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At that price point, options will be fairly limited and tailoring will be key. Suit Supply or the like
Suit supply
Indochino
Keep in mind that fabric is the biggest portion of the apparel cost bar (example below is for pants, but the principal scales), and that perfectly tailored cheap fabric => looks cheap
If you’re going with Suit Supply or Indochino, resist the temptation to save money on their “teaser rate” cheap fabrics that will cost you in terms of the first impression you will only make once.
Alternative:
1) go to a better store like Nordstrom and work with a skilled menswear expert to find an off-the-rack brand in a size that fits you well.
2) search for that brand/size online, where the selection is always significantly wider than you will find in any brick & mortar store.
3) work with a local tailor to adjust to your unique combination of measurements.
Also: unless you’re planning to go shirtless with that suit, use an online service built to help buyers find their ideal off-the-rack shirt Seller in minutes, without wasting time in stores
Just trying to be helpful. Have a great holiday
Spier and Mackay
I also heard great things about Spier and Mackey based in Toronto but don’t have a suit from them myself (I do have their wool coat which is great). Free returns on your first suit so I would give it a shot. Unless you need it urgently
Good luck getting sub $300 at SS. Tailoring alone can cost you 1/3rd. J. Crew or Banana Republic Outlets, then only get the basic (grey or blue) and then take them to a good tailor.
Would you be willing to go to consignment stores? Can pick up good deals
Consignment is hit or miss. A bunch of my analysts were talking about picking up Armani suits and getting them tailored. They were really happy I can’t personally vouch for quality
You should consider your budget to 500 and contemplate suit supply (preferred) or indochino