How to dress casual, yet fun with a short dress over short leggings

by Sylvia

short dress over short leggings

Readers of this site will know that I’m a fan of wearing a short dress over pants. They are also an excellent way to wear your leggings if you want to be very comfortable in your outfit or dress very casual.

I needed a very casual outfit to see my son compete at a tennis tournament. There is no point looking too overdressed on an occasion like that when everyone else is wearing shorts and t-shirts. Still, there is no need to wear those same shorts and t-shirts either, if you like to have fun with your clothes and don’t mind looking a bit different from everyone else.

casual outfit with leggings

You need to think outside the box a bit and make just a little bit of extra effort.

The outfit also had to comply with the following requirements.

It needed to be:

  • Very cool. Remember, it’s super humid and hot here in Singapore and I was going to be outside all the time.
  • Comfortable. I would be sitting on benches etc. No point in wearing something fancy or something you can’t bend in.
  • Somewhat sporty. To fit in the vibe of the event. Leggings suit the bill in my book.
  • Fun. No need to wear something boring even if you are going to a casual event.

Polkadot dress with short leggings

I almost never wear leggings. I often find them too casual and too body hugging and prefer skinny jeans or tapered trousers to leggings, which I feel create a nicer overall silhouette. But for the reasons explained above, leggings were very appropriate here.

I opted for below-the-knee leggings as these are cooler and the most flattering. (I also don’t own any long white leggings). I specifically bought these white leggings with draped knees as I find the overall look of below-the-knee leggings with these drapes more flattering.

short leggings and tunic

Finally, I added a bit of coloour (as usual) with accessories and shoes to the otherwise black, grey and white outfit. Just a bit of red makes all the difference. The graphical bag adds a little extra interest by adding some texture and a bit of pattern mixing.

And voila, an outfit that is comfortable, cool, hip, sporty, yet fun.

This kind of outfit will never become a true favorite as I favor more dressy looks nowadays, but for the occasion this seemed like a good fit. I have also taken it on my holiday as it doesn’t wrinkle and will be very comfortable on our explorations.

Do you make an effort to make your casual outfits fun and just a bit different?


1 aileen

I think you might have given me the answer to how I am going to wear a dress in the spring/summer. So many dresses are too short to wear without anything covering the knees, so this would work. I think you look great in this and love it as a style.
I don’t think it’s too casual. I think it’s quite dressy. Well, in this part of the world it would be considered dressy.
Another hit, Sylvia.

2 Sylvia

I look forward to seeing you in these looks Aileen. You wear that dress over trousers look so beautifully!

3 aileen

That’s a very nice compliment, Sylvia, many thanks.

4 Heather Fonseca

So cute! I would totally wear that whole outfit exactly as you have it. Pretty soon I’m going to have to start wearing leggings with my minis. It’s a great way to continue enjoying a shorter skirt length as we get older.

5 Sylvia

Thanks Heather. Definitely!

6 Trina Grandinetti

I think this is a an absolutely perfect outfit for the tennis match occasion. What a classy mom you are. I’m sure your son is so proud to have his fashionable mom sitting there on the bench. Thank you for sharing this fun tip with us.

7 Sylvia

He finds it all rather funny to be honest. Both him and my husband are not into fashion at all….

8 Trina Grandinetti

Sounds quite familiar, I tried for years to buy my son stylish outfits only to see him head to school in Nike shorts and t-shirts. He is now on a basketball scholarship so I’m sure he still heads to class in either Nike shorts or sweats with either a t-shirt or hoodie on top. Although, next week he is receiving an award during half time at which time I will be there, he called yesterday to ask me what I was planning on wearing. Ha, they actually do notice and care. (Or maybe he wants me in Nike shorts and t-shirt).

9 Suzanne

This is so cute! I think it is very appropriate for the event – not overdone at all. It’s a fun look and I am sure your little boy was proud to have you in the stands watching him play tennis. 🙂
I am way behind on the runway shows but yesterday I saw a lot more color and that made me happy. Marc by Marc Jacobs was fabulous! There is some buzz too about the dress over pants look – full trousers and not leggings or skinnies. Some of the editors do not like the look but it could catch on. It made me think of you.
As far as “thinking outside the box” – I may have had an electric blue streak added to my blond hair today. Yep, that might have happened. I have a big sporting event to attend at my son’s university this weekend and the girls in the salon were putting pink streaks in each others hair and I was feeling a bit adventurous —. My hubby can not stop laughing but my son thinks it is awesome and I don’t regret it. Sometimes you just have to do something wild.

10 Sylvia

How fabulous that you coloured your hair. I’m sure I would love it. I saw pictures of Helen Mirren too. Just love her!
As for the fashion shows I’m way behind, but internet connection is difficult to come by here (now typing away on my laptop in the lobby) so will have to do most of my catching up next week.

11 Greetje Kamminga

I always wanted to do that, colour my hair, partly blue. Way to go Suzanne.

12 traceyliz65

cute and very appropriate for the event!

13 Sylvia

Thanks Tracey

14 Laurie

Sylvia, I like this look on you.

15 Sam

This is a really great alternative to shorts and a t-shirt, which is a look I don’t find flattering to me. I find it difficult to find something casual but stylish as an alternative, but this it’s something I’ll definitely be trying if and when we get nice weather in the UK.

I agree with Aileen that it looks quite dressy, but in a perfectly casual way, if that makes sense!

Do you have any tips for the perfect length for cropped leggings?

16 Sylvia

Thanks Sam. I discussed this here: and will also touch upon this topic again next week.

17 Greetje Kamminga

Very stylish, very good outfit for the event and last but not least, it makes you look good. That dress shows off your figure.
Question: i always have to cover my shoulders to avoid sunburn. Did you sit in the shade?

18 Sylvia

I do the same Greetje, but I was mainly going to be in the shade this time.

19 Annette

This is a fabulous outfit for the occasion! A casual yet chic combination I’d wear when I am not in my usual dress or skirt style.
The length of your leggings is just right for summer, also mid-calf is something I like.

Lady of Style

20 Marianne

Save this outfit as well for your visit to Europe. Even in Wimbledon you would be dressed appropriately for the event. Just add sunglasses and a hat.

21 Sylvia

It would be a perfect outfit to pack as it doesn’t wrinkle!

22 Marianne

Sorry you already have your sunglasses on.

23 Nina Forrest

I love the outfit. I let my hair go all grey but colored the front purple (using temporary color from Sally’s Beauty Supply – I just brush it on after I shampoo and dry my hair, then rinse it off right away under the faucet and then let it dry). It has been so much fun. People of all ages and fashion styles stop and say “I love your purple hair”!!! Makes for great conversation.

24 Marie S

Wow sounds great! Mine is grey too. I’ll have to try it. 🙂

25 Marie S

I love this outfit Sylvia. I would love to try this if we ever get any nice weather in the UK.

26 Suzanne

Sylvia – wait until you see the Michael Kors Runway! He showed a lot of leggings – some the same length as your white ones! And he had a lot of cobalt mixed with black and white like the outfit you posted the other day. He also showed orange – on guys and girls – and camo print everything including a coat that I did not find hideous. LOL! He is probably the best American Designer for sportswear looks – real clothes that real women can wear in real life.
I also adored the De La Renta/Galliano Runway. No one does a ball gown like Mr. De La Renta. His #14 little black dress is perfection. His clothes are always classic and elegant. He paired black and brown with turquoise (#16?) and it was striking – not the outfit but the color combination. I am filing that idea away. 🙂

27 Sylvia

Yes, there were some great looks there. But I’m still underwhelmed about most of the new collections I have seen sofar. Nothing really too new and in my opinion far too many (too) wide shoulders and oversized jackets. And way too dark. I’m so over full black outfits… But yes that number 14 is delicious (I can handle black when you still see a lot of skin). I agree I like that brown turquoise combination too. Makes brown a whole lot more interesting….

28 Ofelia

This is a cute and sporty outfit that can be wear at many sporty events, well with the exception of hockey!

29 Rita

A very cute and sporty look. I’ve never thought of knee-length/below the knee leggings, except for yoga class. Great idea!

30 Nanne

You look great as always! This is even a good idea when traveling from cooler to warmer climates – wear the leggings and a cardigan on the plane and take them off when you reach your destination:)

31 Sylvia

Yes and another advantage is that both garments don’t wrinkle, so great for packing on holidays!

32 Buckle Button Zip

Love this sporty look on you and the shorter leggings really appeal to me because they might work for my proportions. Will have to try it. Thanks for the idea.
x Laura

33 Alyssa W.

Sylvia you look so darling!! Love the dress over leggings and the pops of red.


34 Highland Fashionista

Polka dots are so everywhere right now! That dress is so cute on you! Your blog is going to be financially detrimental to me, I fear…..

35 Sylvia

Oh I don’t want to responsible for too much spending. Perhaps go through the style challenge articles and make sure you make the right decisions!
Thanks for leaving your first comment on 40+Style!

36 Ann

What a great way to wear a shorter dress You look lovely, comfortable and happy! The dots are fun with the printed bag. Nice to see somewhere warm!

37 Sylvia

How lovely to ‘meet’ you Ann. Just visited your blog and love your style and haircut. Let me know if you would like me to add your blog to my 40+ community page:

38 Ann

Sure I would like my blog added to your community page. Thanks for doing your extensive blog! The jewelry of Iris Bodemer is divine.

39 Lorraine

After the success of my H&M tunic I popped into the store again the other day. They have some really cute T-shirt dresses in brights, spots and stripes which reminded me of this dress. They are short sleeves rather than sleeveless. Annoyingly I can’t seem to see them on the web site but they are £7.99 each.

40 Sylvia

Sounds like a great deal!

41 Lorraine

Yes, thinking of trying – not something I thought I could wear, but with leggings…..

42 Sue @ A Colourful Canvas

This look is over the top adorable Sylvia! But how is it that leggings this length look so right, but capris not so much? Each time I look at the photo, I see perfectly balanced proportions and yet you have red flats on, white leggings, and a dress in gray and black. I suspect that the magic of this outfit is largely intuitive…but are they any suggestions, or magic formula for leggings with a dress? And do you think it is a look for those taller than my size?

43 Sylvia

Leggings or trousers at this length don’t break up the leg line so much and does not have a shortening effect, so no need to wear heels. I like wearing short dresses (like this length) over trousers a lot, both with full length, 7/8 and knee length. As you say it’s playing with proportions. Of those 7/8 or capris are the most difficult to pull off unless they are very tight over your legs.

44 Petra

Ah, you are wearing my look! Veeery nice! To make mine dressy, I wear black tights in the same length and more of a “floaty” tunic with overlapping sheer fabrics. You look really good Sylvia and I’d like to see more of this look!

45 Sylvia

Thanks Petra. I will keep it in mind! Your variations sounds wonderful too.

46 Skokie

OMG Sylvia you look ultra chic in all your outfits. Just too good for your age. 🙂
I am in my twenties and can easily adopt most of your ideas. Thanks for the superb mix n match tips

47 Sylvia

Hi Skokie. Thanks for your feedback and kind words! Great to hear that you find my ideas inspiring for your style as well.

48 kay kerns

cute cute cute may be moving to Arizona soon === love this !

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