How I Learned to Love Wearing Shorts


I used to be afraid of shorts. Maybe just now they’re coming out with the “right” length for me. Or maybe I just don’t care like I used to care on whether or not I looked good in shorts. But nowadays, there seems to be great shorts all around. Like the faux leather shorts I found at Zara, love them.  Getting comfortable in shorts has been a challenge for me over the years, which is strange because I had no problem wearing mini-skirts and mini dresses. There is something about shorts which seemed either less sophisticated or too casual. It’s completely not the case anymore, so how did I get to the point where I feel comfortable in shorts?

Not that I have “guidelines” but here are some things I’ve learned through trial and error:

  1. Select a loose fitting short. Tight shorts are great if you’re 20, and dancing in a night club. Pleats usually give you enough room to skirt the skimpy short issue.
  2. I don’t dare wear short shorts. How short? Well, if the shorts are short enough to have that discussion about thighs touching, or not touching, then they’re too short. However, I do like them to be shorter than the midway point between my knee and my hip joint.
  3. Try to find fabrics that don’t wrinkle. Denim, seersucker, polyester all tend not to wrinkle so badly. Linen shorts sound like a good idea, but trust me from my mistakes, they don’t look so great when you have those whisker wrinkles pulling up your shorts. J.Crew has also mastered the crepe, a washable fabric that doesn’t wrinkle… yes, it’s Polyester, but not your 70′s scratchy kind. I have a few elastic waist crepe pants from there that are basically like pajamas, but since they’re crepe, a lot more formal (and I can attest, perfect for traveling).
  4. Go with a more conservative shoe. These days flats are all the rage, so take advantage of that trend and wear flats with your shorts. Of course, I wear heels too with my shorts, but try to stick to a lower heel (around 3″) or an ankle boot, or a pair of pointy toe pumps. Sure, if you can rock an insane shoe with a pair of shorts, GO FOR IT. I’m just not that gal. Here I’m wearing J.Crew perforated loafers, which are amazing.
  5.  Self tanners help. Ok, so in this photo, I’ve been lax with the tanners, hence the pale. However, self-tanners do help in evening out skin tone, and making me feel more confident with my legs.
  6. Long sleeves. When it gets hot, forget about this “rule,” but when wearing shorts sometimes putting on a blazer, a sweater or something to helps to offset the feeling of nakedness.
  7. Just try on different styles until you find the right one. This is where I tend to mess up. Sometimes I shop based on my insecurities, “Don’t try on cap sleeve shirts because they make my arms look fat.” Stuff like that goes through my head. The truth is, every retailer, designer, etc. has a slightly different cut to their pieces, and you never know, the right pair of shorts could be out there, you just haven’t met them yet. Aww!

Anyway, I’ve mused on long enough about wearing shorts…

What tips do you have for overcoming the fear of shorts?

Wearing: Pleated Shorts: J.Crew • Cashmere Sweater: Opening Ceremony • Bucket Bag: MCM  • Sunglasses: Prada • Loafers: J.Crew


jennineHow I Learned to Love Wearing Shorts

Comments 12

  1. save. spend. splurge.

    I will never love shorts. I just hate them so much… I only wear them to yoga.

    1. Post
  2. ...love Maegan

    Man I used to hate them too!! I keep thinking it’s my old age that has made it okay as of late, lol, because I’m so much less harsh about how my body looks now. You look adorable.

    1. Post

      I definitely think that gentler self-dialogue is a HUGE part in feeling comfortable in shorts. Even though you’re as gorgeous as ever, which also helps. :)

  3. Ginnie

    I love shorts, but I understand that it can be tricky to find the right pair. I think when most women think of shorts, they picture tiny denim cut-offs. I’d say if you’re on the fence, start with short-ish (not super-short) and flowy… so that you’re basically halfway between shorts and a skirt. Then if you feel confident enough, try something more fitted (not tight). There’s a pair out there for everyone (really!), but it’s just like finding a pair of jeans, you have to be diligent, and that could mean trying on 30 pairs before you find the “one.” And I definitely agree with Jennine — balance the look with a flat shoe.

    1. Post

      So true, or those shorts that are suuuuper short, or low rise. OH high rise shorts also help… that’s something relatively newish in the trends of short-making. But you’re right, almost skirt light definitely is a way to ease into shorts.

  4. Jenn~The Stylish Housewife

    It’s funny, I also used to hate shorts on myself. And now I wear them non-stop. Even out for girls night out. But I think what really helped was joining Stroller Strides after I had my son. Pushing a 30lb kid in a stroller up hills has toned my legs so I feel better about them in shorts! I think you look adorable.

    XO, Jenn
    The Stylish Housewife

    1. Post

      Oh my gosh, I live in San Francisco on a steep hill, and so I’m right there with you on pushing heavy babies (mine is 23lbs right now) up the hills. It’s the best way to get rid of that baby weight! Now I just have to start working on my core. ;)

  5. LuceBuona (@LuceBuona)

    Very nice outfit picture!
    It is almost funny to read that you thought shorts weren’t very sophisticated when you look so sophisticated in them!
    I love your style and simplicity! :D

  6. Pingback: Handbag Roll Call: My 5 Favorite Bags This Summer | The Coveted®

  7. charles

    I usually prefer to wear them with tights under to mix up a fall/winter wardrobe.
    In the summer, I always make sure to be able to sit comfortable and squat/move around in them before buying because they are a skirt/dress substitute when i can’t wear one (like a concert or arcade date or going on a boat)

  8. Rini Kundu

    I LOVE shorts and would wear dressed up and down, weather permitting!! Here in England, I don’t often get the opportunity. There’s always tights I sppose.

Leave a Reply

Your email address will not be published. Required fields are marked *