since the roaring twenties.

Their current generation of wingtip Oxford shoes continues the trend, offering a look that is simple enough to be taken seriously, but still well within wingtip territory suitable for cocktail parties and an upscale night out on the town.

Holes have been placed only at the base of the heel cap and lacing area. It is enough to clearly identify their British ancestry, but it is also in line with the distinct American influences Cole Haan are respected for. The sole is made from a combination of leather and rubber, and along with the heel it turns the shoes into subtle platforms, giving you that extra half-inch to help you stand out.

All in all, Cole Haan have managed to do almost everything right with these shoes – they aren’t too expensive, can easily be worn to work first and a party after that, and, most importantly, I enjoyed wearing them. There’s a very good chance that you will too.