A topic that is always good for discussion, which usually ends up in subjective opposing views, is more likely than not, a topic that is worth revisiting. And while I am pretty sure that I have never brought up this topic before, I believe that there are many opinions about the subject at hand. Since I am currently dressed in the fashion that I am presenting, please allow me to share with all of you, my subjective viewpoint on loafers with suits.
While an oxford will always be a more formal shoe than a loafer there are still many options of slip on's that are elegantly compatible to a suit. Anybody who says otherwise needs to learn that the so called 'rules' set out by well-dressed gentleman many years ago, were not the 'end all be all' and definitely do not dictate what one should wear but rather guide them to dressing elegantly. After that, style sets in and people decide for themselves (based on personal preferences) what will look good on them. Some of them pull it off and some of them don't.
Now the beauty about wearing loafers with your suits is that you are able to show off your socks. But this is dangerous game, because there is a fine line between doing what looks good and doing something that is horribly off. I have my own opinions about this and I will present them here as we shall go through what works and what doesn't.
Shoes By: Hugo Boss
Wearing socks that match your suit are generally regarded as a safe way to go. Granted, it's not always that fun as it kind of just blends your suit into your shoes, but it's always a sure way to not drag attention and to look more on the elegant side of things. However, you can spice it up while still playing it relatively safe by having a two-toned sock with one color matching your trousers and the other of a complimentary color. That way you are being safe but also adding a bit of spice to your outfit. Me being the style freak that I am, I usually will like to have that complimentary color (the one that does not match my trouser) match either my shirt or my tie.
Shoes By: Poulsen & Skone for Gieves & Hawkes
Before coming to England, I used to love wearing striped socks (like the ones I am wearing above) and quite frankly still do, but must admit I have been overtaken for an admiration of bright, solid color socks that you find many British men wearing. As you can see here, my friend and colleague, Stuart, is doing the right thing in this scenario by pairing complimentary colors coming from his shoes, socks and trousers (navy suit). So, when I say that this look is 'sometimes', it's because there are instances when people become a little overzealous and start wearing socks that completely clash and stick out like a sore thumb, causing a bit of overkill. Sorry that I don't have an example of that, but I am sure that you will know what I mean at the first instance that you see it.
Right Picture Courtesy Of: The Sartorialist
While Lapo Elkann is a dandy and wears some of the coolest outfits, and the guy on the right is incredibly sharp, I just find it very hard to appreciate the idea of going sock-less when wearing a sharp suit or black loafers. To me, it's just big clash, from the look to the elegance of it to the fact that neither one of these people are in a tropical area. Granted, there is a place and a time and a color of suit and loafers when wanting to go sock-less, but neither one of these cases fits the criteria. Wearing a linen suit, with some brown (or lighter shades of color) loafers, in an area that is humid, sunny and full of palm trees, smoking a cigar with your Borsalino hat on: this is time for going sock-less with your suit. But having a navy suit with black loafers, just doesn't mesh. It's too trendy and not timeless and therefore I give it the thumbs down.
And while there is no right or wrong, there definitely is what looks good and what doesn't. Now, coming from a relatively non-traditionalist background, my rules are pretty lenient. Others however, would not even pair loafers with suits, but that way of thinking is not going to be around much longer. So, if you have always been on the fence, give it a go, and play around with your socks, because I can tell you, the people who make me look twice at their outfits are the ones who are going bold but also staying classic and elegant at the same time. Figure that on out!