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How to Wear Jackets Over Dresses

A few weeks ago I posted about layering underneath dresses. Today I’m going to do a first installment on layering over dresses. The sky’s the limit, from jackets, cardigans, blouses and shirts, to coats and even other dresses. Today we’re going to tackle jackets.

It’s all about finding the right combination of two variables:

  1. The silhouette of the dress
  2. The length of the jacket

The following guidelines are by no means hard and fast rules and I frequently see them being broken successfully by stylishly creative and daring ladies who understand how to balance out proportions. But it’s a good place to start if you’re new to wearing jackets over dresses.

Tailored cropped jackets work extremely well

Wearing a really short jacket over a fitted, fit-and-flare, A-line or sack dress is virtually flop proof. By cropped I mean that the length of the jacket hits you on or above your natural waistline. Think of cheeky styles like shrunken blazers, biker jackets, Chanel jackets, boleros, short tuxedo jackets and denim jackets. Extra short retro trapeze jackets and faux fur shrugs work well too. The length of the dress can be either a little below the knee, on the knee, or shorter. Keeping the jacket un-buttoned or un-zipped creates a vertical line down the front of the body, which is very flattering.

These pictures illustrate my points nicely.

Regular length blazers require a little more thought

A classic blazer layered over a fitted knee length sheath dress is ideal for a formal, reasonably conservative, professional work setting. But if you’re looking for a more playful outfit, try combining a shorter dress with a boyfriend blazer or hip length tuxedo jacket. I’ve found that layering longer jackets over dresses works best with form fitting or sack dresses. The proportions don’t work as well over A-line or fit-and-flare frocks unless you belt the layers at the waist. Scrunch up the sleeves for textural outfit interest.

These pictures illustrate my points nicely.

Layering knee-length trench coats and wool coats over any style of knee length or shorter frock is a no-brainer even though you’ll usually take those off inside. Shorter wool coats and trenches can work too, but they never seem to look quite as good as when the coats are as long as the dresses themselves. To my eye anyway.

If you have further questions on how to layer jackets over dresses, please ask away in the comments below. Never done it before? Start experimenting to get more mileage from your wardrobe. Any excuse to wear our beloved frocks for more of the year!

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46 Comments on...
How to Wear Jackets Over Dresses

So pleased you’ve posted about this. I wear A-line and fit and flare dresses mostly and was coming to the conclusion that I just couldn’t wear a longer jacket with them. The point about the longer jacket working best over form-fitting dresses is obvious now you mention it, but I’d never have thought of belting over my A-line/fit and flare dresses. I will be trying this this week!

Yay! I will be eating this series up!

I’ve spent the past year getting accustomed to pairing jackets and dresses properly, and now I’m never looking back!! I’m sure these guidelines will be helpful to new readers as they were for me.
Now I want to pair my relatively straight polka dot dress with my new grey bf blazer. :)

Awesome post. I’m not sure if I’ll be experimenting that much myself (not a dress fan), but I’ll gladly follow others! (I know, I know, I haven’t found the right dress yet LOL)

I have a question about cropped jackets. I’m tall (almost 6 feet), and I often feel that cropped jackets look weird on me…like they are too small. I don’t know if the proportions are just bad for me or if it’s not hitting me at the right place. Any suggestions?

Great post, Angie.

I’m ready to experiment and am on the hunt for dresses to flatter my hourglass shape. Still seeking the PERFECT denim jacket.

Since I don’t often wear dresses, I’ll be stepping out of my comfort zone.
Which is exciting!

I used to do this long time ago when I wore more dresses.. now i’ve forgotten how… LOL. Anyhow, same rules apply with cardigans?

What about the necklines? A clean crew/Vneck/cowl seems easier, what about those asymmetrical necklines, they seem trickier?

Great info! Is a jacket’s length determined by the front of the jacket? I ask because I have several jackets that are actually longer in the front and more cropped in the back. Are there special rules for this case?

How did you know I needed this information? Great and straight to the point advice.

Hmm, this is good food for thought, and the photos are helpful.

Angie, what alternative would you suggest for someone like me who is very short waisted and large busted? It’s just about impossible for me to wear a dress that hits above my natural waist unless it’s a bolero style jacket, which I don’t really like.

For example, I’ve worn my two moto jackets often with dresses (see this, this, and this for example) but though they are slightly cropped, on the proportions of my body they look like longer jackets than they really are. Is this a problem?

Oh, this will be a great series with the kind of step-by-step instructions and visuals I need. The definition of a cropped jacket is SO helpful, as I’ve wondered about that.

Loved the post! I was just asking this question to myself!

This will be a very valuable series. It makes such sense when you spell it out and illustrate with the visuals.
I was amused by the jean jacket pictured with its frayed bottom and am tempted to just cut off the bottom of a too-long jean jacket. Maybe that look is best left to younger women.

Finding a jacket that hits on or above *my* natural waist? Fat chance. I have probably the worst combination of proportions to accomplish this look successfully. Big bust, freakishly short waist, and petite all at once. For a jacket to hit at or above my natural waist, it would have to be maybe 2″ long–and then of course it tents out awkwardly at my chest.

All of my jackets except my denim jacket are hip length. They’re not meant to be but they are. Petite sizes don’t work because they are usually even narrower through the chest and the sleeves are too short.

I wear jackets over dresses a lot because I get cold and it’s practical, but I never feel great doing it. Having a large bust OR a short waist would probably be easier, but having both is the kiss of death.

My BF blazer seems to be too big for me now, so I’d like to find a new one. That might be easier for me even if it’s trickier for most people.

I am going to really enjoy this series. Already great advice here and more to come I’m sure. Having the visuals helps a lot too. Now I know WHY some of my previous attempts to layer jackets with dresses didn’t work.

Yippee! Great post. Finding that sweet spot is tricky, but these photos illustrate the magic that happens when you hit it. :) Thanks Angie!

Love this post. I want to wear my dresses more and this is the perfect way.

LOVE this! Thanks Angie! Is there a way to save a blog as a favorite? This will be great for me! The jacket will help the love handle bits hide better! Can’t wait to try it and posts pics! I think I had forgotten about this!!!

I love dresses. I love jackets. How perfect! I usually wear cardigans over dresses, but since I’m on team jacket I really need to eat this up. I can see a try on session in my near future.

I was wondering why I always felt “off” in my jacket-over-dress outfits! Armed with this information…maybe I am now brave enough to try it again!

This is so helpful! I love the look of cropped style jackets with dresses. This isn’t my best look, however, because I am so broad shouldered and larger in the chest so I end up feeling off balance. The longer style jackets with dresses is probably a better option for me but I have yet to give that a whirl. This post will serve as inspiration to try! Thanks, Angie!

Thunalata, Barbara, Debbie and Lisa, I look forward to your experiments.

Maya, Maya, Maya. You are naughty sometimes! You can be awfully negative about a particular item or combination but wear it to perfection later – and love the look. All you need to do is wear your cropped jackets slightly longer when you layer them over frocks – which is what Kari has demonstrated. Because of the size of your bust and short-waisted bodies, your sweet spot is a little below the waist. Kari, thanks for chiming in! You instinctively balanced out your proportions. Also Maya, because you wear short hemlines so well, I love the idea of a longer jacket layered over dresses for your style. Need a better fitting BF jacket for sure.

Patience, no special rules that I can think of. Happily wear your cropped jackets over dresses.

Leslie, you *might* look better with a slightly longer cropped jacket – read just past the waist. Although I have 6ft clients who look great with cropped jackets layered over dresses. They look really good layering longer blazers over dresses too. Carole, you should definately try that.

Cloud 9, we will get to cardigans :-) . Some dress necklines don’t work with jackets – like the 3D cowl variety. It’s best to layer under those and top it off with a coat.

Very helpful post, thank you. I love wearing cropped jackets over dresses and do that a lot. I’m intrigued by the other section with the longer blazers. I’ve shied away from this, thinking it might look frumpy or just not flattering on me. But I really love the middle picture with the very nipped and buttoned blazer. That’s something I can see myself trying. I might also experiment with belting a blazer over a dress, what do you think about that? (I just overall feel better with some waist definition, I find it balances me out better.)

What do we think about belting an unbuttoned jacket the way many people do with cardigans? I have rather bad luck with jackets and have a couple that pull a little when buttoned, yet when open they flap around unflatteringly and make me look like I have a giant thick torso.

Fantastic tips Angie,

I ordered a new cropped military jacket this weekend so I’m rather pleased to see this appears to be the easiest shape to layer over a dress.

I also love how a blazer helps me feel more comfortable wearing a slightly shorter hemline.

I will keep my eyes primed for the next installment.

Antje, I love the idea of belting a longer blazer over a dress. I do that from time to time too.

Linda, sounds like a good idea to me!

I am 5′ 8″, thin, very long-waisted, and pear-shaped. My waist is very tiny, but I’ve got a J-Lo butt. When I wear cropped jackets, I fear I’m over-accentuating my long waist and butt – most dresses don’t really hit my waist in the right place anyway, it’s like I’m wearing empire dresses all the time. But big jackets make me feel shapeless and I think I look like a little girl lost in oversized clothes. I really want to do this layering thing with the jackets, but not sure how best to pull it off with my body shape. What do you think?

I am interested to see what you recommend when you get to cardigans over dresses. I’ve tried it and it’s a mostly frumptastic look for me. I tend to wear cardigans with shirts, and I just don’t layer over dresses for the most part.

I meant to say, I tend to wear cardigans with sKirts. :)

I can never seem to find a blazer that fits well. If I ever get to go shopping with you, Angie, finding the right blazer will be the first item on our agenda.

This is a great post and very much needed for me right now. (Not surprising since you always find the best topics!) I’m trying to wrap my head around blazers and dresses. Somehow doesn’t seem to work for me. I’ll put some pictures up soon.

Well, this is an incredibly helpful post, Angie. NO WONDER I can’t get jackets over dresses to work in my mind without looking dowdy — I’ve been focusing on the wrong kind of dress with the wrong kind of jacket.

Lightbulb! :)

This post is a real eye opener to me so thank you very much Angie for sharing these guidlines.
I was very confused about this before your blog post. Did I luck out and get it right here, or no?
http://i477.photobucket.com/al.....0_1735.jpg
There is really no shape to this jacket, perhaps it was a bad choice. When I bought it I was thinking over sized boyfriend jacket.
Thank you

http://i477.photobucket.com/al.....0_1704.jpg

It’s me again wondering if this proportion could be better, by a more cropped jacket?

Kristie, cropped jackets and empire cuts can visually lengthen the legline – which is a good thing. Perhaps its in the silhouette of the dress? Have you tried adding heels?

April, glad the penny dropped!

San, in outfit #1 that’s a beautiful jacket and the ensemble is knock-out gorgeous. You’re wearing a voluminous jacket over a short hemline which is precisely what the guideline suggests. You made the look appropriate by adding leggings. Perfect :-) . In outfit #2, a cropped jacket would probably have looked a little cheekier, but that’s still a lovely outfit.

Mamark, what style of cardigan are you layering over dresses? Have you tried cascading cardigans?

Oh, GOOD – I’m in love with both of these jackets, so I’d hate to think that I had been wearing them poorly with dresses for all of this time. Whew! I still admire the “cheekier” look of a very cropped jacket, like your Diesel denim jacket, but the look is just going to be different on my body.

The denim jacket is slightly shorter than the cream jacket, but the difference is just enough that the denim jacket is easier to pair with skirts and dresses, whereas the cream jacket tends to be a bit more challenging. (Which is partly why I’d love to find a cropped chestnut jacket to throw into the mix someday.)

I’m dreadful at pairing dresses and jackets but really, really want to learn how. Thx for this guide!

I love wearing boyfriend blazers over shorter dresses.

Love the idea – just haven’t found the right cropped jacket that hits right at the sweet spot to wear with dresses. I have been sticking with cardis but like the more formal look that a jacket would bring to the outfit. I used to wear a long BF blazer with my short dresses back in the 90′s – loved that look!

thank you for this post – i was just trying to find a way to wear my sleeveless dress on a cold fall day.

Can’t say the boyfriend blazer over dresses is my favorite look….

I recently paired a dress with a blazer, was so very proud of myself! I had an above knee black/cream/purple dress from Kohls. Paired it with a fitted blazer with scrunched sleeves, black hose and boots. It’s going to be my favorite outfit this winter.

I have jackets of various lengths…and I am slowly collecting a respectable number of dresses. Since winter is pretty much upon us, looks like its time to put the two together and see what happens :)

Thanks for the tips Angie!

Angie, I don’t know if it’s too late to respond to you on this thread. As far as cardigans over dresses, the only two combinations I’ve found that I thought looked OK were : a sleeveless dress with a fuller skirt, worn with a cardigan that is high hip length with belt at the waist (sort of a Michele Obama look), and then a straight dress worn with a flowy long cardigan almost as long as the dress.

For most dresses, or at least the ones I have, the standard cardigan seems to make them look rather schoolmarm-ish, like I should also have extra kleenex tucked into the band of my watch. (Miss you, Grandma!)

Thanks for chiming back in, Mamark. It’s not too late at all! It sounds like you have found great dress and cardigan combinations which aren’t “Mumsy”. A tunic cascading cardigan over a sheath dress looks fabulous – so does a long BF cardigan belted UNDER the cardigan. I really like short cropped cardigans over dresses too, but then worn un-buttoned and with a V-neckline. Does that make sense?

I absolutely adore these types of posts! SO helpful. Can’t wait for the next installments in the series.

[...] like to layer jackets and cardigans over my short sheath dresses. Sometimes my layered creations are modern classic and [...]

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