Pulling it Off: How to Wear a T-shirt with Dress Shoes and Jeans

Going out for a casual evening? A movie date? What shoes should you wear with those nice pair of jeans?

Wearing a T-shirt with dress shoes can go wrong in so many ways. Many men avoid it. However, with a little bit of guidance, you can learn to pair dress shoes, T-shirt, and jeans like a professional stylist.

Men who can pull off dress shoes and T-shirt definitely stand out. They key is to remember a few essential rules, which includes to always have a proper shoe stretcher handy!

If you want to look like a picture out of a men’s fashion newspaper, these are the rules you should follow to pull off T-shirt with dress shoes and jeans.

Select the Right Jeans

There are many types of jeans to choose from, making it easy to select the wrong one. All jeans tend to be very casual. However, some jeans are definitely dressier.

Jeans to avoid with dress shoes include jeans with holes in them and distressed jeans. It’s also advisable to stay away from jeans with a light wash.

Select jeans that fit you well in the hips and waist. Also, make sure the jeans are not too long, forcing you to make aggressive folds for them to fit. Instead, find jeans with a tapered fit at the ankles – these tend to go best with T-shirt and dress shoes.

Another important tip to remember is to avoid baggy jeans. Regular cut or slim cut jeans go best with dress shoes.

Unlike the size or fit of the jeans, there are no strict rules around the color of the jeans. Generally, dark colored jeans tend to go well with most dress shoes.

If you’re looking to be a bit more adventurous, you can contrast the color of the jeans with the dress shoes. As long as the size and fit of the jeans are just right, you’ll successfully pull it off.

A crucial men’s styling tip is to reduce the difference in formality between the jeans and the shoes. If the jeans are outlandish and the shoes are formal, then you will look out of place. To avoid this, stick to jeans that fit you well as these come off as casual, but still formal enough to look good with dress shoes.

Pairing the Right T-shirt with Dress Shoes

Pulling off the right look doesn’t just depend on your shoes and jeans. The choice of T-shirt also plays an important role.

When styling a T-shirt, avoid ones that have too many graphics. Like with jeans, the key is to lower the difference in formality.

This means outlandish T-shirts with very bold graphics will ruin your classic look. Instead, opt for shirts with plain colors or simple solid stripes. Plain colored t-shirts avoid drawing too much attention to your chest.

Another important tip to remember is to coordinate your outfit. Despite how well appointed the outfit seems. For example, a green t-shirt and red dress shoes contrast (and not in a good way!).

If your shoes are black, go for a black T-shirt. The colors don’t necessarily need to match but they should be in harmony with each other. For instance, brown shoes go well with olive colored shirts. Compare the color of your shoes and your jeans to make sure you have the right mix of colors.

Select the Right Shoes

The shoes are key to pulling off the T-shirt with dress shoes look. The shoes you select need to fit your look. This takes some forethought and careful selection.

Brown is the most popular color choice for shoes paired with jeans. Capped shoes or brogues make a great choice. If you already have a pair, but suffer from some light sole damage, then you can definitely get them back in tip top shape by using premium shoe glues.

The key to selecting the right shoes is to choose ones that are roughly the same level of formality as the jeans. Below are some tips on styling dress shoes with jeans.

Selecting Dress Shoes to Wear with Skinny Jeans

Skinny jeans are one of the most popular styles of jeans for men. You probably have a favorite pair that you’d like to wear with dress shoes. Skinny jeans are sleek and perfect for pulling off a T-shirt and dress shoes look.

Several dress shoes go well with skinny jeans – it really boils down to your taste. One of the best types of dress shoes to pair with skinny jeans is loafers. Loafers come in many different styles. For a casual look, select beige or black loafers to wear with dark-colored skinny jeans.

Selecting Dress Shoes for Slim Fit Jeans

Slim fit jeans are a good alternative to skinny jeans but are less tight fitting and more comfortable. Slim fit jeans are also good at giving off a tailored look that makes you look svelte.

For a powerful look, pair your slim fit jeans with boots such as Dr. Martens. If you choose to wear less bulky shoes such as loafers, try turning up the jeans to give off a relaxed vibe.

Selecting Dress Shoes for Black Jeans

Black is one of the most popular jean colors. Black seems to suit everyone well. Thankfully, almost all dress shoes are easy to match with a pair of black jeans.

If you follow the advice given above on the right fit of jeans, you should have no problem finding an appropriate pair of black jeans. For a simple but effective look, pair a well-appointed pair of black jeans with matte dress shoes.

Selecting Dress Shoes for Grey Jeans

Another popular color of jeans is light grey. With grey jeans, you can wear suede dress shoes in a similar color to look uniform and stand out. Darker tones of grey in jeans are more formal and give you a wider range of choices. Always remember to use some form of shoe protector spray for your dress shoes, this will prevent them from being stained too easily and will guard them from acidic rain damage.

With dark grey jeans, you can wear more formal dress shoes such as monk straps or brogues. The formal dress shoes with dark toned jeans maintain the air of formality, giving you a sleek look.

Look Good and Feel Good

The right pairing of a T-shirt with dress shoes and jeans will leave you looking good and feeling good. If you already have a great dress shoe and the only problem is they have bad odor, then there are countless shoe sprays which will help deodorize the shoes, check out our selections.

Remember that confidence is the crowning jewel once you choose the right outfit. If you want to explore more options for stylish wear, check out our page.