BY STEVEN MAY 28, 2023
BY STEVEN MAY 28, 2023
BY STEVEN MAY 28, 2023
BY STEVEN MAY 28, 2023
BY STEVEN MAY 28, 2023
In the ever-evolving world of men’s fashion, one constant remains – the need for stylish and versatile shoes at an affordable price. But what to buy? And how much to spend? From Oxford style to Monkstraps, the options can be confusing. Fortunately, there are stylish, affordable answers for any budget. And that is why I am here! This article will serve as a guide to dress shoe styles and options. The well-chosen, comfortable pair of shoes can make all the difference, whether heading to a high-stakes business meeting, attending a formal event, or simply out for a casual dinner. Does this mean a man’s wardrobe requires dozens of shoe colors and unique dress shoes for special occasions? Absolutely not. Even as seasons change, our shoes and boots should flow effortlessly from one outfit to the next. I will quickly break down different formal and casual styles and then detail how to make the most efficient and fashion-permanent shoe and boot selections with direct links to my recommendations.
Monkstraps For Any Occasion – Shop on Amazon Prime
Building an impressive shoe collection without depleting your savings is a balancing act. The trick is to invest smartly in a handful of versatile, high quality footwear that suits various settings. Instead of stockpiling for every conceivable occasion, look for flexibility in style and color. Pinpoint those with the flexibility to adapt to multiple circumstances. This means less formal styles if you are looking to save. Brown shoes or boots, as a rule, pair better with different outfits. For instance, a soft nubuck leather pair of “Derby” style shoes can slide comfortably into your formal and casual outfits. These are my favorites from Johnston and Murphy. Nubuck dress shoes are versatile and can go from a business meeting to a casual dinner outing. These are my go-to travel shoes. They are durable and easy to maintain. From jeans to slacks, you can't go wrong with a rich, brown, nubuck shoe.
Johnston & Murphy Men's Upton Plain Toe Dark Brown Nubuck
$158.95
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It’s important to understand that quality outweighs quantity regarding men’s footwear. Well-crafted and durable shoes can serve you for years, turning them from a purchase into an investment. Always start with comfort if you need a pair of dress shoes for work. Then, ensure it is durable, versatile, and easy to maintain. Rather than amassing a hoard of inexpensive, low-quality shoes that will quickly wear out, focus on acquiring a few select fashionable and durable pairs.
The key to this cost-effective strategy is remembering that the right shoes can make a statement, no matter the occasion. Therefore, by choosing versatile footwear, you can ensure that your shoe game is always on point, whether stepping into a business meeting, attending a formal event, or heading out for a casual evening. This approach not only ensures you always look stylish, but it also allows you to maximize your fashion budget.
The difference between “Oxford” and “Derby” style dress shoes is subtle. But it can be important. The difference is in the lacing system; most shoes referred to as “Oxfords” are actually “Derbies.” Oxford dress shoes have the eyelet tabs stitched underneath the vamp, while Derby dress shoes have the eyelet tabs stitched on top of the vamp. The Oxford shoe is considered a bit more formal, yet both Oxfords and Derbies will offer style variations such as wingtips or Cap Toe dress shoes.
NOTE: Most dress shoes described as “Oxford” are derbies because the eyelet feature is overlooked. Most people don’t notice, and no one cares enough to emphasize the distinction.
Below are a few of favorites. Amberjack offers incredibly comfortable and stylish hybrid dress shoes. My first and favorite pair are the Chesnut “Cap Toe” shoes. The Rockports can go with anything and are a great price. If you want to punch up your shoe closet and like wearing blue and light gray, grab these Clarks Tan “Captoe” dress shoes.
This is the most addictive shoe money can buy. Amberjack blends comfort science with sleek style. This is the only shoe you need when you travel. The Cap Toe is a versatile option for slacks, chinos, or jeans. Take Business Casual to Business Bad Ass!
Extremely comfortable and versatile. If you have to look sharp and walk/stand often, these are a killer deal!
This is a gorgeous tan, "Cap Toe" dress shoe. This might be the best value for a Cap Toe Oxford on Amazon. These are versatile, comfortable dress shoes. Also, NOT technically an "Oxford" as link will describe.
Nothing beats the classic appeal of a sharp, shined-up pair of black dress shoes for more traditional business or dressy occasions. This Upton Plain Toe from Johnston & Murphy it is extremely comfortable. it goes with any grey, blue, or black/charcoal suit and most of my jeans.
It's a nice take on the "black dress shoe." Johnston and Murphy is a hot brand right now, and these hybrids are a great start to any capsule wardrobe. Versatile and unique!
Need a deal on a more formal look in a true Oxford-style dress shoe? These are an excellent choice from Bruno Marc.
Do you need something a bit more "dressy" for that black/navy/grey suit? This is a steal in the classic black captoe oxford.
If you want versatility but something in a unique color profile, try “Chilli.” These Chilli color dress shoe hybrids from Allen Edmonds are always a hit. The color is dark enough for Navy and Charcoal slacks, but you can also pair these with other shades of blue. It's Allen Edmonds, so yeah, they are a bit pricey. But these are the highest quality shoes I own. And they have hybrid rubber soles, so they save my legs and back when I stand or walk often.
Worth The Investment
Allen Edmonds Carson
$350.00
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At a better price point, I have enjoyed these Cole Haan tan wingtips for over a year.
Comfortable and stylish. I used my photo because they are a shade lighter than the Amazon photo indicates. Which I love, with mid-blue and lighter blue suits and slacks
The loafer dress shoe is an essential for business casual options. However, the grain of leather and style of a loafer can move into a more formal category. For many, their first dress shoe is a quality black loafer. In my estimation, Cole Haan offers the best value in a black or brown loafer.
You can't go wrong with the classic "penny loafer." There is a black and darker brown option a well.
My personal favorite in a dark brown are “Horse Bit” loafers. I love these Senner Loafers from Tommy Hilfiger. They travel easy and have a way of dressing up my suits and slacks. Fantastic Value! These horsebit-style loafers are versatile and comfortable. A perfect paring with any suit or slacks.
Tommy Hilfiger Men's Senner Loafer, Medium Brown
$49.50
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Monkstraps are an elegant yet fun look for a dress shoe. This distinct shoe style is laceless. The shoes are secured with one or multiple buckles or straps. This pair from Florsheim is my best monkstrap deal. I love wearing these with my suits and slacks.
This elegant shoe comes in a beautiful Cognac. I love the dynamic look of the straps and buckles. If you haven't tried a Monstrap, this is the deal to try; you can't beat this price for its quality and look.
Traveling in my Jousen Chukka Boots
Chukka boots are a stylish addition to any man’s wardrobe. Their design exudes a unique charm that merges formal and business casual looks, making them exceptionally versatile. Unlike Chelsea boots, which offer a sleek, polished appearance, Chukka boots, whether in suede or leather, present a more relaxed yet sophisticated aesthetic. Chukkas are open-laced instead of closed-laced or slip-on, as you can see in the pair I’m wearing in the photo.
These Retro Ankle Chukkas from Jousen are fun to wear and travel incredibly well. These Chukka Boots are incredibly stylish and comfortable. They look great with any pair of slacks because they are a nice mid-brown.
Fit True to Size
Jousen Leather Boots for Men Dress Classic Mens Boots Polish Retro Ankle Chukka boots mens
$119.00
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The right ankle boot can be your most versatile shoe. With their slim and polished profile, slip-on Chelsea boots can elevate a casual ensemble or add a relaxed sophistication to formal attire. Below are my treated grey leather-style Chelsea boots. Casual or Business Casual option. Looks and feels incredible, I will update with my own phot soon!
Fits True to Size
Ferro Aldo Sterling Mens Casual Chelsea Slip on Ankle Boots
$64.99
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I love these with jeans, and they dress up nicely as a smart casual option. You can’t beat the rustic, old-school boot style.
A great way to master the shoe and boot styles is to supplement your collection with something other than strictly ‘casual’ or ‘dressy’ categories. Instead, understand the adaptable nature of these styles and how they can be tailored to suit a wide range of occasions. By doing so, you’ll not only maximize your wardrobe but also cement your status as a genuinely fashionable professional.
Your trousers or jeans selection can significantly influence your overall look. Consider coupling dark denim jeans with Chelsea boots or black sneakers for a modern aesthetic. This combination can create a versatile yet edgy look that transitions effortlessly from day to night. Try the white sneakers or Olakais with blue jeans or corduroy for a relaxed style (Link and Photo Below, I just purchased these but have owned Olukai styles for years).
“Skinny Fit” slacks – Can go “sockless”
When navigating more formal attire, remember that the cut of your trousers is critical. Opt for tapered fit trousers to create a streamlined silhouette that works seamlessly with dress shoes or black Oxfords. This sharp look can convey a sense of professionalism and put a stylish spin on traditional business attire.
Slimmer, “Modern Fit” Slacks – Click to Shop
But don’t just stop at formal and casual wear. You can also experiment with other combinations. Try pairing high-top sneakers with skinny jeans for a contemporary, urban look, or mix-and-match loafers with straight-leg jeans for a relaxed, preppy vibe. The options are endless, and all depend on your style and the impression you want to make.
Remember, the right combination of shoes and trousers can enhance your style and help you make a lasting impression, whether at work or enjoying your free time. So, don’t be afraid to experiment and express your unique style.
Understanding how seasons impact footwear choices is integral to being a style-savvy professional. Each season brings a change in climate and a corresponding shift in fashion trends. The summer season often calls for breathable and relaxed footwear. Therefore, boat shoes and canvas sneakers are an excellent choice. They offer comfort and a laid-back style, making them ideal for casual outings, beach vacations, or simply lounging around the city. Below are my two favorites. Olukai became my “go-to” brand a few years ago. These are the most versatile outdoor summer shoes on the market.11/20/2024 11:11 pm GMT
4.5
4.4
4.5
4.6$99.95
$127.99
$63.13
$100.00
As the leaves start to fall and the temperature dips, your footwear choices should adapt accordingly. Chukka boots are perfect for autumn with their rugged yet stylish aesthetic. The sturdy construction and versatile design pair seamlessly with jeans and flannel shirts, creating a stylish ensemble that captures the season’s essence.
Rugged Leather Chukka Boot
Winter requires practical and stylish footwear. Leather boots with a robust rubber sole are the answer during these colder months. These boots offer excellent durability and insulation against the cold, while their sleek design ensures you don’t have to compromise style. For business attire, leather boots can pose a style challenge. Some Chukka Boot styles can function well in harsh winter climates while delivering on style.
Embracing the change in seasons and adjusting your footwear choices accordingly can be a fun and exciting aspect of men’s fashion if you have made affordable, versatile choices. It allows you to experiment with different styles, textures, and colors, keeping your look fresh and exciting all year round. So whether walking in the warm summer sun or trudging through the winter snow, remember that your shoes can be a statement of style and practicality, no matter the season.
I will start with a versatile Brown Chukka from Nautica if you’re looking for office-wear shoes on a budget. Here is my Amazon link for the Largo-Brown. These are vegan leather and water-resistant, and you can wear them with just about anything except black. You can grab a second pair; versatile black shoes are the way to go. Looking for suede? Jousen has this beautiful pair on Amazon: https://amzn.to/49w5mKG.
Well-informed choices can help you build a versatile, stylish, affordable shoe collection. The focus should always be on quality over quantity, as this will provide the best value for your money and ensure your shoes stand the test of time. With this in mind, you’ll be well on your way to owning a shoe collection that suits every occasion and reflects your unique style and personality.
