As the last few days of 'summer' come to an end, we are left seeking warmer attire to replace slip ons, Birkenstocks and the occasional pair of flip flops.

Britain's default weather of rain, damp and cold is about to befall the nation. Now is the time for footwear of a more hardy disposition.

But it would be thoughtless, and stupid, to go straight for your dad's trusty hiking boots off the garage shelf. Yes, it may be amazing you share the same shoe size as your old man but trodding the high street looking like a lost groundsman is not a strong look. 

Boots say to the general public that you've prepared for the new season and you plan to look good. 

Here's how to wear boots...well.

Let's break it down into three easy sections... 



Morgan black

We kick off with the cardinal rule. Never wear boots with baggy pants. The point is to show off the silhouette of the boot you've splashed out on...not make yourself look several inches shorter or about to appear as an extra in Save The Last Dance.

Whether you're wearing jeans, pants or chinos, try to make them tapered or slim but never skin tight. Cost and time may be an issue but getting your pants tailored to suit you perfectly is a safe bet. With a higher heel than normal shoes, finding pants off the peg that fit well can be hit and miss.

And anyone that tucks the pants into the boot gets an automatic dismissal from the GS club. 



Tremont tan

To cuff or not to cuff. Here at GSHQ we don't judge. You want to cuff on your Chelsea boots, go right ahead.

Just remember any cuffing - deep or double - will instantly take height off your profile. You can cuff over the boots, or cuff slightly over the front with the boot pull tabs sticking out. 

Just make sure there isn't a visible gap ('the breaking point') between the top of the boot and the end of the cuff. There's nothing worse that showing a bit of bare skin or sock looking like a rejected member of Mumford & Sons.  



Sherwood, herringbone tan 

The fit should be snug but not tight. The eyelets on either side should be no less than an inch apart once your laces are tied. If the laces are too close there's too much room over the bridge of the foot and the size is too big. Conversely, if the eyelets are far apart your foot is stretching the vamp and the shoe is too small.

Next, check if the heel fits well by walking up a flight of stairs. If you can feel space between the ball of your foot and the shoe, they're likely too big.

Finally there should be about a 1/2 inch between the end of your longest toe and the end of the front of the shoe. Generally, this is about the size of the tip of your index finger (for small hands) or little finger (for large hands). 

October 17, 2019 — Simon Smith