Style Advice / October 26th, 2015

3 Outfits to Wear This Fall | Timeless Looks for the Autumn Season

Fall. Autumn. Harvest.

Call it what you like.

The variety of names available for my favorite season is an ideal connection to an equally favorite topic of mine.

Men’s style.

It’s the options that make it great.

Autumn is truly unique based on the practical freedom it provides the stylish man. What other season can you comfortably wear a cashmere sweater and scarf without a jacket and still perfectly fit in? Stand out even…in a good way.

Autumn is a season where the dapper man can really make use of layering. We all know layering looks great when executed properly but no other season does it feel this effortless.

Let’s look at autumn’s competition.

Winter has you layering up out of necessity with style getting thrown out the window save for the few who reached the higher levels of style.

Summer makes use of layering only for the strategic man, someone with the talent to pair specific fabrics maximizing breathability and coolness. It’s possible…but a chore more than anything else.

Spring is a close second to autumn but lacks something subtle that’s a powerful advantage for fall. The earthy fall colors so symbolic of the season.

Yes, autumn is the ideal season for a man who loves style.

Sadly, fall doesn’t last very long so it’s best to take advantage of it while it’s here.

There are many outfits to wear this time of year. Some super dapper and some…. not so much.

I like to play it safe and wear timeless classics for the most part but there’s nothing wrong with adding some zing to your look. At least that’s my approach for fall.

If you’re stuck with what to wear this autumn, continue to read on. In this article, I list my 3 absolute favorite looks to sport the next time out with friends, in the office, or heck, walking your dog in the park. There’s a lot of cool colors in nature this time of year so don’t sit your ass in front of the computer all day J

The Weatherproof Outfit

Autumn sure has beautiful colors with great weather most of the time. Too bad it’s not always like this as it can get pretty wet and chilly.

No worries – this is where the weatherproof outfit comes into play.


Beige Trench Coat

The core item in this outfit is a light beige trench coat. My personal favourite is the ultra luxurious Burberry trench but you can find some good ones from Hugo Boss, Zara and other, less expensive alternatives.

Look for a trench that’s a weather-resistant cotton blend with a detachable wool collar and waist belt. The detachable wool collar provides options for cooler and warmer weather while the waist belt provides a tailored look to highlight your figure.

Here’s a cool tip – The buttons on your trench will give you a clue as to what to pair it with. My buttons of choice are a light shade of brown and will be my focus for this outfit.

Here is how to complete this look.

  • Navy Blue Trousers – The contrast this provides against the trench is striking but also pleasing to the eye.
  • White Dress Shirt – A staple (you better have a few of these in your closet already) and one that transcends all the seasons of the year. The white dress shirt on its own in this situation isn’t ideal but when you add…
  • A Light Grey Cardigan – The light grey tone is a balance between the navy blue and beige colors creating an overall earthy feel.
  • Brown Wingtips – I like wingtips in this case as it keeps your look versatile. Wingtips are not too dressy and not too casual. Match the brown with the shade of your buttons for superior coordination.

I wear this look in the fall at least once a week as it makes me feel super confident. The trench on it’s own is a worthy investment. Perhaps I will make an entire article on this in the near future. J

The Cozy Dapper Outfit

Men love the iconic look of the suit when wearing one.

Heck, you wouldn’t have to ask me twice to throw my vote in the “All men should wear suits” campaign if there ever was one.

Given I do like to spice things up from time to time, I’m going to suggest something I haven’t in this blog before.

I’m suggesting this fall, you sacrifice the buttoned up dress shirt for a well-fitted turtleneck sweater to be worn under your suit coat. At least for this specific outfit.

Whoa – I feel weird just typing that but luckily the look is anything but.

Take a look at this picture as an example. I don’t know about you but the map looks sharp in this outfit!

Suit and Turtleneck


I made this look a staple for me last fall and will continue to do so this year. If you plan on adding the cozy dapper outfit to your look (which I suggest you do!), here are some simple rules for you to consider:

  • Grey and navy suit colours work best. A black suit is too formal for a turtleneck and will just look out of place for the wrong reasons.
  • Your turtleneck should hug the body well but not be constricting. You want to limit looking bulky which could be tricky with a heavy, loose fitted sweater
  • There should only be two layers, the turtleneck and the suit jack for the same reason as the point above.
  • Try to get a contrasting color for your turtleneck. If you are wearing a grey suit, go for either a black, navy or burgundy turtleneck. You will look sharp while perfectly fitting in to the season.

Give this look a try and let me know what you think. Try not to tell me how cozy it makes you feel!

Rustic Simplicity Outfit

I work at a coffee shop a lot. I really don’t want to think too hard about what I’m wearing when in one but also don’t want to look like a slob either.

Rustic Symplicity

Looking good with minimal effort can be a challenge in some seasons but not at all in the fall.

When you want to look put together but still casual, I suggest you give the rustic simplicity outfit a try this season.

All you need is:

  • A high quality charcoal zipped sweater – Like always, something that hugs the body
  • A light blue dress shirt – The contrast with the charcoal sweater is a thing of beauty
  • A pair of khakis or chinos – Acts as both a balancer and keeping to the fall color theme.
  • Brown shoes and belt – For versatility and coordination

I guarantee you will feel super confortable and get great compliments while just sitting there sipping your pumpkin spice latte.

As I hope this article has demonstrated, looking sharp in the fall is more than possible. Sporting these 4 looks this season will not only draw positive attention to you, it will also provide you with a first hand look at what dressing stylishly in autumn is all about.

Now over to you – Which of the 4 outfits is your favorite? I look forward to your responses!