The Trouser, Socks & Shoes Conundrum

Sometimes it’s the simplest of things that can cause you the most frustration. Whether it’s that one tie that just can’t be knotted at the right length or that button on your cuff that just won’t button, we all have occasions when a molehill becomes a mountain.

I found myself in this exact situation a few weeks back when considering shoes, socks and trousers – and what colour goes with which. I was standing in my room wearing my new olive chinos, teamed with a blue Oxford shirt and navy shawl-neck cardigan, and completely drew a blank on what shoes to wear. I hadn’t even got on to choosing a pair of socks yet!

The problem I was having was that I needed to dress a little more conservative, due to where I was heading, so my go-to combination of bold patterned socks and beat up white bucks just wouldn’t cut it. Oddly enough, the creative and colourful side of style comes easier to me than the more subtle, conservative elements.

As per usual, this got me thinking about whether other people have this sort of problem. Because if I’m struggling then there must be others out there that are in the same boat, if not out of the boat and sinking to the bottom of the big blue.

With this in mind, I have decided to put together a simple guide on how to combine your trousers, socks and shoes for those occasions where you need to appear a bit more refined – be it during business hours, at a formal event or meeting the parents. Hopefully it will help put my, and your, troubles to bed.

The Sock Situation

Firstly, let’s clear up this part of the problem. The general rule you should stick to here is to make sure your socks are the same shade or darker than your trousers. For example, blue trousers = navy socks and mid grey trousers = charcoal socks.

However, as with any truly scientific law, there is an exception – and it comes in the form of brown. Within the spectrum of brown I’m including beige, tans and khakis, just to be clear. In this situation, ensure your socks are a shade darker than your shoes. I generally find that this approach also works when you are wearing olive or burgundy trousers.

What about a suit trouser with stripes or checks? Simple: pull out the colour of the less dominant stripe. For example, a navy trouser with a grey check calls for some grey socks to highlight the pattern.

What about a stripe or patterned sock? Firstly, make sure it’s not too in your face. Secondly, use the dominant colour of the pattern as your base. So a navy sock with thin white stripes is going to be paired with your blue trousers.

Example Combinations
  • Topman Navy Herringbone Skinny Fit TrousersTopman Navy Herringbone Skinny Fit Trousers
  • Pantherella Ribbed Sea Island Cotton-blend SocksPantherella Ribbed Sea Island Cotton-blend Socks
  • Reiss Poker T Classic Work Trousers GreyReiss Poker T Classic Work Trousers Grey
  • 5 Pairs Of Reinforced Heel & Toe Socks5 Pairs Of Reinforced Heel & Toe Socks
  • Reiss Alsace T Cotton Linen Mix Trousers StoneReiss Alsace T Cotton Linen Mix Trousers Stone
  • 4 Pairs Of Freshfeet™ Ultimate Comfort Socks With Silver Technology4 Pairs Of Freshfeet™ Ultimate Comfort Socks With Silver Technology
  • Asos Brogues With Leather SoleAsos Brogues With Leather Sole
  • Topman Premium Grey Check Heritage Fit Suit TrousersTopman Premium Grey Check Heritage Fit Suit Trousers
  • 3 Pairs Of Non Elastic Wool Rich Socks With Silver Technology3 Pairs Of Non Elastic Wool Rich Socks With Silver Technology
  • Topman Navy Flannel Skinny TrousersTopman Navy Flannel Skinny Trousers
  • Gant Breton Stripe SocksGant Breton Stripe Socks
The Trouser/Shoe Equation

Now for the real brass tacks. Because unless you enjoy no break in your trousers or cuff them a lot, the only time people will see your socks is when you sit down – whereas your trousers and shoes are on display all the time. So obviously, there’s slightly more to consider here.

I think the simplest way to break it down is by knowing what shoes go with the trousers you’re planning to wear, rather than the other way around. One of my favourite sources of inspiration is GiltMANual, and they recently posted an excellent diagram that explains just that:

GILTmanual - Shoes and Trouser CombinationsGILTmanual’s Excellent Visual Guide To Trouser and Socks Combinations

Essentially:

  • Blue trousers = brown/black shoes.
  • Grey trousers = brown/black shoes.
  • Brown trousers = brown shoes.
  • Black trousers = black shoes.
  • End of.

    Well, not quite. There are always going to be a few curveballs. For example, what about the aforementioned olive trousers? Well, personally, I usually stick to brown, especially a darker shade, but I think black can work too, along with another lesser used colour: oxblood.

    Better known as burgundy, it’s ridiculously popular with our cousins across the pond in America and I find it to be the shoe that can go with just about any colour of trouser and sock. But perhaps that’s just me.

    However, I strongly advise that you invest in a pair if you ever get the chance – a penny loafer would be ideal for this coming spring/summer.

    Example Combinations
    • River Island Perry TrouserRiver Island Perry Trouser
    • Allsaints Suke TrouserAllsaints Suke Trouser
    • River Island John TrousersRiver Island John Trousers
    • Heritage Grey Relaxed Fit TrousersHeritage Grey Relaxed Fit Trousers
    • Allsaints Merit ShoeAllsaints Merit Shoe
    • Asos Tassel Loafers In LeatherAsos Tassel Loafers In Leather
    • Topman Fiz Black Pointed Smart ShoesTopman Fiz Black Pointed Smart Shoes
    • Allsaints Conduct ShoeAllsaints Conduct Shoe
    • Topman Brown Herringbone Heritage Fit Suit TrousersTopman Brown Herringbone Heritage Fit Suit Trousers
    • Allsaints Preston TrouserAllsaints Preston Trouser
    • Topman Khaki Slim Smart TrousersTopman Khaki Slim Smart Trousers
    • Asos Slim Fit Suit Trouser In KhakiAsos Slim Fit Suit Trouser In Khaki
    • Reiss Stasko Tassel Loafers TobaccoReiss Stasko Tassel Loafers Tobacco
    • Grenson Dylan Black BroguesGrenson Dylan Black Brogues
    • H By Hudson Gould Tan Leather Derby ShoesH By Hudson Gould Tan Leather Derby Shoes
    • American Apparel Logan Shoe By BassAmerican Apparel Logan Shoe By Bass
    Final Word

    So there you have it, a brief breakdown of all there is to know about pairing your trousers with your socks or shoes, and all that’s in between.

    But why not tell me what you think? Did I get it all terribly wrong? How do you normally solve this problem?

    Let me know in the comments section.

    Matt Allinson