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How to Wear Dress Shoes Casually

As you move further along in your style journey, you may find that you have some items that are more versatile than you originally thought. That includes the dress shoe; you don’t always have to wear them with a suit. If you pick dress shoes that are the right style and the right color, you’ll be good to go.

Here are 5 different looks to show you how to wear dress shoes casually.

If you mix and match pieces in your wardrobe, some a little dressy - some a little casual, you’ll get much more of your money worth out of those dress shoes.

LOOK 1: Brown brogues with a v-neck sweater

This is a classic, go-to, dress shoe casual look. What makes the shoe a brogue are the decorative perforations around the shoe. The more broguing, the more casual the shoe is which allows you to dress it down more.

This is a look you can always rely on. It features brown brogues, your trusty dark denim jeans, and a grey v neck sweater. It's one of my favorite spring or fall looks, especially when you layer the sweater over a white button down shirt.

Another tip - the most versatile color dress shoe is definitely brown.

LOOK 2: Oxblood double monk straps with a sweater style polo and dark denim

This second look is more of a warm weather look. These are my absolute favorite dress shoes. The double monk straps are easy to dress down and ultra sexy. It’s a classic shoe but more stylish than the average guy would rock.

My favorite color dress shoe has to be oxblood/burgandy as I show in this look. It’s a great alternative to a black shoe and the color pairs well with dark denim. As you can see, I‘m rocking the dark jeans and paired this look with the sweater style polo.

LOOK 3: Dark brown loafers with olive chinos and an unstructured blazer

This is probably the easiest dress shoe to wear casually. I love the combo of olive and brown; the chinos are also easy to dress up or down. You can see the choice of an unstructured blazer is more of a casual one because it doesn't have the stiffness of shoulder pads and liner like a traditional blazer has. You can put together this stylish look to be more casual and not too dressy and stuffy.

LOOK 4: Trousers with a vest and dress shirt with the oxblood double monk straps

This is one of my favorite fall weather looks. I rock these grey wool trousers all the time and I layered a Peter Manning Vest over a light blue dress shirt. You can wear the oxblood double monk straps with almost any color. You can also wear this vest in so many different ways like under an overcoat or over a dress shirt as you see here.

LOOK 5: Tan loafers with slim fit olive cargo pants

I want to show you how versatile different versions of brown dress shoes really are. These tan loafers pair really well with these cargos. A nice slim fit, tailored style of cargo pants can be dressed up, too. Every man should also have a navy blazer in their closet as you see I have on here. This is another one of my favorite looks; these colors rocked together are a win when paired together.

Whether you’re going dressy or casual, it’s important to pick a dress shoe that's of great quality and at a great price point. That’s why I suggest you check out Becket Simonon. They provided the shoes you see in each of these looks and there’s a reason I work with them over and over. They provide high quality shoes at a fantastic value. You can’t beat that. What makes them so great is they are direct to consumer, with no wasted inventory because they don't make the shoes until you order them. They save a lot of money doing this and pass along those savings to us. There's full grained leather uppers, handcrafted construction, qnd great leather lining for comfort and breathability. They have all of your footwear needs covered from sneakers to boots and dress shoes. Becket Siminon is providing us with a 20% off code so make sure you check them out and tell them you're with the Style O.G. fam! Just use code "OG" when checking out.

Let me know which one of these looks you're going to try out in the comments.


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