Would You Wear… A Dress Over Pants?




From left: Richard Nicholl runway, Rachel Bilson at the Z-Spoke by Zac Posen launch, Melissa Joan Hart in West Hollywood, Rag & Bone runway
Back in the late nineties, early 2000′s, I thought it was very stylish and interesting of me to wear a dress over pants. Unfortunately, upon further reflection, it looked dumpy and unimpressive, and certainly not flattering. However, this trend appears to be back with a vengeance, and the evidence is splattered all across the runway.
For the most part, I continue to disapprove of this trend. I find it unflattering and unnecessary – why does one need to wear a dress and pants? The ever-increasing popularity of leggings and tights has made this even more unnecessary. However, the popularity of a short dress or a tunic over a pair of slim-fitting pants (a la Rachel Bilson and Richard Nicholl’s runway above) is common and, I believe, still stylish.
As ever, the key is proportion. Although a flowing pair of pants and dress may fly on the runway, on the streets it tends to look sloppy, especially if your pants are on the less-fitted side. So ensure that one or both of your pieces is fitted. Also important is the length – a knee-length dress, a la my early teens, is not as flattering over pants as a mid-thigh number. The great thing about wearing a dress over pants instead of tights is that the dress can be shorter than you would usually feel comfortable wearing.
Check out my interpretation of the trend below.
Outfit: When It Actually Fits

Product Information: Tube Dress: Wet Seal, Skinny Jeans: farfetch, Lace Heels: Amiclubwear, Grey Boyfriend Blazer: Red Herring.
Thoughts? Feelings? Concerns?
I may try to rock an outfit like the one above, but besides that I am fairly set in my ways. No Melissa Joan Hart for me. But what about you? Would you wear this look? How would you wear it?
Let me know what you think below – sloppy or stylish?
Posted on on March 9, 2010 / Filed Under: Would You Wear? / Tags: Dress over Pants, Dresses, Melissa Joan Hart, Rachel Bilson, Rag & Bone, RIchard Nicholl, skirts, Trends












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kaley
rachel bilson looks cute, but it’s because her pants are just like leggings. you are right–proportion is definitely key!
ms
I like the dress over pants look. It works for us northern girls dealing with the cold elements.
Brittney
5 or 6 years ago, I was a “fashion don’t” for Halloween. I wore a dress over pants. My feelings about this look have not changed since then haha.
star
I like this a lot.
I wear them together quite a bit, myself.
jem
ehhh… i am not to keen on this look. i tried it once a few years ago, and looking back on it, the whole outfit was tragic. i feel like it doesn’t really flatter people that much, creating too much “bulk” of fabric and can make a persons hips look really wide (as was the case with the look i wore) and its just plain unflattering.
Josie
My style is quite a bit on the bohemian side, and I’ve worn short, flouncy dresses both over jeans and with wider linen pants for years… So, obviously, I love the look.
I do think it works best styled a bit hippie-ish though – I’m not really sure how this look would work with stilettos.
Tamara
I like the look, but I agree with the commenter above: it’s better done the hippie chic way. You can wear wedges or heels to elongate the leg, but I think the dress should be airy and flowy (though maybe cinched at the waist). Rachel’s dress looks kind of like that, and that’s why it looks so good (among other reasons, like the fitting pants, the heels, and the fact that she is tiny).
I wear this all the time in the winter, as I like making the most of my summer dresses, but I’m not sure it works for everybody…as with anything, it’s about trying it out.
chili
I agree that this trend, for the most part, should stay in the years circa 1998-2001. I could only imagine it working in, as josie said, a boho fashion, or with a VERY light dress/tunic made of cotton jersey or something like that. The pink dress above seems a little too bulky for this look.
CLC
I wear dresses over pants a fair amount…I have a fitted black american apparel racerback dress that I wear over my black or charcoal yoga pants, and it look good because the pieces are so simple. I definitely agree that the hippie/boho, or laid back approach is the best way to style it. I have a fitted short cotton floral dress I wear over regular boot cut jeans that looks neat too. I don’t like the full skirt/skinny pants look at all, why not just wear leggings? And thanks Josie for the idea, I’ll definitely have to try it with my linen pants!
Dom
I wouldn’t…. I prefer a bigger shirt and pants. A dress and pants makes you look ill-proportioned, in my opinion.
annie
If your dress and pants are like Rachel Bilson’s, then yes. If they’re like Melissa Joan Hart’s, then no. I think this look can definitely be pulled off if worn the right way.
Ana Santos
I wear dresses with skinny jeans. It’s all in the right proportion. And I always keep it casual. I wouldn’t combine pants with dresses for a formal occasion.
http://www.flickr.com/photos/anasantos/3920869318/
Rachel
With a long tunic..yes. With a dress..sloppy.
Tracy
I used to wear this all the time, fall 2006/spring 2007. Usually it was black military dress over jeans and some flats. Some of the snarky middle school kids at my volunteer job called me “Neo” as in the man from the Matrix, since he wears that huge trench coat. I was not supposed to be a compliment.
I still love that combo to this day.
Jordan
I personally love this look.
It is chic AND comfortable. If you’re rocking it like Rachel Bilson, then of course it’s going to work, but I’m not a fan of tightly fitted with tightly fitted (like the look you created above, sorry!). Definitely a hippie vibe. I’m 5’7”, but 75% of me is leg and it’s impossible to wear short dresses/tunics and have them cover my butt! So, obviously, when tights don’t even seem to be enough coverage, I treat the dress as if it were a tunic or long top. However, I can’t just do this with anything. I know I’m reiterating but these other comenters have said it all, LONG and FLOWING are key.
Jordan
Also keep in mind, ladies,
keep the jeans you pair with your dress in a darker wash, and definitely no holes. That just screams fashion causality. I find darker washes to be more flattering. Black jeans? All the better.
alana
i was gearing up to say how frumpy it looks but i love the look you put together! totally making me rethink it. this could probably work with jeggings too since you still get the jean effect without the bulkiness. hmmm i may have to do some shopping this week
Kath
I can’t do this one. The look just gives me flashbacks to freshman year of high school when girls would wear sun dresses over bootcut or flared jeans. I’m starting to understand why so many women cringe when retro looks come back…being reminded of a bad fashion trend is a bit painful!
aish
i really dnt like this trend but i really like the outfit that you put together
its a good combination of trends(nude tone dress, lace heels, boyfriend blazer etc)
i really like your outfit combo (the pics with rachel bilson n the rumway models dont look so nice)
but i will deffinately try ur combo out
good job
Breanna
I wouldn’t wear a dress over pants. But a tunic? I haven’t even notice this is some kind of a “no-no” combination (as long as the tunic is closer in lenght to a long t-shirt than a dress). I’ve been wearing my skinnies with tunics from the very beginning, since I’m not very confident when it comes to my hip areas and I prefer to keep them covered.
For the looks above though, I would wear those dresses with tights/leggins, I don’t think pants make those outfits more stylish and defninitely they do make them less flattering.
Alex
I hate this trend.
Amy
With skinny jeans? Yes. And the dress has to be above the knees!
MuslimBeauty
i love to wear dresses over skinny jeans or black leggins with heels or ballerinas, because i think short dresses or skirts are to extrem for university or school
Michelle
I *love* your interpretation of this look! It’s hot and I actually think this look works better when the pieces are slim and tailored versus the boho look which can look totally sloppy. Again, love your interpretation and I love this blog!
Rachel
The closest I’ll get to this “trend” is probably a long shirt over a pair of VERY skinny and dark jeans, like you’ve shown above. I think it’s rather unflattering to have the waistband of a pair of jeans underneath a dress, it defeats the purpose of the way that the dress is cut to skim over your body and create nice, clean lines on a lady’s silhouette. :) I say stick to a dress and some colourful leggings or tights, it’s much more flattering on 99% of all body types!
Julz
i woudn’t use it if i’m trying to put together a “red carpet outfit” or something to formal/fancy, if you knw what i mean.. but maybe for a boho-chic outfit works, with a loose dress above the knees.. i’m imagine it lol.. but definitely skinny jeans (:
Expedia.co
Thorough and concise checklist. I agree with the previous comment that it’s nice to see it all in one place for quick reference.
Maya
The *principle* of dresses-over-pants is awful to me, but that outfit is gorgeous.
Just like I have absolutely no problems with tunics over skinny jeans- that’s how I’d normally wear those. So in case of dresses, I’d only do it if I could pull it off as being a top.
Nessa N.
I’d only wear tunics with skinny pants or it will look bulky
Paulette
I’ve used it plenty of times when I have lab class… it’s practical if you don’t want to think too much about what to wear and at the same time don’t want to show legs
Jen
Racheal Bilson always looks so stylish!!!!!! Hands up if you agree!??????
Nyeasmina
since I’m muslim I have to cover my legs I sometimes where short short dresses with skinnies. I dont like it on wide leg pants it does look sloppy. i think it only works if the dresses are short and with skinnies