How To Style A Short Dress and Be Confident

How To Style A Short Dress and Be Confident

I have once been embarrassed over a short dress and ever since, I have avoided it like a plague. If I am ever going to wear a short dress, I always ensure that there’s a free ride to and fro. And that the environment is one such an outfit can fly without judgmental looks.  However, if you always consider what people will say about how you look, you’d never wear outfits you love. Personally, I enjoy short dresses because it makes me feel so chic and free like I’m 16. Sometimes, if it’s a bit too revealing, I leave those for very private events and maybe wear them indoors. I have been trying different pieces and reading up on how I can style my short dresses and feel like a superstar without judging looks.

Related: How To Style A Denim Shift Dress

How To Style A Short Dress and Be Confident

#1: Where are You Going To?

It would be super inappropriate to wear a short dress for a corporate or formal event, trust me, you’d feel slightly uncomfortable. Hence, it s important to consider wear you are dressing to before picking an outfit. If you ask me, I would say places like beach, picnics, hangout with your girls, movies and girls’ home visit are the appropriate places for a short dress. These are places where everyone is literally wearing clothes that show off skin or pretty short and you can easily fit in.

#2: The Short Dress Fit

I am not a size 8 or 10, hence, I avoid extremely tight outfits because it accentuate my shape and makes me less comfortable. Aside that, if it’s too short I am open to the risk of a shorter fit at the back because of my bum. So, instead of opting for a tight short dress, I always go for one that is loose and can comfortably take all my folds and imperfection while still giving me a chic look. The more comfortable I am, the better for me.

How To Style A Short Dress and Be Confident

How To Style A Short Dress and Be Confident

Sweatshirt dress from

#3: Wear Leggings or Shorts Under Your Short Dress

The first question my partner asked me when I sent him the picture was, “How would you bend down if you had to pick something on the floor?’ It’s such a genuine and necessary question because of how short the dress is. At some point, I wanted to wear a leggings underneath the dress but I thought I would be taking away the beauty and decided against that. Rather, I opted for a short underneath for more confidence. With the short underneath, I need not worry about flashing and even felt more comfortable about bending over to pick stuffs from the floor. You can also wear leggings or sheer stockings.

Last I checked though, ladies do not bend over to pick items on the floor, rather they bend over at the knee to avoid the back coming up with the forward movement.

#4: Choose the Right Underwear

For a tight fitted short dress, it is important to opt for seamless pants or G-strings as you do not want to get called out for obvious pants lines. These ones can ruin the beauty of your dress and a lovely evening altogether. Hence, always ensure you are picking the right underwear when matching your outfits.

How To Style A Short Dress and Be Confident

How To Style A Short Dress and Be Confident

How To Style A Short Dress and Be Confident

#5: Layer Them

If you really feel the need to wear a short dress but don’t feel confident because of the length, then you should consider layering it up. You can go for a little longer kimono or jacket to take attention away from your dress.

#6: Style Your Short Dress with Flats and Comfortable Shoes

Heels has a way of making your legs appear longer than it usually is and if you are wearing heels on a short dress, it makes it appear even shorter. Also, heels can be uncomfortable and make you feel more vulnerable than you already are. Hence, wear a flat shoe or sneakers as opposed to heels for a more comfortable and confident look. I decided to do a chunky look for more comfort as I was visiting and also running a few errands.

You can also try wearing an ankle boot or a thigh-high boot to cover more skin for the extra confidence you need.

#7: Be Confident

The thing about styling any type of outfit is the confidence you exude while wearing it. It’s not enough that you’ve worn the outfit but how confident are you wearing it. It is important to consider your body type before wearing any outfit, be comfortable in it and pull it off with confidence.

How To Style A Short Dress and Be Confident

Are you a fan of short dresses and how often do you wear them? Do you think short dresses are appropriate or not? What other tip would you add to the above list?

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personal style, short dress, style blogger, style influencer, style tips, styling a short dress, styling a sweatshirt dress


  1. January 23, 2019 / 10:07 am

    I love short dresses. I wear them to casual event and when I want to wear a short dress, I build more confidence and wear it with grace.

    • Akingboye Deborah
      January 23, 2019 / 10:24 am

      That confidence itself is key before you start looking like someone who’s wearing a borrowed outfit and struggling to fit in.

  2. January 23, 2019 / 11:03 am

    I love love short dresses… preferably bodycon but I like shift dresses too

    Depending on what activities I have planned for the day, I wear them with flats or heels.

    I’ve always wanted to style short dresses with a pop socks but I’ve never had the need to.. it’s still in mind though

    … and next time your partner worries about how you’ll bend or pick stuff wearing a short dress, tell him it’s ok because you ‘squat to pick’ not ‘bend over to pick’

    *inserts a naughty comment here and runs away*🏃‍♀️🏃‍♀️

    • Akingboye Deborah
      January 23, 2019 / 11:08 am

      I still haven’t gotten round to wearing bodycon, maybe when I finally shed lots of weight, I would be able to.

      Considering your complexion, styling with a pop socks would really sit well on you. I will remember to tell him as well, lols.

      Ahahaha, just keep running away.

      • January 23, 2019 / 11:30 am

        😂😂😂 I’ll tell you what I wanted to type whenever I see you

        • Akingboye Deborah
          January 23, 2019 / 3:27 pm

          I’d be waiting.

  3. January 23, 2019 / 2:37 pm

    Great tips girl. Wearing a short dress depends on the occasion and you have to make it work for your shape in order for it to look fine. Confidence indeed is key because the moment you are not confident in a short dress everyone will see it as a bad thing.
    You look cute btw in that dress. 🙂

    Ngumabi xxo | How To Level Up Your Life

    • Akingboye Deborah
      January 23, 2019 / 3:33 pm

      Very true dear. The funniest thing was that i had a stop over at the market in this dress. At first, I was a bit worried because cat-calling but I had to actually tell myself, ‘if you give them that slightest discomfort about what you are wearing, you’d die of shame today, lols’.

      And that was it, there was zero cat-calling or strange stares whatsoever. So it sure does boil down to confidence.

      Thanks for stopping by hun, really means a lot.

      • Miss Yhucee
        January 24, 2019 / 8:22 am

        Thanks Debs.. .. I tried it this morning and I loved my look…. Ur a darling 😘

        • Akingboye Deborah
          January 24, 2019 / 9:52 am

          It’s so nice. Wish i could see a full view of it.

  4. January 24, 2019 / 10:41 pm

    You look beautiful debs! As usual and these are great tips. Even though currently, I won’t really be caught in a short dress 😂 unless there’s a leggings or hosiery underneath but I’ve worn my share of short dresses in the past! And I used to really be a fan of it cause people say I have amazing legs!

    • Akingboye Deborah
      January 25, 2019 / 8:46 am

      Ahahaha, wish i had caught you in a short dress before but I bet it would fit you pretty well even with leggings because you sure have great legs.

      Thank you Salmah

  5. Simplybami
    January 25, 2019 / 8:36 am

    The dress is beautiful. You look so good. I love wearing short dresses indoor though. I don’t think I have enough courage to wear it out. I love how chick it makes one look, but the disturbing look one gets in Lagos would definitely let you have a rethink.

    • Akingboye Deborah
      January 25, 2019 / 8:48 am

      I use to be scared too of wearing it out but what’s the point of buying clothes if you can’t wear them out.

      Lagos isn’t the only place one get stares, I think it’s everywhere especially if you keep struggling to pull it down.

      That’s why I would rather go for shift dress and be sure I am comfortable on it before buying it or leaving home.

      Thanks Bami for sharing your thoughts.

  6. January 25, 2019 / 8:44 am

    I like the dress and how you rocked it. Avoiding judgmental looks is important because one silly look can spoil your confidence and ruin your mood.

    • Akingboye Deborah
      January 25, 2019 / 8:50 am

      I am telling you Adaeze, or just one snide remark and you’d just want to go back home and never come out again.

      I think it all boils down to comfort and confidence. Never try it if you are not convinced or sure. And be very mindful of where you are wearing it to.

  7. January 30, 2019 / 6:43 pm

    Thanks for the Tips am a Tall girl so sometimes we just have to flow with this.

  8. January 30, 2019 / 6:51 pm

    Thanks Debby for these tips I used to feel shy when I wear some short dresses but thank God my confidence level shot up.

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