Men's Tailored Fit Dress Shirts

  • Editor's pick

    Le 31

    Stretch piqué performance shirt
    Slim fit
    Innovation collection

    Can$99.00

  • Editor's pick

    Le 31

    Stretch piqué performance shirt
    Slim fit
    Innovation collection

    Can$99.00

  • Editor's pick

    Le 31

    Stretch piqué performance shirt
    Slim fit
    Innovation collection

    Can$99.00

  • Le 31

    Geo scale shirt
    Slim fit

    Can$79.00

  • Le 31

    Monochrome check shirt
    Slim fit

    Can$79.00

  • Le 31

    Flannel-like micro-jacquard shirt
    Slim fit

    Can$79.00

  • Le 31

    Tone-on-tone pattern shirt
    Slim fit

    Can$79.00

  • Le 31

    Chevron stripe shirt
    Slim fit

    Can$79.00

  • Editor's pick

    Le 31

    Minimalist stretch shirt
    Slim fit

    Can$69.00

  • Editor's pick

    Le 31

    Minimalist stretch shirt
    Slim fit

    Can$69.00

  • Editor's pick

    Le 31

    Minimalist stretch shirt
    Slim fit

    Can$69.00

  • New

    Olymp

    Black-trimmed white shirt
    Slim fit

    Can$150.00

  • New

    Olymp

    Dotted lines shirt
    Slim fit

    Can$150.00

  • New

    Olymp

    Pixel stripe shirt
    Slim fit

    Can$150.00

  • New

    Olymp

    Optical diamond shirt
    Slim fit

    Can$150.00

  • New

    Sand

    White flower coffee-coloured shirt
    Slim fit

    Can$250.00

  • Tiger of Sweden

    Farrell 5 solid shirt
    Slim fit

    Can$169.00

  • Tiger of Sweden

    Farrell 5 solid shirt
    Slim fit

    Can$169.00

  • Tiger of Sweden

    Adley textured shirt
    Slim fit

    Can$169.00

    Online only
  • New

    Tiger of Sweden

    Satine stretch shirt
    Slim fit

    Can$189.00

  • New

    Tiger of Sweden

    Light pink jacquard check shirt
    Slim fit

    Can$199.00

  • HUGO

    Contrasting foliage shirt
    Slim fit

    Can$188.00

  • HUGO

    Monogram underside solid shirt
    Slim fit

    Can$138.00

  • HUGO

    Jacquard geometry shirt
    Slim fit

    Can$158.00

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Men's Slim Fit Dress Shirts

At Simons, we offer a trendy, handpicked selection of tailored-fit shirts from renowned international brands as well as our very own private label, Le 31. What can you expect from our designs? High-quality materials, abundant colour and pattern options, fine detailing, and thoughtful added features, such as hidden buttoned point collars. 

With our Fit Finder tool, you can be confident that your shirt will fit your frame as intended. Through a series of simple steps, you will enter your height and weight, belly shape, chest shape, age, and your fit preference—tighter or looser. You can even compare sizes with brands you normally wear. At the end, we'll give you your sizing options and a compatibility rating for each. Simple.