How to Style Shorts | EP 83

Our Fashion Friends wanted to know: How does a woman of a certain age wear shorts? It’s too cold in the Northeast; it’s spring in the South. How does a girl style shorts – and more importantly, should she?

Your favorite personal stylist Holly Katz recently received a styling request (who even knew that was a thing, but it is now!!) from a dedicated fashion friend – and we are here to answer it: How To Wear Shorts?

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Obviously we all ‘know’ how to wear shorts. You put one foot in, you put the other foot in… But at a certain point in a woman’s life, or in a specific season, are shorts a Fashion Crime or not? 

Well, it depends. Like many women, Holly was a bit self-conscious about her legs and showing them off in shorts until HER personal stylist, and our fairy gay mother, Nolan Meader told her she was being RIDICULOUS. There are many ways to wear this very stylish and comfortable item that can work for all ages, all body types and all seasons.

What Holly loves about shorts is that they can be super casual or super dressy, depending on how you coordinate everything together. The type of shoes, accessories, and legwear you add to the mix can make all the difference. And yes, you can totally wear shorts in the winter and year ‘round.

Now before we go any further, everything we are talking about on this episode has been posted on Holly’s Pinterest board called “Holly’s Hot Picks, Spring Shorts.” 

To help visualize this conversation, go to

What are the different types of shorts? 

If this is a trend you would like to try, we always have to go back to the drawing board and figure out what your body type is – and what type of shorts will look best on you. The type of shorts that will look best on you will probably not look best on someone else.

  • Denim shorts
  • High-waisted shorts
  • Bermuda shorts, which are longer 
  • Linen, silk or fine-knit shorts
  • Work-out shorts
  • High-rise shorts
  • And the list goes on and on

Which shorts are right for you? 

Here is your free fashion tip: Short-shorts are a Fashion Crime for most humans.  Short-shorts are NOT appropriate for anyone, unless you are 6-feet tall and 19 years old. Write this down for anyone who might need to know this.

How to style shorts so you can wear them year-round:

  • Find shorts that fit your body type, and a length that accentuates your legs.
  • High-waisted shorts or shorts with a belt to help draw your waistline in.
  • Add a short jacket, a ‘shacket,’ a cardigan or a kimono to dress up your shorts.
  • Add a heel or boot to give your legs length.
  • Wear very on-trend stockings that are opaque for winter, or with patterns to hide you flaws. We recommend our BFFF Vienne Milano stockings to add sophisticated style to any short.
  • Wear a chunky sweater or sweatshirt over shorts in the winter. Try our BFFF tie-dye designer for super fun sweatshirt ideas at
  • Wear a glam bodysuit under shorts to dress them up.
  • Accessorize with statement jewelry or mixed-metal jewelry. See our BFFF Criscara Jewelry for layering ideas and truly unique and fun pieces.
  • Choose the price point and quality of fabric you need to look your best. Linen is lovely, until it shows every bit of your bumps and cellulite. Faux-leather is on-trend, very forgiving and totally comfortable!
  • Wear denim shorts – if you must – over your swimsuit at the beach. Very appropriate and practical.


Don’t be afraid of your legs. As Holly always says, “The first step is awareness.”  Know your body type. Dress for the season. Accessorize. Cover your butt. 

Do you have fashion questions? Drop us a DM on social at

Do you need help with your personal style? Then you need Holly! She is the best fashion friend you never knew you needed.  She is happy to help clean out your closet, help you shop, and ultimately make fashion your friend, not your enemy. Send her email at


“The best fashion friend you never knew you needed”

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