I Will Never Wear a Business Suit Again

Buying a $1600 suit that I took home and never wore changed me, and the uncommon lesson may do the same for you too.

Tim Denning
The Startup
Published in
5 min readDec 24, 2019

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Illustration by rudidewet.com

Yesterday, I picked up a brand new tailored suit that was made to measure. This is not the first time either.

Since 2011, I have been buying tailored suits to wear to work and have not once been happy with any of them without understanding why.

The reason I order tailored suits is that I’m a six-foot dude with big ears, strange measurements, a slim waist, and one odd-shaped rib that sticks out and looks terrible in a suit. You see my dilemma? (The current tailor also pointed out that I have one arm longer than the other and uneven shoulders — so basically I’m a cyclops).

At the start of the tailoring process, the shop owner asked me where I’d been before. He wanted my history with tailored business suits and I didn’t realize I had such a long list of fashion tragedies.

There was the suit from a bespoke tailor in the alley.

There was the suit from the online-only store of broken dreams that made me look thinner than an electrical wire.

There was the very high-priced suit from the man with the office you can never find in a skyscraper.

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Tim Denning
The Startup

Aussie Blogger with 1B+ views that made me 7-figures — Get my free email course: https://timdenning.com/1k-mb