Ask Harry: Ian Rosen Talks Fall Footwear, Easy Transition Pieces, and the “Work From Anywhere” Wardrobe

Fall is nearly here and chillier weather is inevitable. What are the key outerwear pieces guys need this season?

Fall for me is all about layering! The days can start cool and warm up when the sun peeks out, or a nice day can turn windy and cool out of nowhere. Bottom line: it’s important to be ready. One of this season’s must-haves is a mixed-media sweater, which is typically a zip-up sweater that is much lighter than a coat but still has down padding on the front and back to keep you warm. There are a number of stylish options from Moncler that can help you fight off wearing a jacket a little bit longer. On top of that, the down vest continues to be a staple of the fall season; we’re carrying dressier options from the likes of Eleventy and Moorer along with more technical pieces from Canada Goose. Lastly, when the weather finally turns, just about every outerwear brand is featuring new, more colourful lightweight down coats.
What about fall footwear? Can’t wear sandals to the office…

You can never go wrong investing in a great pair of suede desert boots. A darker brown or navy shoe from brands like Santoni, To Boot New York, or Church’s goes great with jeans or a dressier outfit. But until it snows, you’ll find me in sneakers at least four days a week — from brands like Brunello Cucinelli, Hogan, or Tom Ford. 
For those of us who’ve ditched the office entirely, what’s the ideal “work from anywhere” wardrobe?

Patrick Assaraf designs the elevated and comfortable basics that will slowly start to take over your closet. The key investment piece for working from anywhere is the swacket, or the sweater jacket. The swacket looks as clean and tailored as a sports jacket but feels as comfortable as your favourite sweatshirt. You can get a ton of mileage wearing this no matter where your day takes you.
We’ve been in sweatpants for over a year, and now I want to wear everything at once. How should I accessorize this fall?

It’s just so exciting to be out socializing again, so you definitely want to nail those first few outfits and complement them with the right accessories.  Bracelets are a great way to show off some personality and tie an outfit together. The more casual and colourful bracelets from Pig & Hen always get compliments. For dressier outfits, reach for the wraparound bracelets from Thompson London or Robert Tateossian. 

With the hybrid workweek, we’re also seeing men look for more options in bags and backpacks. While the demand for Tumi and Montblanc bags has continued to remain strong, there are some fun tech kit options from Bellroy and Artphere that are a lot cleaner and more casual. Last tip: if you want to look smarter (and relax your eye strain), invest in a pair of blue-block glasses from Bohten or Tom Ford. They make a huge difference, especially given our increased screen time.



Since its inception, Eleventy has promoted the perfect balance of casual elegance and smart luxury. Both are rooted in the brand’s foundational values: “made in Italy” and “responsible luxury”.


Made in Italy

In Italy, we have a unique manufacturing heritage, and it’s our responsibility to protect it. This is why we have a network made up of 94 micro-enterprises selected from every region of Italy, each specialized in a particular sector of production. Through this strategy of outsourcing Italian craftsmanship, we can offer our customers all the quality and excellence of made in Italy.

Responsible Luxury

Our ambition is to help the finest Italian manufacturing tradition to surpass itself. Our collections are designed not only to satisfy the most exacting tastes, but more importantly, to ensure that an increasingly large number of people worldwide choose the value of elegance for their everyday lives. This is the objective that we set ourselves from the very start, because we are firmly convinced that the future will have room only for ethical fashion.

In today’s new norm of “business casual,” men are seeking that balance, as mentioned before, whether you’re on a Zoom call or hosting an in-person meeting. By replacing the traditional suit and tie with an Eleventy soft jacket, fine-gauge knit, and jogger pant, the gentleman has “elevated” his look without forgoing any comfort, as comfort is the new luxury.

Grey travel jacket ($1,195), exclusive at Harry Rosen
Eleventy brown suede padded fast for fall
Brown suede padded vest ($1,495), exclusive at Harry Rosen
Eleventy reversible wool coat for fall
Reversible wool coat ($2,995)
Eleventy quilted down vest for fall
Quilted down vest ($1,495)
Stretch cotton jeans ($445)