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Matching the Shoe to the Occasion

Before we start to look at the specifics, it’s important to acquaint yourself with the types of shoe that can be worn with a suit. Not every style of footwear listed here is suitable for all dress codes, but each can be worn with tailoring in one way or another.

The Derby 

The Derby shoe is the businessman’s best friend. A timeless workhorse that can transition from boardroom to bar seamlessly. Recognisable by its open lacing system, the Derby is less dressy than its Oxford counterpart but still more than smart enough for anything except black tie. 

The Oxford

Think of the Oxford as the Derby’s smarter sibling. In patent leather, it’s the go-to shoe for black or white tie. Subtle detailing dictates how formal or informal an Oxford shoe is. Additions such as toe caps and perforated decoration known as “broguing” can give certain styles a more casual edge. Which brings us to our next shoe type.

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The Brogue 

It is, in fact, possible to have an Oxford brogue or a Derby brogue – the common thread is that both feature some level of broguing to the upper. Often this detailing will be accompanied by additional panels of leather, such as heel cups and wingtips, which lend the shoe a more decorative feel. At its core, this is a smart casual shoe.

Tan Brogue Shoe | Simon Carter

The Monk Strap

A slightly more adventurous option, suitable for everything from cocktail attire to business use, look no further than the monk strap. This modern menswear favourite is essentially an Oxford shoe with either a single or a double strap fastening to lock the foot into place.

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The Loafer  

Another laceless style, the loafer is the perfect option for less formal occasions or business casual offices and is an obvious go-to where cropped suit trousers are involved. The perfect option to go with chinos, shirt and a casual jacket Choose between suede and leather depending on the vibe you’re going for; leather is smarter, suede more relaxed.

Tan Suede Tassel Loafers | Ladies Country Clothing | Cordings

The Smart trainer  

In years gone by, pairing tailoring with a trainer of any sort was the gravest style sin a man could commit. Today, however, it’s perfectly acceptable provided the dress code permits and that it’s done with a bit of thought. For example, a pair of crisp white leather sneakers teamed with modern cropped wool trousers gets a big thumbs up. A battered old pair of Converse and a tux, on the other hand, not so much.

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Now we know the styles of shoes and what to wear them with, lets take a look at what shoes work best at each event.

First of all we have the Cocktail party

Of all the possible dress codes, cocktail attire offers you the most freedom when it comes to deciding on a pair of shoes. Brogues are perfectly acceptable, as are monk straps. But for the best look I believe suede/leather loafers, or even a pair of smart trainers. For best results, couple either one of these with a cropped-leg trouser and no-show socks. And remember, where your tailoring is concerned, blazer and trouser separates are fair game here.

Now onto Black-tie

Black tie is about as strict as dress codes come, but that’s not necessarily a bad thing. All it means is that there’s less chance to get things wrong, which is good news if you’re one of the many men who struggle when it comes to formalwear. Black patent-leather Oxford shoes are the classic choice here. That said, a regular leather pair of Oxfords will suffice – just make sure they’re clean, polished to a shine and scuff free.

Last of all we have Business

As far as your weekday attire goes, the best shoe for the occasion is a classic Derby. This timeless staple is the perfect marriage of dressy and casual and can even work as part of your off-duty wardrobe provided you buy well. Remember, when it comes to purchasing footwear, you get what you pay for and in this case you will be wearing the shoe a lot.