Do you consider your gams to be among your finest physical assets? Well then by all means, don’t hide them under a midi dress – at least not all the time and certainly not during this exceedingly hot summer! 

Now:

I’m not suggesting that you go around in a Daisy Duke getup. Among the short shorts I have observed this summer, I have come to the conclusion that there are definitely Dos and Don’ts when it comes to wearing short shorts. Let me share some advice I gleaned while style-watching, particularly in New York City and Milan.

Do:

Wear cuffed denim shorts. The cuff detail is minimal but adds more interest (style) and polish. It also keeps a snug hem from appearing to dig into the leg. 

how to wear short shorts
New York City

Do:

Wear your short shorts with something which adds to your style quotient. I’m talking about the star-spangled Chuck Taylors (to the left, below) or the faded denim jacket to the right of her. The muse to the far right makes cutoffs and the 90s overall-with-one-strap-down thing work! Savvy coordination – retro red headband, clean white tee, and black gladiator sandals – makes for a virtually timeless look. 

how to wear short shorts
NYC

Don’t:

  • Wear shorts which cut into your thighs.
  • Wear a crop top with regular shorts.
  • Wear a fitted top with fitted shorts – either tucked in or cropped – and unremarkable shoes.
  • Wear light-colored high-waisted shorts with a tucked-in white fitted short-sleeved tee and white sneakers. There is such thing as boringly retro, and if you have an inverted triangle body shape, your proportions might not look balanced. 
how to wear short shorts
NYC

Do:

  • Wear a messy bun with a tank in a vibrant hue, cuffed shorts, and multi-colored, sporty watch: subtly tasteful!
  • Light-colored shorts with a neat, white sleeveless top, and metallic thong sandals – a nice feminine touch – it especially works on a petite, girlish figure.
how to wear short shorts
Milan

Do:

Walk with confidence in your short shorts (or short skirt). Of course, it’s even easier in a posse! 🙂

how to wear short shorts
Milan

Do:

  • Wear patterned shorts with an untucked white tee, cool shades, black designer handbag, and black oxford sandals (love them!) 
  • Wear bright-colored shorts with an untucked white tank, stylish sneakers, and anything-but-blasé handbag.
how to wear short shorts
Milan

Do:

Play up contrast, pairing ripped cutoffs with a gauzy, flouncy, ruffled off-the-shoulder top – while matching accessories: beige hat with black border and beige sandals with black straps. 

how to wear short shorts
You may have seen this last muse in previous posts: she demonstrates so much of what is right about Milanese and shorts style.

Whether you are in New York where styles tend to be more urban, edgy, sometimes a bit gritty, or in Milan where even casual looks are wonderfully coordinated for balance, interest, and taste, short shorts can be a stylish answer to hot summer days in the city. What’s your favorite way to wear short shorts?

XO, Janea

 


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