Skip to Main Content
Capsule Wardrobe: Ontario Armstrong (traveling to Pitti Uomo)

Capsule Wardrobe: Ontario Armstrong (traveling to Pitti Uomo)

This article, you could say, has been 15 years in the making... 

We'll start with a little nugget of internet #menswear history: in 2009 Esquire Magazine ran a contest to find the "Best-Dressed Real Man in America". It started online with a public vote, then the top 5 finalists were invited on The Today Show where the winner was announced on live tv. 

Me and Ontario Armstrong from Philadelphia were both finalists in the Top 5:

I ended up winning the contest... 

But Ontario and I were both winners because this moment gave us both the confidence and credibility to start our own menswear brands and immerse ourselves in the global - and newly connected - world of men's fashion.

Over the past 15 years I've watched from afar as Ontario has navigated brand ownership, content creation, influencer projects and now embarking on a new journey of starting an independent print publication No Chaser Magazine with fellow creative Karl-Edwin Guerre (who will be our second feature later this week!).

To give you a little more background (because there is a lot) yesterday Ontario and I had a wide-ranging conversation about the beginnings of #menswear, starting a brand, Pitti Uomo, packing, peacocking, and so much more...

Check it out here:

Watch the video interview: Dan & Ontario

As you will learn from the interview above, part of developing a global menswear publication is traveling to menswear Mecca; Pitti Uomo - where insiders, influencers, craftsmen, designers and enthusiasts congregate for a bi-annual tradeshow and celebration of all things mens's style.

This year Ontario tapped Articles of Style for a mini capsule wardrobe, for his Summer trip to Pitti Uomo in Florence (which begins. tomorrow). 

Together Ontario and I created the 8-item capsule below for his trip.

What I love about Ontario's style is that he's not a flashy dresser. He dresses with restraint, elegance and class. He's not about bold colors or patterns. He's about fit, craftsmanship, texture and longevity. 

But he's never boring. The way he puts it together is always modern, fresh and cool - even though he only buys classic items that he can wear over and over again, for years to come. 

THAT, to me, is how an experienced dresser thinks and shops.

Below are the 8 items in Ontario's capsule - along with some of the many different outfits he can create by mixing-and-matching these 8 items in different combinations.


1. Triple-Blend Jacket in Hazel

The Triple-Blend jacket is an unstructured double-breasted jacket made from a lightweight fabric that combines wool (75%), linen (20%) and silk (5%). This jacket is designed to be lightweight and breathable. The wool gives it lasting performance and smooth drape, the linen gives it texture and breathability and the silk gives it a subtle luxurious sheen.Wear it as a go-to sportcoat, or combine it with the matching trouser and vest to have the option to style it as a suit.

2. Triple-Blend Trouser in Hazel

The Triple-Blend trouser is a classic trouser made from a lightweight fabric that combines wool (75%), linen (20%) and silk (5%). This trouser is designed to be lightweight and breathable. The wool gives it lasting performance and smooth drape, the linen gives it texture and breathability and the silk gives it a subtle, luxurious sheen. Wear these as a go-to trouser, or combine them with the matching jacket and vest to have the option to style them as a suit.

3. Florence Jacket in Sunrise

The Florence jacket is a soft, light and unstructured jacket made from a beautiful fabric that combines silk (50%), linen (29%) and tropical wool (21%) rendered into a beautiful (and versatile) glenplaid pattern comprised of blue and cream. If you're looking to elevate your wardrobe with a stylish jacket that makes a statement, but is still very versatile, this is an excellent option. Pair it with trousers in navy, grey, cream, khaki, brown or olive. This one is a perfect accent to earthtones.

4. Fairmount Shacket in Forest

The Fairmount shacket is an unlined, soft and stretchy shacket (a cross between as shirt and a jacket) made from a unique waffle-knit wool fabric that has 4-way stretch for comfort and mobility. If you're looking for a go-to lightweight layering piece for easy casual style, this is an excellent option. You can dress it up (for the office or "business casual"), or wear it casually with polos & chinos or t-shirts & jeans.

5. Uno bengal stripe shirt in pale gray

The Uno bengal stripe shirt is a classic button-down shirt made from a premium long-staple cotton, updated with our famous one-piece spread collar. This is one of our most popular shirt designs, because it strikes the perfect balance between dressy (looks great with a tie and jacket) and casual (the collar is designed to stand-up and frame the face when worn open).

6. Palm Springs Pleated Trouser in Cream

The Palm Springs pleated pant is a super lightweight and breathable pant cut from a pure linen fabric. It's elegant and sophisticated while also being laidback and charming. Pair it with the matching jacket and vest to have the option to wear it as a suit.

7. Hamilton Elevated T-Shirt in Forest

The Hamilton t-shirt is not your basic t-shirt. It's thicker, sturdier and built to last the test of time thanks to our famous elevated performance fabric.

8. Myles Cashmere Polo in Ivory

The Myles is a long-sleeve polo shirt with a clean neckline made from the most beautiful Scottish cashmere. This one is soft like a cloud and will add instant style and elegance to your everyday wardrobe. 


Using only these 8 items, here are some of the outfits Ontario can create...

Everything works together in any combination (he can't make any mistakes) and he can easily (and quickly) create outfits for any occasion - from business to pleasure.

This allows him to get the most out of each item and keep a cohesive, streamlined closet.

1. Sartorial Splendor

2. Summer Cocktails

3. Business Casual

4. Easy Does it

5. Tasteful Patterns

6. Beautiful Simplicity

7. Anywhere, Anytime

More Outfit Combinations

We didn't have enough time to photograph ALL of the outfits on Ontario - above are some more combinations.


For more information, including pricing and sizing options, click here:

The Ontario Capsule

The Custom Capsule Experience

Ready to create your own capsule wardrobe?

Book a zoom call  with me to get started.

I look forward to working with you!

Yours in style,

Dan Trepanier