Guys, wearing shorts that look great is not that hard.  The image above depicts several shorts mistakes that we all see – dated, adolescent, sloppy, or worn in the wrong context shorts.

The good news is, shorts rules are easy:

  •  Width:  You wouldn’t wear baggy casual pants with sagging butt and giant legs, right?  Then why would you wear baggy shorts?  Gentlemen’s shorts are meant to be comfortable while being tapered and fit with the same fit preferences of your chino’s and other casual pants – from fitted/slim to tailored-not-too-tight.   Consider your silhouette as you look in the mirror – You want to avoid the width of the short being as wide, or wider than the hip and waist. 


  • Length:  Getting the perfect length on shorts is a piece of cake with a J.Hilburn Custom Short.  This link will take you to just a few options of at least 50.  Not in your price point? Try clicking on the SALE section.  This is the best way to get the fit of your shorts perfect.   If you prefer shopping for ready to wear shorts, look for options that don’t go longer than the top of your knee.  Finess the exact length by adding your personal preference as well as proportional considerations (finding the right length in shorts is what we do in a personal consultation) especially if you are short or tall.  In general, the best shorts hem landing spot is usually from 1 to 3 inches above your knee cap, or an “inseam” of about 8″. 


  • Shirt length: Don’t swamp your shorts by wearing a too-long shirt.  Your shirt length, whether button down or tee, should be at the lower end of your hips, or about the middle of your back pocket.   Any longer and you will be out of proportion. 


  • Shoes:  Ahhh, here is a critical shorts factor.  Please refer to my Tread Lightly Men’s Sandals  blog post for shoe options, but for here, the basic guidelines you want to follow are:
  • DON’T wear clunky athletic sneakers with around town shorts
  • DO wear athletic sneakers with shorts at the gym or on the track
  • DO wear low profile casual sneakers with around town shorts
  • DON’T wear flip flops of any kind with around town shorts
  • DO wear flip flops with bathing suit shorts at the beach or pool
  • DON’T wear calf high socks with shorts
  • DO wear no-show, like these for example from Mack Weldon 
  • DON’T wear shorts that are ripped – either by wear or “distressed” (rule waived if you are not yet of legal age to drink) 
  • DON’T wear shorts that have large logos or graphics or very large patterns (again, see above rule waiver) 
  • DON’T wear shorts with cargo pockets (unless you are on a mountain top or embracing your inner Dork)  🙂


In conclusion, any garment that you wear in public reinforces your personal brand.  Shorts are not an “opt-out” because they are on the casual spectrum of your wardrobe and you think it doesn’t matter.  It’s so easy to get comfortable shorts that fit and feel great – so why not?

Want help with your shorts?  That’s part of what I do! 


Ann Lindsay is Suited for Love and Style of Success

I work to make you look effortlessly confident.

Image Consulting      —       Personal Styling

Concierge Shopping        —       J.Hilburn Menswear Stylist

I bring confidence, organization, efficiency to your life. 

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