How to Style Short Shorts

9th May

I’m sure that the first thing many of us think about while pondering short shorts is how our legs look: is my skin too pale/uneven, have I exfoliated enough, or have my gams gotten enough exercise? Once we make it past those mental challenges, however, thoughts usually turn to style: how can I look chic rather than cheap in short shorts, and what is the best look for me?

How to wear short shorts

Rodeo Drive, Beverly Hills

Even over forty, I will definitely wear short shorts. I don’t believe that if a woman has relatively toned legs that age should be a factor in deciding whether or not to wear them. I do think, however, that there are times when short shorts look better than others. Observations in L.A. (short shorts mecca) recently gave me ideas on wear short shorts well – and not so well. Let’s take a look!

Here are 13 looks – from casual to dressy – which inspired me to say to myself, “Yes!” “No!” or “Maybe.”

1) Yes! – High-waisted shorts with a cropped top

I am always so excited to see a woman without super slender legs – more like my shape – looking great in something I would have never considered – like super short denim shorts.

If you are also pear-shaped, you might want to make a mental note here; notice how a high waistline draws attention to a small middle. Also, the (longish) cropped top in a hue close to that of the shorts creates a nice clean silhouette while minimalist footwear help promote a wonderfully long leg line.

how to wear short shorts

Near Santa Monica beach

2) Maybe – Although I love and advocate dressing sexy, there can be an inverse relationship between exposure and sophistication.

This isn’t exactly a fashion/style rule, but I think that in order to look stylish while “hanging out” (pun intended) in public, a little subtlety goes a long way. With short shorts, I prefer more coverage on top. Of course, beach short shorts and cleavage are definitely called for at the beach. 😉

how to wear short shorts at the beach

In defense of this woman, she seems to have come from the beach. Santa Monica

3) Yes! – Short shorts with an off-the-shoulder blouse with long sleeves is sexy and stylish!

I also do love the unexpected, like short shorts and booties.

Short shorts look that works

Rodeo Drive and Brighton, Beverly Hills

4 & 5) No and Yes – A summerweight fringe sweater can be a cool way to dress up a shorts outfit.

Note: avoid wearing denim shorts that cut into your waist, especially with a clingy t-shirt, or else tummy bulge – as seen below to the left – can be an issue. One quick fix for this is a more structured top, like, for example, one with an empire waistline which flares out at the bottom.

For women with shapely legs, a wedge heel – as seen on the woman to the right – is usually very flattering with short shorts.

How to (and not to) wear short shorts

Santa Monica and Beverly Hills

6) Maybe – Putting an edgy spin on short shorts creates an interesting look

These mauve shorts so closely match the tone of this woman’s skin that they visually lengthen her legs. My only “however” is that such short shorts, you might want to have extra toned legs.

How to wear short shorts

Santa Monica Promenade

7) Yes! – I’ll risk being called “tone-ist”; gorgeous gams make denim shorts with just a tee and sneakers look good.

Of course, this doesn’t excuse poor choices with those latter items. Converse here are fun with a casual handbag and baseball cap.

How to wear short shorts

Santa Monica Promenade

8) No! – The wrong handbag

I know how easy it is to just grab the handbag that already has all of your stuff in it – I’m totally guilty of that! – but if it clashes with your top and/or the style of the rest of your look, you might want to take the time to switch to something that fits better. In this case, it would be something more casual – maybe canvas.

How not to wear short shorts

9) Yes! – This is more like it!

All the elements of this look work together cohesively: all are casual, loose, and stylishly boho.

How to wear short shorts

Rodeo Drive, Beverly Hills

And my 4 favorites…

10) Yes! – Off-the-shoulder romper with bell sleeves

This look with lovely black booties lacing up the sides is all about style.

How to wear short shorts

Beverly Hills

11) Yes! – Patchwork-themed romper with a ruffle at the hem

Notice that rompers work for both this woman and the one above, even though they have very different frames. The metallic espadrilles here add sophistication.

How to wear short shorts

Beverly Hills

12) Yes! – White on white 

When temperatures rise, some of the coolest looks are all-white. Notice here how lace and very light grey detailing on the top and flatforms with a touch of metallic keep it oh-so-interesting.

Short shorts look in all-white

13) My favorite! A crisp white long-sleeved blouse with a double-layered pair of shorts are the ultimate in chic.

As I mentioned in my last outfit post, long sleeves in hot weather can be a super comfortable option. Again metallic footwear goes so well with dressier short shorts.

How to wear short shorts

Rodeo Drive, Beverly Hills

I hope these looks have also inspired in you some ideas on how to make short shorts work. Which look is your favorite?

XO, Janea




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15 responses to “How to Style Short Shorts”

  1. I do not like example one. I think the high waist emphasizes the width of this muse’s hips and the hemline of the short shorts immediately draws the eye to the widest part of her body, which is at the hemline. My favorite look for super casual short shorts is examples #2!

    That’s the beauty of style, everybody has their own!

    • Janea says:

      You are so right, Melissa. We all have our own sense of style, which is a good thing. ? The look of the woman’s hips in example #1 doesn’t bother me at all, but then I think that even non-slender hips are lovely. (For someone with saddlebags, however, I would not recommend the same cut.) XO

  2. Julia says:

    Love # 11!:)

  3. Gemma says:

    Great post, loved all the styles here. Gemma x

  4. Great post! 🙂
    I love the second style!


    Photogaphy & Fashion Blog

  5. Janea says:

    Thank you so much, David. That means a lot, coming from you! 🙂

  6. Even though I am 37 I still wear shorts, and I will continue. But I think the styling is very important.

    Linda, Libra, Loca: Beauty, Baby and Backpacking

  7. Love everything about this post! So cute!
    Love, Hadasah Love | Instagram @hadasahlove


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