Your Guide to Business Casual Shoes

You may not be able to judge a book by its cover, but you can certainly judge a man by his shoes.

Men’s business attire is becoming increasingly more casual; casual Fridays have stretched into Thursdays and the strict black suit, white shirt combination is almost a thing of the past. As the rules of men’s business wear break down, some guys have got lost in a style limbo, with outfits somewhere between a lounge suit and loungewear.

Don’t let your fashion choices ruin your professional ones. Follow this simple guide to men’s business casual shoes and you’ll be right on the money.

Mens Business Casual Footwear

Loafers and Moccasins

Loafers and moccasins are the most obvious choices for business casual shoes for men as their slip-on style and simple design gives them a real ease; it’s hardly surprising the style originated as a house slipper.

These two styles are very similar, the main difference being that loafers have leather soles and heels whereas moccasins don’t. Instead of leather soles, moccasins have rubber pebble soles. While this may seem purely aesthetic, its important to bear in mind when choosing your business casual shoes because, if you’re heavy footed, you will wear through the rubber pretty quickly. Additionally, if you are short, a loafer with a heel will give you added height.

For two simple shoe designs moccasins and loafers are really versatile and will suit a wide range of men. If you like understated, easy-going shoes, a pair with a penny strap or simple laces like driving shoes are great options for business casual. Be careful not to stray into boat shoes, as they are too casual for work.

Slightly smarter still are loafers or moccasins with a horsebit strap. If you fancy yourself a bit of a sartorial gentleman, go for a structured suede loafer with a tassel. These often have chisel toes that make the shoes appear slimmer, and so sharper and more elegant.

Their classic and understated silhouette are so versatile. G.H. Bass & Co. swear by them for international business travel. They feel like the most comfortable pair of slippers you could own that look smart enough for high profile meetings with Industry VIPs.

– Design team at G.H. Bass & Co.

Oxfords and Derbys

If you’ve just started a new job and aren’t quite sure of how casual business casual is in your office, go for an Oxford or Derby shoe. These have long been the classic office footwear choice for men, so why mess with a good thing.

For lots of guys, Oxford vs. Derbys is a minefield. A foolproof test to differentiate between the two is to run your finger down the laces and see if you can follow the gap between the leather round the bottom curve. If you can, the laces are open, meaning the shoe is a Derby. If you can’t because the fabric is stitched down, it’s an Oxford.

Derbys are typically more casual as the open laces allow for a wider shoe that’s much easier to slip on. To get a more casual vibe from either style avoid heavy black leather that has become the trademark shoe of formal office attire. Instead, choose shoes in brown leather or coloured suede.

Monk Straps

The Monk Strap is a modern alternative to the traditional Oxford or Derby and is a perfect example of a business casual shoe: though ironically they are centuries old, designed by monks who wanted more substantial footwear than sandals.

You can choose between one or two straps. They are a great option for straddling the casual/formal boundary. On the one hand, the classic shape and option of broguing (the dotted pattern made by holes in the leather) and wingtips (the w shape on the toe of a shoe) make them semi-formal, while the strap and buckles add a modern element that keeps them cool.

Like Oxfords and Derbys, Monk Straps traditionally come in leather, but you can also find them in coloured suede. Dark chocolate leather Monk Straps have a warm, luxe style that will look good in winter and summer. They are a great way of showing you have style without screaming it.

Dress Boots

On to boots: there are several styles of dress boots that make perfect options for men’s business casual footwear. Boots can be worn all year round so don’t rule them out simply because you see them as winter-only shoes; though given British weather this is a big advantage boots have over suede moccasins for example.

Dress boots are essentially Oxfords, Derbys or Monk Straps but in boot form. Like their shorter counterparts, dress boots can either have open or closed laces or straps as well as additional features such as broguing and wingtips.

They also come in a variety of lengths. Choosing a length is quite subjective and can depend on the width of your ankles and lower calves.

For business casual attire, you need to find a balance in between overly bulky Doc Martins and slouchy biker boots; neither is appropriate for work. Instead, a pair made from relatively robust leather that looks tidy and can be easily polished will make fantastic business casual shoes.

Chelsea Boots

While loafers and brogues may go in and out of style, Chelsea boots are a timeless option for men’s business casual shoes. They exude effortless style and sophistication, making them an excellent choice for men’s business casual footwear.

Chelsea boots are a bit like horse riding boots in that they’re ankle length, have a low heal, rounded toe (traditionally at least) and, most iconically, feature elasticated side panels that make them easy to put on and take off.

They are traditionally made in leather but now come in suede and other relaxed materials ideal for business casual shoes. Unlike dress boots, Oxfords or Derbys, the simple, plain design of Chelsea boots mean they still look casual in black leather.

Chukka and Desert Boots

Chukka boots are the most casual option for men’s business casual footwear. They are ankle length boots with rounded toes, minimal stitching and open lacing similar to the Derby. They are traditionally made of soft suede, but you can also get polished leather versions if you want a more formal look.

They shouldn’t be confused with Desert boots which are more casual still, often featuring much less structured suede and a rubber sole, although they can also be a good choice for men’s business casual shoes.

The desert boot really is one of the most versatile pieces of footwear in the world. Depending on the type of trousers worn, it completely changes how the shoes look. For a more formal and work friendly aesthetic, wear them with tailored trousers. Pair them with some relaxed and faded selvedge denim and you have an iconic casual look.

– Jacob Bizley , Originals product line manager

Business Casual Dress Code

Now that you know the different shoe options out there for business casual attire for men, here are some tips on what to wear them with.

First thing to remember is that perfecting the business casual look is all about balance. While there’s nothing wrong with wearing statement clothing you don’t want to look chaotic with too many colours or patterns. For instance, if you choose a brightly coloured shoe tone down the rest of your outfit. Starting from the casual shoes for men and up, this is how to build the perfect look for work.

Mens Business Casual Shoes and Jackets

There are three top choices for business casual jackets: a navy or grey blazer, a short, tweed jacket, or, this one may surprise you, a nice corduroy jacket. A light, neutral colour acts as a welcome contrast from the usual dark office wardrobe.

Getting a jacket that fits you is essential with business casual attire. If you can’t find a blazer than fits your body shape you can easily get one nicely tailored without having to pay Savile Row prices. If you don’t want to wear a jacket, you could always go for a waistcoat. Alternatively, move further away from classic business wear and simply layer up with a thick wool cardigan or v-neck jumper.

Trousers

A top tip for nailing men’s business casual attire is to choose trousers in a different colour to your blazer. This doesn’t have to be a radical contrast; you could pair a navy jacket with dark wash jeans. Wool blend trousers and khakis are good options for men’s business casual.

Whatever trousers you go for, make sure you have a pair that fits; a slim leg is ideal, as it looks neat and sharp. Do not even think of wearing a pair with a rip or loose threads.

Cropped or upturned trousers that cut at the ankle go really well with slip-on shoes like moccasins and loafers. If you go with this look don’t wear socks: eliminating at least one of the many choices you have to make when choosing your business casual outfit. In the winter, cropped trousers will look great with boots that go above the ankle.

Depending on your workplace, jeans may not be considered office appropriate, but if they are, denim is a great choice for men’s business casual attire as it is understated and will go with almost any shirt, jacket and shoe. Just because you can wear denim, doesn’t mean you can wear an old pair of dirty jeans. Stick to solid, dark washes.

Shirts

Shirts are still a must for business causal attire for men; you are still in an office after all. But you have a lot more freedom with colour and pattern than you would do the rest of the week. Stripes and plaid shirts are great choices for business casual wear. Even denim shirts are an option, as long as you’re not wearing jeans.

If you really don’t want to wear a shirt, a wool or cashmere crewneck is a great choice for men’s business casual attire. As a general rule, it’s often best to go for a darker shirt if you have light trousers to balance out the upper and lower parts of your body.

Accessories

Keep your accessories minimal and understated. Pocket squares can bring colour to a monotone jacket, or a nice watch will add a business appropriate finishing touch to an outfit. Ties aren’t needed in business casual attire, but if you really want to wear one go for a more casual knitted tie. Instead of a leather belt, try a coloured woven belt. If you do choose a leather belt, make sure you match the colour of the leather to your shoes as it shows you have thought your outfit through.

“I love the combination of a denim shirt with slacks and a desert boot. It works because the dark colors are completely office-appropriate. Even though this look can be conventional, the details make it interesting—flipping up the jacket sleeves, cuffing the jeans, wearing a vintage belt. Dishevelment mis perfectly with polish.

– Frank Muytjens, J. Crew