Toronto Fashion Week – a guide for middle-aged men

When people stop me on the street and ask for autographs or pictures, the ladies will often ask me when I’m going to write about Men’s fashion, given my impeccable, age-appropriate style and looks.  It seems that their fellas are having some difficulty transitioning into middle-aged fashion-wear.

Although I do my best to steer clear from offering advice most of the time, I too have noticed the struggle many men have when it comes to their wardrobes.  So, in order to encourage and support my fellow mature male counterparts, I will walk you through some helpful hints, ideas, and logic that should make dressing yourself appropriately simple, easy, and comfortable.

Gentlemen – let me be clear about this.  Middle-aged fashion is ALL about comfort.  If it doesn’t feel comfortable, toss it.  You’ve complied with tight, itchy, bunchy and downright annoying clothes all your life – it’s time to liberate your body.  You deserve nothing less.

Lets begin by reviewing some of the common issues men often face when it comes to choosing and wearing clothing.

COLOUR BLINDNESS

If you’re like me, you either play golf, talk about golf or watch golf on T.V.  What do you notice most about golf attire?  Colour!  Multi-coloured pants that do not match the shirt.  White shoes no matter what the rest of the outfit looks like.  There’s a good reason for this.  You see, in nature, it is the male of the species, not the female, that has all the style and colour and pizzazz. This is natures way of creating a visual distraction that temporarily blinds or confuses other males, allowing one to ‘swoop in’ and take its rightful mate.

In golf, although there aren’t a lot of ‘mates’ out there with the guys, the basic principal is the same – you want to create a distraction with your wardrobe so that the other players can’t focus on their game.

I get a chuckle when I’m leaving the house to go golfing and my wife questions my wardrobe choices.  She’s so cute!  She doesn’t understand that the colour choice of the golf outfit is almost as important as the club choice.  In fact, if you golf like I do, its a more important choice.

When it comes to colour, gentlemen, you need to dock the dockers, burn the beige, grind up the gray, and put on the loudest, mismatched outfit you can get your hands on.  Nothing will tell the world you’re over 50 and ready to take it on, more than a bold colour pallet on your back.

WHERE DO I WEAR MY PANTS?

The debate over belt height is a contentious one, to be sure.  Because of a wardrobe malfunction on a ‘gang-banger’ in East L.A. back in the ’80’s’, kids all over the world, in an attempt to stay young, have abandoned their belts.  This has allowed their pants to continually droop down to the point where they not only look like they’ve messed themselves, they can barely walk at all.  Ironically, that’s exactly the same look you’d find in a senior’s home.

Most pants these days don’t allow for much freedom when it comes to where the waist sits on your body.  Many men with ample, trophy-sized mid sections, tend to hunker their pants below the waist, since getting them any higher would mean buying their clothes from a tent maker rather than a good men’s store.

Others are unnaturally slim, probably from a vegan lifestyle.  These people only wear clothing that has drawstrings or are made of spandex, and they ride bicycles.  Fashion is irrelevant to them.

There are some men, due to no fault of their own, perhaps due to a terrible illness or a meat allergy, have grotesquely small waists, and tend to wear their pants as high up as possible.  I assume that this is to hide an embarrassingly small mid-section.  I don’t blame them for doing this, but it isn’t a good look.

Either way, there is only one solution for all of these body types – do not tuck in your shirt.  Tucked in shirts are for uptight corporate types and people under 40.  What do you need to prove, anyway? Let it hang, gentlemen.  This negates any further conversation of where on your waist you should wear your pants – it doesn’t matter, as  long as it’s covered up.

SHIRTS

This is a real struggle for most men.  Bottom line is, wear a shirt at all times.  There are hairy, lumpy bits that the rest of the world doesn’t want to see (I’m really hoping the guy at the end of my street reads this before he works in his yard again).

Okay, so now you have to decide what kind of shirt to wear, depending on the event.  Here are some basic ground rules:

  • If you’re wearing a t-shirt you got in a case of beer, or at a concert or NASCAR event, you should only wear it to flea markets, rib eating contests, doing chores around the house, or to your mother-in-law’s home.
  • Golf shirts are the ultimate fashion ‘must-have’ for men – casual as a t-shirt, classy enough for the office.  Because of the collar, it can be worn with shorts, jeans, or even dress pants.  It’s our version of the little black dress.
  • Long-sleeve button up shirts are for serious business only, or funerals and weddings.  They don’t go with shorts, unless you’re at a really hot wedding…

Again, be sure it fits comfortably, and isn’t too short – nothing is worse than a good old beer t-shirt that doesn’t cover the beer holder gut you worked so hard on. This will also take care of the whole pant height thing too.

FOOTWEAR

I know – sandals and socks, right?  Well, it’s more complicated than that.  As a rule, if you’re wearing sandals, it’s because you’re wearing shorts, or God forbid, a Speedo, which means it’s too warm to wear socks. However, due to horrible foot fungus disfigurements or toe-nail removals, there are times when socks are not only a good idea, but a necessity in order to keep the general public from loosing their lunch as you stroll around town.

For all other purposes, slip-on shoes are the way to go.  You’ve bowed to the lace gods for far too long.  Stand up straight and slide those dogs into something that doesn’t ask anything in return.  Velcro straps are also a stylish and practical option as well, but they require bending over.  No one wants to see that.

I’ve heard that some people claim the shoes should match the belt, but I think that’s a sexual reference that I don’t understand.  Do what feels right.  If you only have a black belt, any kind of footwear is fine – please refer back to my comments on pants and shirts.

UNDERGARMENTS

It used to be simple – boxers or briefs.  For the sake of any squeamish readers or the very young, I won’t post an image on undergarments. Today, there are any number of hybrid underwear styles, shapes, materials, and colours.  This is typical fashion industry propaganda, foisted upon an unsuspecting public who are just trying to keep the ‘boys’ from going where they shouldn’t go.  Let me make it simple:

  1. In warm weather, briefs will keep things from sticking to other things, if you know what I mean
  2. In cold weather, boxers are a comfortable, breathable vacation to your buddies, who have been crammed together all summer

If you’re wondering about thongs, you’re on the wrong blog page.

With these basic principals cleared up, there is always one question that remains for the fashion-challenged mature man;  How do I know I’m dressed appropriately?

Interestingly, the rule of thumb for men is diametrically opposed to the strategy of the fairer sex.  If a lady enters a party in a beautiful dress, the most embarrassing thing that could happen, other than toilet paper stuck to her shoe, is seeing another lady in exactly the same dress.  Horrors!

For men, if you enter a party and some other man,or even better, a group of men, are dressed in exactly the same outfit, it’s a very good thing.  This confirms that you dressed correctly. Since there’s safety in numbers, you now have a brotherhood of like-minded peers in which to discuss the game, the toilet paper on that woman’s shoe, or what to do with those little shrimp tails from the buffet.

There’s also another important rule of thumb to follow when it comes to dressing for the occasion.  I call it the rule of ‘wife’.  When you’re waiting at the front door for 20 minutes with the keys and a bottle of wine in your hand, you don’t want her to come down and tell you to go and change.  This will make you the reason you’re late.

When you’re dressed and ready to go, you should give your better half a ‘once-over’ twirl on your wardrobe selection.  This accomplishes two things:

1 – it tells her that you are ready to leave, and the clock is officially ticking.

2 – it gives her a chance to review your outfit.  If she says anything along the lines of “Are you wearing that?”, you better drop the keys and dig through the closet for a new outfit.

If she asks you to do some random job around the house, like water the tropical fish, she’s stalling for time.  This is okay, because it’ll keep you busy, and it tells you that your clothing choice will not embarrass her.

I think you’ll find this blog a handy and insightful guide when it comes to the problematic world of dressing oneself.  You might want to print this off and attach it to your dresser, so you can reference it when you’re standing there in your bedroom in your underwear and socks, scratching your head about what to put on.

Oh, one last thing. If your better half scoffs at this guide, be patient.  It’s only because she has spent decades being brain-washed by the fashion establishment, with those glossy magazines and impossible to walk in clothes.  Eventually, she’ll be dressing exactly the same way as you.

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5 thoughts on “Toronto Fashion Week – a guide for middle-aged men

  1. Hmmmmm…some of the statements sound suspiciously like your real life brothers….vegan? Toenail removal and fungus? Cycling in spandex….wonder where these all came from?

    Great read Troy!

    derek

  2. Good Morning Troy
    Your Mom sends your blog to me on a regular bases and I read them with my morning coffee. I enjoy them very much and find them not only informative but they give me that morning pick me up laugh. You have a talent for writing just like my son Trevor who has just this past year published his first book called the Long Shadow of Harold Gray. Guess it must be a Bailey thing. Keep up the good work
    Your Second Cousin from up North
    Karen Bond

    • Hi, Karen.

      Thanks so much for the kind words. I don’t know how much talent is involved, but I enjoy writing these each week, and I’m thrilled that you look forward to them.

      I’ll have to look up Travis’ book – congratulations to him on getting it published.

      Regards.

    • Hi, Karen.

      Thanks so much for the kind words. I don’t know how much talent is involved, but I enjoy writing these each week, and I’m thrilled that you look forward to them.

      I’ll have to look up Travis’ book – congratulations to him on getting it published.

      Regards.

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