In this article, Courtney Ryan ranks some of the most popular men's shoes in a tier list, sharing her expert opinion on style, versatility, and her personal preferences.

Table of Contents

• Intro and Criteria
• Penny Loafer
• Tassel Loafer
• White Sneaker
• Cowboy Boot
• Oxford Dress Shoe
• All Black Sneaker
• Chelsea Boot
• Chukka Boot
• Double Monk Strap Dress Shoe
• Square Toe Dress Shoe
• Derby Dress Shoe
• Brogue
• Chuck Taylor
• Jordans
• Vans
• Service Boot
• Timberland
• Hey Dudes
• Crocs
• Dress Sneaker
• Driving Loafer
• Boat Shoe
• Conclusion

Intro and Criteria

Welcome to this exciting tier list ranking of men's shoes. Before we dive into the rankings, it's essential to understand the criteria used for evaluation. The three key factors influencing the rankings are style, versatility, and the expert opinion of a fashion professional.

Style

• Timeless taste
• Quality and longevity
• Cost per wear

Style is evaluated based on its timeless appeal, quality, and cost-effectiveness over time.

Versatility

• Functionality
• Adaptability
• Style flexibility

Versatility considers the shoe's ability to serve its intended purpose, adapt to various styles, and offer functional flexibility.

Expert Opinion

The rankings are also influenced by the expert opinion of a fashion professional with a bachelor's degree in fashion and a decade of experience in the industry.

Penny Loafer

Let's take a closer look at the iconic penny loafer and see how it fares based on the established criteria.

Style and Versatility

The penny loafer scores high in both style and versatility. Its timeless appeal, coupled with its ability to be dressed up or down, makes it a versatile and stylish choice for various occasions.

Expert Opinion

The expert opinion also aligns with the high scores for the penny loafer, emphasizing its widespread appeal and adaptability to different fashion preferences.

Tassel Loafer

The tassel loafer, while less formal than the penny loafer, lacks the same level of versatility. It's a niche style that may not work for everyone, lacking the widespread appeal and adaptability of the penny loafer. Consider it as an addition for added variation if you frequently wear penny loafers. It falls into the B or C tier due to its limited versatility compared to the penny loafer.

White Sneaker

The white sneaker is a favorite for its exceptional versatility. Its ability to pair with various outfits makes it a wardrobe essential. Despite the challenge of keeping them clean, white sneakers offer unparalleled adaptability. They are a must-have for anyone looking for a versatile and stylish sneaker option.

Cowboy Boot

The cowboy boot holds a unique and irreplaceable position in the world of footwear. Its distinct Western style sets it apart, making it a standout choice for those embracing a more casual and rugged aesthetic. While not my personal top pick, cowboy boots are undeniably iconic, offering timeless appeal and versatility across various fashion preferences and settings. Their adaptability to both casual and more polished outfits, along with the option for steel-toe variations, makes them a solid choice for a range of occasions. Therefore, I rank the cowboy boot in the B tier, acknowledging its enduring popularity and style impact.

Oxford Dress Shoe

The Oxford dress shoe, a timeless and classic staple, continues to maintain its position as a favored choice for formal and semi-formal occasions. Its versatility and adaptability to different dress codes make it a reliable option for a wide range of events. While it doesn't quite reach the highest tier due to considerations about frequency of formal events, it still earns a solid place in the A tier. With its potential to move up to the S tier based on further evaluations, the Oxford dress shoe remains a strong contender for men seeking a sophisticated and versatile footwear option.

All Black Sneaker

The all black sneaker holds a special place in many people's memories, often associated with work uniforms and specific dress codes. Its lack of style elements makes it a challenging choice for fashion-conscious individuals. While it may suit those with a predominantly muted wardrobe, the stark contrast it creates with other outfit colors can be harsh. Additionally, the versatility of the all black sneaker is limited, with its suitability mainly restricted to specific monochromatic ensembles. Due to its lack of timeless appeal and limited versatility, the all black sneaker is placed in the D tier.

Chelsea Boot

The Chelsea boot presents an intriguing dichotomy, with variations in suede and smooth leather offering distinct aesthetic qualities. The smooth leather Chelsea boot has the potential to be dressed up, adding a touch of sophistication to certain outfits. Conversely, the suede Chelsea boot is more suited to casual ensembles, such as denim and flannel combinations. However, the Chelsea boot, as a category, has garnered mixed opinions and may not be the first choice for either dressy or casual occasions when compared to other boot styles. The smooth leather Chelsea boot earns a place in the B tier due to its dress-up potential, despite not being the top preference. Conversely, the suede Chelsea boot is placed in the C tier, reflecting its limited versatility and its unfortunate association with being a fashion meme.

Chukka Boot

The Chukka boot, while featuring a distinct silhouette, may not be the top pick for many due to its less flattering appearance compared to other boot styles like the Chelsea or service boots. The suede material limits its versatility, making it challenging to dress up for various occasions. Additionally, the aging factor of this style may not be as favorable as other boot options, impacting its long-term appeal and style. Considering these factors, the Chukka boot falls into the D tier for its limited style and versatility, making it a less preferred choice compared to other boot styles.

Double Monk Strap Dress Shoe

The double monk strap dress shoe, while a sartorially striking choice, may not offer the same level of versatility as the Oxford or derby shoes. Its appeal leans more towards those who already have a diverse collection of dress shoes and seek variation in their wardrobe. While timeless and visually appealing, the double monk strap dress shoe may not cater to a wide range of men's fashion preferences and dressing habits. This places it in the middle of the road, earning a fair position in the C tier. While it has the potential to teeter between the B and C tier, its limited versatility in comparison to other dress shoe types influences its ranking in the tier list.

Square Toe Dress Shoe

The square toe dress shoe, often associated with early 2000s fashion, lacks the timeless appeal and visual silhouette desired in formal footwear. The blunt, harsh cut-off of the square toe fails to elongate the leg and creates a visually unappealing shape. While some silhouettes may be more flattering than others, the overall style impact of square toe dress shoes is limited, earning it a low ranking in the tier list.

Derby Dress Shoe

The Derby dress shoe is an underrated option that offers versatility and functionality, especially with the availability of different sole options such as a rubber sole. This feature makes it a practical choice for individuals living in areas with challenging weather conditions. The Derby's ability to be dressed up or down, combined with its functionality, earns it a solid place in the A tier.

Brogue

Brogue refers to a pattern of perforations found on various types of footwear, not just dress shoes. Originally designed for practical purposes, such as allowing water to drain out of the shoe, brogues now serve more as a decorative feature in modern footwear. While less common, the history and unique aesthetic of brogues make them an interesting addition to any shoe collection. Despite their intended versatility, brogues are now primarily used as a decorative element, adding personality and flair to an outfit.

Chuck Taylor

Chuck Taylor shoes, known for their iconic status, offer a distinct style that appeals to many individuals. While versatile in their own right, they may not offer the same level of adaptability as a basic white sneaker. The specific style of Chuck Taylor shoes may not suit every fashion preference and can create a less refined silhouette compared to other sneaker options. Despite their limitations, the diverse range of styles and colors available for Chuck Taylor shoes caters to a wide demographic, contributing to their enduring popularity and appeal. Placing them in the B tier acknowledges their iconic status and unique appeal, while recognizing the preference for other versatile sneaker options.

Jordans

Jordans are a controversial choice, with varying styles that can range from hideous to fantastic depending on the right guy, style, and outfit. Some variations may be considered iconic, while others could be seen as a monstrosity. Due to the wide range of styles and the difficulty in categorizing them, Jordans are placed in the C tier, bordering on D tier due to their limited versatility and appeal in certain fashion contexts.

Vans

Vans are known for their association with skate style and are best suited for individuals who embrace this specific fashion aesthetic. However, they may not be as versatile or suitable for a wide range of styles. While iconic in black and white, they can create a peculiar silhouette and may not complement every outfit. Due to their limited versatility and overdone presence in the market, Vans are placed in the C tier, bordering on D tier, reflecting their neutral standing in terms of style and versatility.

Service Boot

The service boot is a versatile and stylish choice for men's footwear. It offers a wide range of options to cater to various fashion preferences, from polished and put-together looks to casual and rugged styles. With its adaptability to different dressing aesthetics, the service boot stands out as a versatile and timeless option. Additionally, its ability to withstand challenging weather conditions, with options for rubber soles suitable for various environments, adds to its appeal and practicality. The service boot's versatility and style make it a top contender for any man's shoe collection, earning it high ratings in both categories.

Timberland

The Timberland boot, once popular in the early 2000s or '90s, has lost some of its appeal in recent times. The bulky and clunky appearance of Timberland boots may not create the most flattering silhouette, impacting their overall style rating. While they may have been trendy in the past, their current aesthetic may not align with modern fashion preferences. However, individual opinions on Timberland boots may vary, and some may still find them appealing for specific fashion contexts or nostalgic reasons.

Hey Dudes

Hey dudes have sparked a fair amount of controversy, but it's no secret that they are a highly polarizing choice in the world of footwear. While they may initially appear to offer comfort, the reality is a bit different. Despite their initial appeal, the long-term comfort and support they provide fall short, making them a questionable investment for both your feet and your wallet. Additionally, their style and versatility leave much to be desired, leading to a unanimous agreement on their lackluster appeal. It's safe to say that hey dudes occupy a category of their own, characterized by their questionable comfort and style attributes, warranting a distinct classification in the tier list.

Crocs

Crocs, often at the center of style debates, elicit strong opinions due to their distinctive appearance and functionality. While they may not be synonymous with timeless style, they do serve specific practical purposes in certain scenarios. Their unique design, equipped with drainage holes, makes them suitable for activities involving water, ensuring foot protection in various recreational settings. Although they may not win any style awards, their specialized utility in specific situations sets them apart from the complete dismissal received by hey dudes. Consequently, Crocs, while not excelling in style or versatility, secure a place in the tier list that acknowledges their distinct functional value.

Dress Sneaker

The dress sneaker attempts to blend the features of a dress shoe and a sneaker but falls short in effectively serving the purpose of either. It's not suitable for pairing with a suit and lacks the functionality of a typical sneaker. While it may be a comfortable option for a walk from home to the office, its versatility is limited. In most cases, opting for a separate dress shoe and sneaker would be more practical. The dress sneaker is placed in the D tier, signifying its subpar performance and limited functionality compared to dedicated dress shoes and sneakers.

Driving Loafer

Driving loafers are a casual style that can sometimes resemble house slippers, especially when made of suede. While they can look great, they may not offer the versatility and ability to be dressed up as much as other loafer styles. For those seeking versatility, a driving loafer may not be the top choice.

Boat Shoe

Boat shoes were originally designed for grip on slippery decks in wet conditions, with non-marking soles to preserve the boat's aesthetic. However, their reputation has been influenced by their widespread use beyond boating contexts. While some still wear them for their intended purpose, the traditional penny loafer offers a more versatile and aesthetically pleasing alternative for various occasions.

Conclusion

While the tier list ranking of men's shoes is a general and overarching evaluation, it's essential to acknowledge the variations and nuances present in different shoe styles and brands. Specific shoes from particular brands can significantly impact individual preferences and rankings. However, in a broader context, the tier list provides a comprehensive overview of the most versatile and timeless footwear options for men.

Considering the intended purpose of each shoe and its adaptability beyond that purpose, the tier list emphasizes the importance of versatility and style impact. The top-ranked shoes, including the penny loafer, white sneaker, Oxford dress shoe, and service boot, are identified as the most versatile and timeless choices, catering to a wide range of men's fashion preferences and lifestyles.

Personal style and lifestyle play a crucial role in determining the most suitable footwear options for individuals. While this tier list offers a valuable perspective, it's important for individuals to consider their unique preferences and needs when selecting the ideal shoes for their wardrobe. Your personal style and lifestyle should ultimately guide your footwear choices, ensuring that you invest in shoes that align with your individual fashion sensibilities and practical requirements.