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Fashion Challenge: Wear a Dress with Pants


Dresses worn with pants
Photo Credits: 1, 2, 3, 4

I don’t know about you, but I’m more than excited for September – fall weather means I can rock my favorite scarves, sweaters, and hats from last year and arrive at class without looking and feeling like a sweaty mess! But with temperature changes come wardrobe adjustments, and sometimes transitioning between seasons can be tough. This week’s challenge may help you fill in those awkward weeks between summer and fall.

This week, be adventurous and rock a dress with pants!

I know many of you have mixed feelings on this trend. Give the challenge a chance, though–it’s a lot easier to pull of than one might think. Think you’re ready? Then throw on your fashion thinking caps and read on for some tips for rocking a dress with pants!

Tips and Tricks for Pairing a Dress with Pants

  • It’s all about proportions. I think this trend looks best with a short dress that hits around your mid thigh. Some girls can pull off the look rocked by Jessica Alba in the picture above, but it will overwhelm most frames.
  • Simple, fitted dresses work best. A dress with a really full bottom half or lots of material and draping may not be the most flattering choice.
  • Pair a dress with jeans. Skinny jeans or jeggings will no doubt look great with most dresses, but a pair of boot cut jeans or even flares can work, too! Flared jeans look best when paired with a dress that is more fitted around its hemline.
  • Try it with other pants, too. Linen pants, clam diggers, capris, even yoga pants can look neat when styled the right way!
  • Did your favorite dress shrink? Or did you get a late growth spurt? If you have a dress that’s just a little bit too short to wear comfortably, wear it with a pair of jeans instead of leggings for a fierce look.

3 Dress-Over-Pants Outfit Ideas

Night on the Town

Dress with pants outfit 1

Dress, Heels, Jeans, Animal Print Dress, Sandals

The dresses pictured above are short–they definitely approach tunic territory! Rather than pairing these with opaque black tights, try them out with a pair of skinny jeans. It will give you a more edgy look, and might be the unexpected touch you need to set your outfit apart. Pair your look with a cute pair of shoes and wear with lots of attitude!

Hippie Chic

Dress with pants outfit 2

Pants, Dress, Sandals, Bracelet, Necklace

This looks gives off a laid back, boho-hippie vibe perfect for going to class, a concert, or a walk around your college town! Start with a pair of lightweight linen pants, and pair them with a simple tank dress. This dress by American Apparel has elastic in the waist, giving it a bit of shape. Finish with gladiator sandals, a nautical-inspired bracelet, and a pendant necklace.

Lounging Around

How to wear a dress with pants - outfit 3

Pants, Dress, Shoes, Headbands, Bracelet

So, I know this look may be a little “out there” for many of you, but hear me out–when it comes to studying or watching tv, nothing is cozier than a t-shirt and pajama pants, right? For an updated take on the loungewear uniform, swap out pajama pants for yoga pants, and pair them with this racerback dress. The dress will be fitted throughout the butt and thighs, balancing out the fullness of the yoga pants, but not so tight that it’s restraining.

Finally, throw on a pair of sneakers and a cute bracelet, and keep your hair out of your face with a couple headbands. This look is perfect for lounging in your dorm room, studying in the library, or running errands.

Rocked the Challenge? Send in Photos & Get Featured Here!

Now that you’re inspired, we want you to take the challenge and send us photos of your challenge outfit and we’ll feature them on CF!

To see your challenge pics here (along with a blurb about you and a link to your blog, if you have one), take some photos of you wearing a dress over pants, and attach them in an email to fashionchallenge AT with your name, school, blog link (if you have one), and a description of what you’re wearing. (See examples here and here!)

Can’t wait to see what you girls come up with!

What do you think?

Will you try this fashion challenge, or is it something you already do on a regular basis? How do you keep it looking fab instead of frumpy? What challenges would you like to see in the future? Sound off with a comment!

Posted on on September 2, 2010 / Filed Under: Fashion Tips / Tags: , ,

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41 Responses to “Fashion Challenge: Wear a Dress with Pants”

  1. 1
    September 2nd, 2010 at 11:14 am

    I’m still not a fan of this trend but I think some of the looks are kind of cute. I’d still rather wear comfy leggings under a dress instead of restricting jeans-but the jeggings idea might be a good compromise. But what I really loved about this post is that someone finally acknowledged that yoga parts aren’t the devil! They were cute in that look! I love yoga pants for super comfortable, casual occasions like lounging and studying.

  2. 2
    September 2nd, 2010 at 11:18 am

    Sooo, I did this all the time in middle school lol. People laughed at me but I STILL think it can look fun. It’s different, and is a great way to dress down outfits. I almost never wear jeans now, but it’s a great way to wear a dress in the winter without freezing your bum off. You can do it with high waisted skirts too. Equally fun.

    I really need to get some super tight jeans (or maybe some jeggings) so I can get in on this trend. c:

  3. 3
    September 2nd, 2010 at 11:44 am

    Most of the pics there are form 2006-2007…I think it looks outdated

  4. 4
    September 2nd, 2010 at 11:50 am

    I really can’t stand this trend. Dresses are supposed to be elegant and feminine. This just looks like a mess.

  5. 5
    September 2nd, 2010 at 11:58 am

    I could never wear a dress with wide pants. Too much puffiness. I prefer the flattering combo of tunics and skinny pants.

  6. 6
    September 2nd, 2010 at 12:08 pm

    Nicely written article. I agree with eurotrips. I feel this particular combination of layers is way too bulky. Skinny pants and tunics all the way :)

  7. 7
    September 2nd, 2010 at 12:30 pm

    I’ve been rocking the jeans and dress look sine I was probably 12. As a curvier girl, sometimes I feel like leggings -even under a dress- reveal just a little too much jiggle. Jeans are a perfect solution to this. The only thing to watch out for is the waistline of the jeans. If the beltloops, button etc. shows through the dress it looks crappy.

  8. 8
    September 2nd, 2010 at 1:07 pm

    Never been a fan of this trend. Adds too much bulk.

  9. 9
    September 2nd, 2010 at 2:38 pm

    I happen to love this trend and have been doing it for years. I was actually wearing my dark skinny jeans with a lightweight dress over it before I even read this was this article! I never thought about doing that with yoga pants though. I am going to try it. Thanks for the challenges and keep them coming!

  10. 10
    September 2nd, 2010 at 2:48 pm

    Definitely not a fan of this look. Although I think some short short dresses can be worn as tunics with leggings, I would never wear longer dresses with jeans, it’s just not a flattering shape.

  11. 11
    September 2nd, 2010 at 2:53 pm

    But… Why? I don’t understand this trend…

  12. 12
    September 2nd, 2010 at 3:31 pm

    This trend seems to pop up a bit every now and then…I just find it kind of sloppy and very mismatched looking.

  13. 13
    September 2nd, 2010 at 3:32 pm

    I don’t get this trend either. It looks messy and unflattering even on girls with great bodies (Jessica Alba’s picture is a good example). Skinny jeans or leggings do a lot better job, in my opinion. BTW, the only look above that strkies me as sleek and put together is the first, where the girl (Sienna Miller?) is wearing slim fit bottoms.

  14. 14
    September 2nd, 2010 at 5:02 pm

    Sadly, I’m not a fan either. Leggings are better :)

  15. 15
    September 2nd, 2010 at 5:08 pm

    I don’t like this most of the time- it looks bulky and mismatched too often. If the dress is short enough, though, the proportions might work out. The only time I’ve done this is with a fitted minidress I have; I wear that with pants because it’s way too short for me to consider a sufficient coverage on its own.

  16. 16
    September 2nd, 2010 at 5:17 pm

    Interesting idea, I think that SOMETIMES, with leggings and much shorter dresses it could be pulled off during winter (w/ coat and boots), but overall I just find it tacky!
    Nice post, though!

  17. 17
    September 2nd, 2010 at 5:22 pm

    not really a fan, but i’m sure some girls could pull it off.

  18. 18
    September 2nd, 2010 at 7:41 pm

    I really like this post. I’m not a fan of Jessica Alba’s look with the wide leg pants. I agree with some of the other commenters that leggings or skinny jeans look way better with dresses. I do like that I can stretch my dresses later in the year. Tt’s a great way to get more wear out of your clothes.

  19. 19
    September 3rd, 2010 at 12:43 am

    Definitely not for me. I think it looks frumpy and will add a lot of bulk/weight to my frame :( But maybe someone could pull it off…

  20. 20
    September 3rd, 2010 at 4:24 am

    I can’t follow this trend. If you can rock it go for it, I just have doubts about this look having the ability to look very fashionable. Hopefully some girl out there can prove me wrong.

  21. 21
    September 3rd, 2010 at 6:31 am

    I actually think this doesnt look out-dated, its still trendy and very cute! Expecially the clogs, it often matters on hoe you wear it. If you can make it look cute, then props to you!

  22. 22
    September 3rd, 2010 at 11:51 am

    I love this look!!!! It works wonders for me because I’m curvy and here in India I just can’t go to college wearing a dress-its not allowed! I’ve been teaming up dresses with jeans for years!! But I’d say skinny jeans look better than flares. Since I wear it to college most of the time, I pair it with lots of colorful glass bangles and cute earrings…they look very feminine and definitely pretty!!

  23. 23
    September 3rd, 2010 at 4:28 pm

    This has always been a key look for American Muslim girls who try to cover up their legs modestly (e.g. don’t wear short skirts, leggings, etc.). I learned this from my friends who wear hijab (the headscarf) in college, who have been doing it for years, regardless of the trends. We typically pair the dresses with straight leg or wide leg jeans/pants. Skinny jeans are just too body conforming, and therefore are just not modest enough.

    Sites like and provide some examples.

  24. 24
    September 3rd, 2010 at 5:55 pm

    I have been trying to pull this look off for awhile now, but I’m just never sure if it looks right… I guess I’m the one wearing it, so if it feels right, and I like it, then who cares?! I definitely think it would have to be a shorter dress and skinny jeans for me to wear it though.

    Speaking of challenges… I’m having a 30 day hair challenge on my blog (30 days, 30 hairstyles) and I would love if you would check it out and let me know if there are some improvements I could make! I love this site and would really appreciate your advice and feedback!



  25. 25
    September 3rd, 2010 at 6:05 pm

    I love, love, love this look!

    I’ve been dressing like this for years, even though it hasn’t been in fashion – I adore the boho look of it.

    IMHO, wide legged pants work just as great as skinny jeans – it all depends on the style of the dress. I would only use airy summer dresses or casual tunic-style dresses though, never anything too dressy.

  26. 26
    September 3rd, 2010 at 7:42 pm

    im still not convinced
    im sure some ppl can pull it off but its not my thing

  27. 27
    September 3rd, 2010 at 8:55 pm

    I never thought about this week’s challenge being a good option for different cultures!! I’m glad that this draws some attention to this trend, and offers it as an stylish option :)

  28. 28
    September 4th, 2010 at 12:29 am

    I really don’t like this trend :/ IMO, it looks awkward any way you put it, unless they’re SKINNY SKINNY jeans.

  29. 29
    September 6th, 2010 at 2:03 pm

    There are reasons why so many people do not like this trend. Pairing a dress with jeans doesn’t necessarily mean all kinds of dresses will go with every kind of jeans. Some dresses will look good with jeans while others might just end up looking absolutely terrible! So one basic tip to keep in mind while following this trend is to pair the right style of dress with fitted or skinny jeans. And DON’T forget to add loads of bangles(on just one hand of course) and you’re set!!!

  30. 30
    September 10th, 2010 at 1:54 am

    I don’t like my legs showing because I have very fair skin. If I do not wear tights or leggings, I have paired shorter dresses with denim. I think it is a fantastic trend if done right. I have found this style works best on mini dresses. Also I always try to cinch the waist in so I don’t look frumpy. I have also found wider leg pants to work well with this style, but I disagree with the pics above with longer dresses. I think when the dress comes down to the knees you really shouldn’t pair it with pants. When in doubt use your arms as a guide. I always pair my pants with dresses that touch just where my fingers hit my thighs.

  31. 31
    September 16th, 2010 at 11:06 pm

    I absolutely do not at all like the hippie chic look! I don’t like the pant or the dress! The accesories are cute though!

  32. 32
    September 17th, 2010 at 2:54 am

    i like lounging around bt not so much……..:0 Bt accesories r good.

  33. 33
    September 27th, 2010 at 4:09 am

    OMG! I do this all the time. I’ve been wearing this way before it became trendy. I think its cool and comfy. Plus it adds versatility to my dresses. :D

  34. 34
    October 2nd, 2010 at 9:27 pm

    I definitely love this look, but its not for me :( I’ve always been short and wearing a dress without jeans or leggings have always made me look taller. does anyone know of how shorter girls like me could rock this look?

  35. 35
    October 3rd, 2010 at 8:05 pm

    I already wear dresses with pants because it is comfortable and I do not want guys to hit on me if I go pantless.

  36. 36
    June 11th, 2011 at 2:11 pm

    wow, cool , i like that new trend
    i really need a change
    that would be cool w/ a super tight jean


    i like that

    ima get it

  37. 37
    June 12th, 2011 at 10:35 pm

    I think this is another one of those trends where not everyone can pull it off, even more so than most trends. The girl’s outfit in the second picture is cute, but Jessica Alba just looks frumpy. This trend just does not work with longer dresses. I’d say mid-thigh is the best.
    I love the article, though; it’s given me some ideas. I have a dress I got in Hawaii many years ago, and while I haven’t grown much ‘around’, I have shot up in height, most of which went to my legs, so there’s no way I can wear that dress without something under it. If I hang my arms down by my sides, the hem is practically at my wrists!
    I also agree with a lot of the above comments; bootcut/flare jeans just do not work. It’s skinny or nothing, lol!

  38. 38
    November 21st, 2011 at 7:32 pm

    I read everyone’s comments, and the best thing that I can say is that fashion is not about “trend.” Real fashion is a style, and is typically based upon an individual’s personal style. As one of the other comments explained, not everyone can “pull it off;” however, if you love the way you look after viewing yourself in the mirror, then by all means wear the style and love how you look in it. As of this fall, I have worn this look twice. Why not? It stretches my wardrobe. I’ve worn a cute short-sleeve above-the-knee dress w/a long-sleeved tee underneath, tights, and ankle boots and I was fab! In fact, I even got compliments on my outfit. I say DO YOU! Do NOT worry about the naysayers. Being an individual is what sets us apart from others! Figure out your personal style and know what looks good on you. Trying to mimic what others are wearing – which includes celebrities just makes one w/o creative ideas. Nevertheless, ideas can be grabbed – but do your best to make it your own. Lastly, when you walk with confidence and present yourself with confidence, your elevated self-esteem will be toxic —- meaning, it will be emitted to others and your fashion sense will not be questioned!

  39. 39
    December 22nd, 2013 at 12:03 pm

    Hey Girlss! I think this look is a great choice… A short dress looks great with skinny jeans! You just have to try it yourself and don’t judge other people (like me) just because they choose a trend you can’t pull off! ????

  40. 40
    November 4th, 2014 at 2:35 pm

    Enjoyed reading this article!

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