There is only ONE rule in fashion, and that’s to have fun with your style and enjoy the journey. Don’t take it too seriously, learn from the mistakes, and laugh a lot. Everything else is a guideline that you can take or leave at your discretion. There is no right or wrong in fashion and style. Only your own set of preferences that are subjective and personal.

In that spirit here’s a set of do’s and don’ts for skirt and dresses that my clients and friends have found helpful and somewhat empowering, and you might too:


  • Do wear skirts and dresses with diagonal hems and lines because they create a flattering visual effect.
  • Do wear skirts and dresses with casual flats and sneakers.
  • Do wear corporate skirts and dresses sans hosiery. Bare legs are just fine unless your dress code states otherwise.
  • Do wear midi skirts and dresses when you’re petite, and by all means pair them with flats.
  • Do wear casual skirts and dresses for casual wear.
  • Do wear skirts and dresses if you don’t feel good in shorts.
  • Do wear shapewear under dresses and skirts if you prefer the visual effect of the contouring. Shapewear is a lot more comfortable than it used to be.
  • Do wear skirts and dresses that aren’t black because there is style life after black.
  • Do wear dresses and skirts when you find pants and jeans hard to fit.
  • Do wear dresses over pants to create a tunic vibe.
  • Do wear skirts and dresses in Winter with hosiery, tall boots, and a coat. Throw in the thermal layers too.


  • Don’t purchase a skirt without purchasing a top to wear with it, unless you have a suitable top at home. There are too many orphaned skirts in the world.
  • Don’t purchase a beautiful dress just to cover it up with a topper because it’s sleeveless or too cold to wear for an occasion.
  • Don’t ignore an ill-fitting dress or skirt if it can be easily altered to create a perfect fit.
  • Don’t feel that you have to wear skirts and dresses with dressy heels.
  • Don’t allow skin imperfections to stop you from wearing skirts and dresses.
  • Don’t wear skirt and dress lengths that make you feel uncomfortable.
  • Don’t rule out polyester or polyester-rich skirts and dresses because they’re affordable, crease-resistant, easy to launder, robust, and can drape like a dream.
  • Don’t eliminate skirts and dresses from your style because they’re fussy. They’re not. TRY THEM.

This list is by no means exhaustive, so feel free to add your own do’s and don’t’s in the comments section. Go Team Dresses & Skirts.

Anthropologie Geometric Maxi Dress

Lane Bryant Lace Off The Shoulder Fit and Flare Dress

LOFT Plus Mixed Stripe Short Sleeve Swing Dress