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Ask Harry: December 21

Ian Rosen answers this season’s biggest style questions.

By: Harry RosenDate: 2021-12-17

Ian Rosen, our EVP of Digital and Strategy (and Harry s grandson), is at your service, answering your most pressing sartorial questions. Have a question? DM us on Instagram @harryroseninc, and we ll answer it here next time.


What s your take on the "ugly Christmas sweater" trend?

(Aaron; Calgary, AB)

It can be tempting to jump on these trends, but let me propose a “Non-Ugly Sweater”. Let everyone else order up a cheap, itchy sweater that will only be won once and get yourself something nice that you ll actually want to wear!" Designers from Polo Ralph Lauren to Thom Browne have eye-catching styles made with fine fabrics. Make a statement but retain your dignity!


Air travel is more gruelling than ever. How can I make it more of a breeze?

(Laurent; Montreal, QC)

Being prepared is the key to making air travel more comfortable. For quick weekends away, I love PKG s Rosedale II Bag. It combines the versatility of a garment bag for my tailored pieces and the convenience of a duffel for everything else – so I never need to worry about what and how I m packing. A good Dopp kit is also essential. Bellroy s Leather Travel Case looks smart and has all the compartments you need. I like to keep mine fully stocked so I m ready to go and the drop of a hat.


Is the tie officially dead?

(Julian; Toronto, ON)

While we at Harry Rosen have been detailing the virtues of loosening up your tailored looks with fine knit polos and welters – I believe the tie still has its place. It s an extra detail that says,  I put in an effort! Not convinced? The right scarf can provide colour, flair and personality that a tie would provide. Protect yourself from the chill and from looking dull.


Remembering how to dress after all this time at home is a bit of a minefield. If I were to invest in one item of clothing this season, what would you recommend?

(Albert; Vancouver, BC)

An overshirt is, without a double one of my go-tos right now. It s a great alternative to a more formal sport jacket, and it can double as outerwear on warmer days – making it one of the more versatile pieces you can own (especially if you re trying to hit that cost-per-wear sweet pot). ZEGNA s Cashmere overshirt is soft, elegant and pairs well with more formal trousers, while both Diesel and Polo Ralph Lauren make hearty corduroy styles for more casual settings.


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