The Wardrobe Code - Be Yourself

Shorts: How to Buy the Most Dreaded Garment of All Time

If there is one garment my clients have the most confusion over, it’s shorts. It’s a garment we have a complicated relationship with for many reasons.

The first reason shorts are universally loathed is that buying them wasn’t always such a hassle. In our 20s, it was a no-brainer. But buying shorts in your 30s, 40s and beyond is just painful. And it’s this change in our relationship with shorts that is so frustrating. What was once a friendly garment is now dreaded foe.

Second, wearing shorts forces us to expose a part of our bodies that is a notorious problem zone – the thighs. I mean, do I even need to explain why the idea of this makes us cringe? I don’t think I do – moving on …

Finally, we run into the problem of comfort. Shorts are basically pants without the legs (and, as it happens, pants are also a tough item for clients to buy). But, without the weight of the legs weighing down the garment, it causes a lot of emphasis between the legs. So, not only are we exposing our thighs (ugh), but we’re wearing a garment that may be tighter around the crotch and rump than we’re used to.

So to get over our hang-ups about shorts, let’s tackle these problems one at a time.

If you feel like your thighs just aren’t what they used to be, I totally get it. Honestly, everyone can relate to that. But, summer is coming, and we all know it’s going to be really freaking hot. Everybody has thighs, and you need to wear shorts in the summer to be cool.

Let me tell you something about your legs: they need to get out and they need to be seen.

Oh, and, summertime called. It said, “hey girl, you’re hot.” So, there.

Okay, now for the comfort part of this.

Maybe it’s possible that, if you hate shorts, you’ve just been buying the wrong style for yourself. A lot of women somehow feel like they’re limited to chino shorts or denim shorts – but that’s just not the case. Shorts come in all sizes, styles, materials and cuts. Also, the very last thing you need to be worried about when buying shorts is, “what will I wear these with?!” and instead be focused on 1.) if you like them and 2.) how they fit.

Number 1 rule of shopping: if it doesn’t fit amazingly, the problem isn’t with you – it’s just the wrong garment.

Tattoo that on your forehead if necessary. An ill-fitting garment – regardless of whatever size or brand label is on it – must fit impeccably. If not, pass.

Since it’s only just spring, you’ve got some time to find your best summer shorts styles. My best advice is to search high and low. Those regular brands you rely on? Fuggetaboutem. You need to branch out and find something new. I’m going to give you some resources below, but it’s up to you to find which brands and retailers work the best for you. So, even if you didn’t plan on shopping for shorts today, go ahead and do a little window shopping.


How to wear shorts

SELECTED long shirt
$96 –

Jigsaw striped top
$58 –

River Island racerback tank
$26 –

Alice Olivia top

Topshop top

$91 –

Monsoon summer shorts

Naf Naf shorts
$91 –

Zara shoes

Old Navy nude sandals

Mango long strap purse
$82 –

Monsoon brown purse

Coast envelope clutch
$58 –

River Island cuff bracelet
$16 –

Monsoon black ring

Stetson straw hat


  1. Have you created a Pinterest board for Plus size shorts? I can’t remember the last time I wore shorts. I am fairly good at dressing my body type but I cannot find a pair of shorts that works. I gave up and just went with dresses :-)


  2. TARNYA COOK says:

    Love that you have featured an Australia retailer. Good on you!

    • Nicole Longstreath says:

      I just think there is so much more selection than just here in the States, y’know! I probably learned that working with you ;)

  3. I haven’t worn shorts in years because of all the reasons your post highlights. After many “tries” I decided to wear what looks good and flattering, which is wide leg pants. I’m not against giving it another go, however. There are many new styles, cut and fit since my last attempt. I’ll keep you posted. Thanks Nicole.

  4. I always by shorts that hit at the knee. They are office appropriate (if you work at a casual type office) and hide those troublesome thighs. BUT this year, I’ve decided to venture in to a couple of pairs of mid thigh length shorts since I no longer work at an office. Will I be brave enough to flash my pasty white 40 year old gams??? I hope so.


  5. Kristina Brzezinski says:

    Love this post! I’ve always gotten around my shorts dilemma by wearing lots of skirts and dresses. Your post has me rethinking my game plan – I may have to get some shorts this summer!

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