Today is a good old-fashioned dress shoe tutorial. I am going to teach you how to properly wear dress shoes, because, unfortunately, many men wear them incorrectly. I see men with terrific outfits, but they’re wearing the wrong shoes. These men are trying, but are making some common mistakes which I would like to review.
First, some basic information about dress shoes needs to be covered. There are only three types of dress shoes that you need to worry about: loafers, oxfords, and monk straps. Regarding loafers, these shoes don’t have laces and have an almond-shaped toe. Oxfords are a type of lace-up dress shoe that comes in various styles, including cap toe and wingtip. Double monk straps are one of my old school favorites. It’s a bit more stylized and looks incredible with jeans, chinos, and even suits.
As you’ll see, stick with classic styles, invest in quality shoes, and match the shoe level to the level of your outfit to look awesome!
Now for the rules.
- Go for classic styles. You want to opt for classic rather than over-the-top and busy.
- The style of shoes depends on the denim worn. You should never try to dress up a pair of light-wash jeans with dress shoes. It’s too casual. You can never go wrong with a pair of non-distressed jeans. Take a look at my examples in the video.
- Brown is richer. It’s a personal preference, but I believe that brown is a much richer color. Brown looks amazing with gray, light gray, medium gray, dark gray, charcoal, brown, navy, blue, green, and many other colors. Black is a more formal shoe for a black suit or black tie affair. Brown is universally excellent and a richer, more stylish color. Beware of super light tan, however. This is a bit more outdated and hard to match. I also don’t love ox blood. It’s almost maroonish red and more old-school money.
- Match your shoes and belt. It’s a huge mistake if you don’t match your leathers. If you have a nice suede, you need to look for a belt in the same color, finish, and thickness. Don’t match by memory; instead, take your shoes with you to the store to match with a belt. Also, pay attention to the shine of the leather. Brown is a lot more nuanced with many different shades.
- Shoes with chinos depend on the dress level. In an office environment? You can’t go wrong with brown loafers. You could also do a wing tip, but do not go with a black wing tip unless it’s very formal. In other words, match the shoe level to the dress level of the outfit. You don’t want to pair something super casual with something more dressy, and vice versa.
- Quality matters. I’m a firm believer that you should stretch for the highest quality dress shoes that you can afford. That’s why I love Thursday Boots’ dress shoes.
- Avoid wearing overly square, round, or pointed shoes. You want shoes with a natural shape, almost almond. You don’t want excessively dramatic shoes, and you want to make sure your sole is not too big and bulky.
- Shoes with suits depend on the fabric. If you have a gauzy and more summery suit, such as a linen-cotton blend, suede loafers are a must-have. But don’t wear socks. If you’re in a more professional environment, where your suit is shinier or a bit more professional, avoid suede. You need shoes that are a bit shinier and polished.
- Just say ‘no’ to patent leather. These are like military shoes or when you rent a tuxedo. These shoes look plasticky. Don’t ever wear them. There’s never a time or place that these look good. Opt for something shiny without being disgusting. Patent leather is gross.
- Dress up shorts. If you want to wear a nice linen shirt tucked in or a polo shirt, opt for a loafer. Brown works with pretty much everything.
