What Clothes To Wear With Dress Shoes?

Have you ever worn Oxfords with a pair of torn or distressed jeans? Of course not, and you’ve probably never seen anyone rocking such a combination. How about monk strap shoes with a coat and jeans? Well, that’s an acceptable combination of clothes and dress shoes. That’s the cool thing about dress shoes. With the right kind of clothes, dress shoes add zip to your presence and up your style quotient. They also give you options in mixing and matching garments to shoes for an occasion. But you don’t want to end up making a style faux pas. And that’s why we’ve come up with this detailed guide on what clothes to wear with dress shoes.

What Clothes to Wear with Monk Strap Shoes?

For men who find the casual elegance of monk strap shoes appealing, these shoes are a stylish alternative to laced dress shoes. Monk strap shoes were once worn by…monks! These shoes have a European provenance and with their buckles and straps, they attract attention without being too loud. Having a pair or two in your wardrobe broadens your choice for formal and informal occasions. Loafers and Oxfords can be styled for the monk strap look. Choose from single, double, and even triple monk strap shoes to go with your suits. They blend as effortlessly with wool trousers as they do with chinos. A tuxedo with these shoes is a thought if you’re considering a tasteful pairing for the wedding you’ve been invited to. Burgundy monk strap shoes on beige trousers and a light blue button-down shirt are a winning formal combination for college.

What Clothes to Wear with Oxford Shoes?

In the context of men’s fashion, Oxford shoes are the byword for dress shoes. These shoes are the distilled quintessence of style and tradition. An essential component of every man’s wardrobe, Oxfords can be styled in different ways, both formal and informal. Black Oxfords are a very versatile pair of dress shoes that you can fall back on as a conservative option when you’re unsure of other shoes and clothes combinations. As a rule of thumb, as compared to broader Oxfords, slimmer ones are preferred for a dressy look. The clothes you pair with a pair of Oxfords will depend on the aesthetic vibes you wish to project, and this in turn depends on the occasion. These shoes have an inherent formal appeal, and if you’re planning to wear these for a semi-formal occasion then pair these with the right clothes, for example, a pair of regular fit dark blue jeans with a coat will deliver the right effect. For business meetings, weddings, and other formal affairs, you cannot go wrong with Oxfords so long as you get the color combination right.

What Clothes to Wear with Brogue Shoes?

A brogue shoe, also known as a wingtip, is a dress shoe for men that features decorative perforations, also known as broguing. By this reasoning, an Oxford shoe or a loafer featuring such detailing, is also a brogue. Originally used as shoes for the outdoors by the working class and the gentry of Ireland as well as Scotland, brogues today have evolved for wear across occasions, formal and informal. Brogues with jeans is a classic combination; the shoes can be worn with or without socks. Brogues facilitate the smart casual appearance; they gel nicely with Chinos. For formal wear, it’s a good idea that these dress shoes sport minimal broguing. Full brogues, longwings, semi brogues, and quarter brogues are styles to choose from.

What Clothes to Wear with Loafers?

Loafers are characterized by the absence of shoelaces; these slip-ons are comfortable and very versatile. They’ve evolved from being a highly preferred pair of footwear for casual outings to gaining acceptability as dress shoes that you can wear with lounge suits. As loafers can also be worn without socks, the gap between trousers and the shoes is a consideration. For casual occasions, you can wear loafers with Bermuda shorts, jeans, or basically anything that is acceptable for casual settings. Leather loafers, tasseled, kilted, or with bells, are perfectly acceptable dress shoes for formal occasions. Whether as footwear to accompany a semi-formal three-piece suit or a coat-and-tie formal combination, you will assuredly create an impression with loafers.

What Clothes to Wear with Derby Shoes?

In the hierarchy of dress shoes, open-laced derby shoes are regarded as slightly less formal than the closed-laced Oxford shoes. Nevertheless, these shoes can be worn with formal attire and are a good choice for occasions with formal dress codes. Plain derbys, without embellishments such as broguing, are the preferred design in derby shoes for formal settings, such as black-tie dinners. These go well with day suits, too. For occasions that straddle the zone between formal and casual, you can easily wear cap-toed derbys or wingtipped derbys with jeans and a semi-formal shirt. For a more casual and relaxed look, suede derby shoes with t-shirts and corduroy pants are a good idea.

What Clothes to Wear with Opera Pump Shoes?

Opera pump shoes, also known as court shoes, are considered as the ultimate expression of formal footwear. The slim profile of these shoes displays all the characteristics expected of formal footwear and is an excellent choice for pairing with suits, especially for white tie occasions, and can be worn for black tie events. These eveningwear shoes, sporting bows, are worn indoors, and their color should ideally match that of the necktie. If you’re dressing up for a high-society event, then wear pump shoes.

How to Pair Dress Shoes with Jeans?

As mentioned above, denim pants, also known as jeans, can be tastefully combined with dress shoes, such as loafers, chukka boots, brogues, derbies, monk straps, etc. Basically, there’s a simple rule to follow. Jeans that are more dressy than casual, and dress shoes that have a broader profile are an ideal combination. Open-laced shoes that can be worn for formal and semi-formal occasions as well can be paired with jeans. Dress shoes are invariably in shades of black and brown. You can match or contrast the color of the shoes with that of the jeans.

Dress Shoes and Color Considerations

When pairing clothes with dress shoes, it is important to factor in the color of the dress shoes. The right colored shoes will complement the outfit and deliver the desired effect whereas poor choice in color can detract from the overall look even when you’ve taken pains to get the shoes and outfit combination right.

You can safely go by the trusted maxim of lighter shades tending towards a casual look while the darker ones appeal more to formal occasions and sensibilities. Combine this information with the knowledge that wider dress shoes are more apt for semi-formal and casual occasions, and you have a basis for matching outfits with dress shoes. Brown, in its many shades, is a versatile color that you can safely pair with suits as well as jeans. All you have to do is to select the right shade and the right shoe type. So, while brown loafers or brogues are apt for casual or semi-formal settings, you’re on safe ground with brown Oxfords for a formal affair.

Once you develop a feel for the right color, you can freely mix and match colors according to the occasion and the mood. Oxblood-colored dress shoes can be a statement in extravagant style in formal settings when paired with navy-colored suits, or you can rock a casual look with Oxblood loafers with faded jeans.

Women’s Dress Shoes and Outfits Pairings

Let’s take a look at the outfits that can be paired with women’s dress shoes.

What Clothes to Wear with Heels?

While jeans knickers with heels and sweatpants with stilettos are obvious fashion blunders, there exist enough and more dresses and outfits, including jeans that women can pair with heels. Black heels are versatile dress shoes and combine particularly well with brightly colored dresses. Bright colored heels, for example red, can be worn with matte shades of brown or with black dresses. Kitten heels are a great idea when you’re in the mood for a casual yet chic appearance, wear these with knee length skirts and show off those toned calves. Match stiletto heels with eveningwear gowns or ankle-revealing pants.

Cool Oxford and Brogues Pairings for Women’s Clothes

Oxfords have a reputation for being dress shoes, but with a little creativity women can style Oxfords in different ways to span the range from casual to formal, covering all the looks in between. Oxford shoes and women’s jeans are a fail-safe combination when you’re in the mood to exude some restrained flair. Dress pants, flowery prints and all, make for yet another time-tested combination with flat Oxfords; a great idea for spreading some classy and casual vibes. Brogues let you straddle the realms from formal to smart-casual and beyond…to informal wear. These are versatile dress shoes. Pair them with trousers, shirt, and a coat to dress up. You can dress down by wearing these with printed blouses and casual-wear pants.

Sarah Shawman

is the webmistress of Footwear 4 Workers.

She started this website out of displeasure with the fact that there are so few good online resources especially dedicated to the 99%: working people. Having suffered from work related plantar fasciitis herself, she set out on a mission to help others.

She updated this page on and will continue to update it as time goes on.

Submit a Comment

Your email address will not be published. Required fields are marked *