When it comes to your outfit, how you use men's dress shoes can either make or break the look. Depending on the style and color, they can blend flawlessly with the whole shebang, or even be the centerpiece.
So, how does one go about building an outfit around their shoes? It's easier than it sounds! And it's the topic of today's article. We're going over some steps to make an outfit from the feet up! To do this, I've decided to combine four different pairs of shoes with a few streamlined outfits:
- A classic navy suit – formal, elegant, and sleek.
- A casual gray suit – still a complete suit, but with some more texture – less suited (see what I did there?) for formal events.
- Dark green sports jacket with gray flannel trousers – a business-casual outfit.
- Navy jeans, blue sports shirt, olive field jacket – a well-fitted but totally casual outfit.
Got it? great, let's get into it.
1. Wholecuts
These shoes are a modern classic – about as sleek as you can get in a dress shoe. What sets them apart is the fact they're made with a SINGLE piece of leather. It also makes them pricier, as the leather needs to be absolutely top-notch to cover such a wide area. Still, they're well worth it! They're as formal as men's dress shoes go. In fact, you could wear them in the same capacity as a classic cap toe Oxford.
So, how do they fare with clothing?
- Classic navy suit: Medium brown Wholecuts work well with a navy suit. They stand out just enough without drawing too much attention and there's very little contrast. Seeing as how Wholecuts count as a formal shoe, you can easily get away with wearing them alongside formal attire.
- Casual gray suit: Though the medium browns work with a more casual gray suit, it's oxblood that steals the show here. It adds a bit of flash that you can rock without fear.
- Dark green sports Jacket with gray flannel trousers: The oxblood Wholecuts were a little bold here, especially against the more subdued colors on this ensemble.
- Navy jeans, blue sports shirt, olive field jacket: The Wholecuts are too formal for this outfit in my opinion. Don't get me wrong, you could pull it off if you have the confidence, but it's not something I recommend turning to on a regular basis. The elegance of the Wholecut clashes too much with the ruggedness of the outfit.
Wholecuts are amazing – both in style and in their construction. However, the smooth figure and high cost mean that they don't work as well as workhorse shoes. Rather, you should save them at least for situations requiring a casual suit.
The oxblood (pictured above) works extraordinarily well in instances where black men's dress shoes would do the job. The big difference is that oxblood delivers a color punch that makes you stand out without going overboard.
2. Double Monks
Monk Straps have been around since the middle ages when friars developed a shoe with a buckle that made intense labor just a little more bearable. They've become more popular in the last 20 years, and in the last 10, they've exploded on to the scene. The two best things about them? The flash and versatility. The buckles offer a bit of an eye-catcher without overcompensating.
Let's try them out:
- Classic navy suit: Double Monks do work with the navy suit, but I'd hesitate to make this a habit. I think of them as more of an eye-catching casual men's dress shoe. Pairing them too often with formalwear can draw unwanted attention. People might gain the impression that while you do care about style, you may not have enough money to buy more than one pair of shoes.
- Casual gray suit: The shoes feel right at home here. They're elegant enough that they mesh well but casual enough that a textured gray suit fits them like a glove. Overall, this is a great combination you can easily take to the office.
- Dark green sports Jacket with gray flannel trousers: Similarly to the gray suit, things are looking good. You could easily sport Double Monk Straps with a business-casual setup.
- Navy jeans, blue sports shirt, olive field jacket: They threaten to overpower the outfit with how elegant they are at a glance, but they actually go well! Brown Double Monks with navy jeans and green jackets are a compelling combination.
What's the verdict? Double Monk Straps are coming into their own as a fashion trend. While I usually knock on trends as fleeting, I'm making an exception for these. These men's dress shoes steal the show with almost every outfit, just make sure to err on the side of casual here.
3. Chelsea Boots
What about taking it up a notch with some dress boots? Chelsea boots have a heck of a heritage. Though the Beatles brought them into prominence in the 60s and 70s, they actually date back to the Victorian era. The Chelsea Boot Company developed them in England as cavalry boots. The key feature in these men's dress shoes are the elastic bands along the sides (They were originally vulcanized rubber). Thanks to them, the boot slips on and off with ease.
Let's get down to business:
- Classic navy suit: Dark brown Chelsea boots work amazingly with this combo. They're so sleek that it meshes effortlessly with the suit. Now, I did try some brown suede variations… yeah, not great. There's just too much contrast in the outfit – the rugged nature of the suede doesn't go with the formality of the navy suit.
- Casual gray suit: Chelsea boots are great in both brown leather and suede. It's hard to go wrong here, but I'd err on the side of the leather. It could easily be argued that suede is too casual even for a suit like this.
- Dark green sports Jacket with gray flannel trousers: The leather and suede work perfectly well in tandem. It hits that perfect balance of casual and elegant that allows for both materials to shine.
- Navy jeans, blue sports shirt, olive field jacket: Both work here, but there is a difference depending on the material you choose. If you want to go ultra-casual, then suede stays true to your style while looking laid back. Dark brown leather, however, elevates it JUST a bit, making the overall look perfect for a night out in the town.
All-in-all? This is a extremely useful boot to have. It's the single most versatile piece of footwear on this list. Even though suede didn't go too well with the navy suit, it rocked on the other three. Every man should have a pair of Chelsea boots in their closet.
4. Sneakers
I admit I'm having a bit of trouble getting into sneakers, but it's a pretty simple category to go through. Ready? Here we go:
- Classic navy suit: NOPE – way too casual. Color doesn't even make a difference here.
- Casual gray suit: This might work if you're a rockstar… but otherwise, I don't recommend it. Avoid this combo.
- Dark green sports Jacket with gray flannel trousers: We're starting to see progress here. I can see guys rocking this if they have the gumption, but it's still iffy at the end of the day, business-casual does not go with sneakers.
- Navy jeans, blue sports shirt, olive field jacket: The only outfit that I felt absolutely comfortable in wearing sneakers. The equation is simple: Casual goes with casual!
The verdict is that sneakers are not versatile. They aren't even as useful as the Wholecuts! Yet, men overuse them for more than is appropriate these days. Nevertheless, you're not most men! Keep in mind that sneakers should only be used in the most casual of circumstances.
Summary – Men's Dress Shoes
When it comes to building a wardrobe from the ground up, we covered some good ground with some essential shoes. We know that some dress shoes are more adaptable than others, but with knowledge, you can knock it out of the park!
