The London Lounge

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It depends on how much time and money you are willing to risk and what benefits you expect. If you have some tailoring venture capital you are willing to put at stake to explore alternatives to your established ways, go for the challenge.

In other areas I've learned some hard lessons that have taught me to stick to the house specialties.

This seems a situation in which to apply that rule of thumb.

As finding a young, ambitious, talented Italian tailor with a vision he has developed over years of hard work and is cultivating to take to new heights, and then asking him to stomp on the brakes and do that which he has already scorned, seems folly.

2¢

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If your not-too-young tailor has an elegant cut, I see no problem having him make you a linen suit - on the contrary. I hope it turns out much better than your source of inspiration and perhaps you might be persuaded to reconsider the colour. But what kind of flashy flair do you expect the young tailor might impart to a DB suit?