How to Pair Jackets with Dresses – 26 Outfit Ideas & Tips


How to pair jackets with dresses. An outfit that might seem a little tricky at first to master (but is actually a whole lot simpler than we think) is the jacket and dress combo. Why so tricky, you might ask? Well, because we all know what it looks like when it’s done badly. A jacket of the wrong length over a thick, voluminous dress will look boxy and add unnecessary bulk to your frame. It’s easy to feel too covered up and weighed down when this pairing isn’t layered right.



So in today’s post, we are going to break down all the ways to wear a jacket with a dress and answer questions like, what jacket to wear with a maxi dress to a wedding? What are some light jackets to wear over dresses? What jacket to wear with a midi dress? And many, many more!

How to Layer Your Dresses with Jackets?

How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

From wedding guest attire to weekend looks and summer wear, a jacket with a dress is a popular style that is easy to replicate once you have the basics down. Today you’ll learn what types of shoes work best for long dresses and jackets, why a short jacket is a great option if you want to highlight your waist, when to wear a denim jacket, and much more.

What Kind of Jacket to Wear with a Dress?

Below I have curated 26 stylish ways to wear jackets with dresses, but before we check those out, let’s look at some tips and dos and don’ts to keep in mind so that you can rock this style with total confidence and fashion savvy.

  • The most popular style of jacket to wear with a dress is a tie between these two: moto biker jackets and denim jackets. There’s something about these two that really pair well with most styles of dresses, so if you are feeling unsure about what are the best jackets for dresses, start with one of these styles for guaranteed success. You can find inspiration from our earlier post on Varsity Jacket Outfits For Women.
  • To highlight your figure, consider a dress that draws in at the waist. This look works really well under a jacket or coat. If you are wearing a dress that doesn’t pull in at the waist or under the bust, consider a belt or a tie to cinch the waist.
  • If wearing a maxi dress with a jacket, always wear high heels. This will create a longer, more elongated look, which is desirable if you’re wearing a long dress. If you prefer a flat shoe, consider boots, or sneakers that have a little height to them. If wearing a summer look, you can definitely try sandals or flip-flops, but this style look works best for the beach or other summer style activities.
  • Before trying a longer style jacket, try a jacket that falls right at your hip bones or above them. If it hits below your hips, you might appear a little wider or boxier looking when wearing a dress.
  • Finally, incorporating a jacket into your look doesn’t necessarily mean you have to wear the jacket. You can tie it around the waist (particularly if you are wearing a denim jacket) or you could wear it sitting on your shoulders. Both looks are stylish and work well.

26 – Jackets to Wear With Maxi Dresses

Picking the right jacket for a maxi dress is pretty easy. Stick to a jacket length that falls no longer than your hip bones and look for one of a slimmer make. You want one that sticks closer to your figure if at all possible, and you might consider a dress that cinches in below the bust or at the waist.



25 – Jacket to Wear with Midi Dress

A sleek party look can incorporate a satin slip dress with a moto jacket. The blend of edgier pieces with the soft femininity of the dress is truly iconic and one that you can rock for a variety of occasions.

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24 – Black on Black on Black

Whether you are dressing for fall weather or winter, this black-on-black outfit is super chic and makes a serious fashion statement. A shorter leather jacket works well with a more shapeless dress. Add a beaded headband for a little flair!

23 – Animal Print Dress with Leather Jacket and Belt

Here’s another slaying outfit that utilizes the uber-popular and very stylish pairing of animal print with leather. The look is definitely edgy but it’s girlish, too, especially with the addition of some white sneakers which softens the outfit. You could definitely swap out the sneakers though, particularly if you are trying to create a sleeker look. Since animal prints are super trendy this season, do check out these Cute Animal Print Outfits for Women.

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22 – Dark Coat with White Sneakers

Perfect for those colder winter months, this long-sleeved turtleneck dress is just the thing to pair with a thick, though plain wool coat. This style coat has a draping effect and the length coordinates well with the midi-length frock. Two things to keep in mind when going for a look like this.

How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

21 – Floral Jean Jacket and Slip Dress

Instead of settling for a plain blue jean jacket (which is the most popular choice) this gal went with a white floral piece, very reminiscent of ’90s fashion, and wore it over a satin slip dress. The effect is very feminine and pretty, especially when paired with some delicate ankle-strap sandals and a woven straw bag.

20 – Pretty Spring or Summer Outfit

Similar to the previous outfit, the look has a few similar elements (like the slip dress and the denim jacket) but this lady kept the look a little more casual by wearing sneakers with the outfit and tying the dress around her waist. A half-up, half-down ‘do and a simple necklace round off the look.

19 – Footwear for a Jacket and Dress Outfit

If you keep your eye on the footwear shown in these looks, they range from sneakers to sandals to boots to flats. There is so much versatility and great options out there so try a few before deciding on what best suits your look.

18 – Little Jackets to Wear Over Dresses

Here are two examples of really cute jacket options that vary from the typical leather jacket or denim jacket options. Both feature detailing and embroidery and they pair really well with classic dresses. Think outside the box and don’t be afraid to try something out of your comfort zone.

17 – Dressy Look for Plus Size

Toss a leather jacket around your shoulders for the perfect finishing touch to any dress outfit. I love these sleek pumps that keep the outfit feeling very chic and fresh.

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16 – Chiffon Dress and Moto Jacket for Petites

I love the unexpected touch of men’s-inspired loafers in this look which brings a new element to the breezy, girly dress and the edgy jacket.

15 – Perfect Look for Fall

We tend to see a lot of black biker jackets but keep in mind there are other options out there, like this dark burgundy moto jacket, which looks totally fabulous over a white turtleneck and pinafore style dress. Finish off the ensemble with some white sneakers.

How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

14 – What Jacket to Wear with a Dress to a Wedding?

A soft brown leather jacket with some ruched sleeves is a great option for a wedding dress look. Dress up the outfit with a wide-brimmed felt hat and a sleek purse.

13 – With Wedge Heels

Here’s a great look for church or another outdoor activity on a cool day. A black shift dress paired with a denim jacket. Peep that popped collar and hoop earrings! This is a great look for a mom on the go. Here are some more fab Outfits with Denim Jackets.

How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

12 – Christmas Party Outfit

Headed to a holiday party? Add a biker jacket to your lace dress and throw on some tights to stay warm!



How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

11 – Casual Over 50 Fashion

An easy way to elevate a simple shift-dress-and-flip-flops outfit is by adding a shawl and a pair of statement earrings. It’s a laidback but chic look, perfect for dinner on the veranda on a cool night.

10 – What Color Jacket to Wear with a Red Dress to a Wedding?

Once again, we see the total versatility of a leather jacket. It pairs beautifully with this red, knee-length dress and is finished off with some strappy heels. Love it!

9 – Jacket to Wear with Dress to Wedding

Another option for wedding guest attire is to get a set. Oftentimes, a matching set of a dress and jacket, specifically created for a wedding, will look more formal and put-together than casually pairing a nice dress with an off-the-rack jacket.

8 – Jacket with a Dress for Women over 50

Another great outfit for ladies over 50 utilizes a navy blue dress belted at the waist, with the addition of a long pendant necklace. This is a great way to retain silhouette and shape without sacrificing the comfort of a jean jacket.

7 – Accessories for a Date Night Look

You can’t go wrong with a black bodycon dress, topped off with an edgy black jacket. Accessorize with bracelets, hoop earrings, and a stylish clutch.



6 – Jackets to Wear with Summer Dresses

Swap out your blue denim jacket for a white one to bring a lighter, fresher feel to your summer dress outfit. Choosing brighter, poppier colors is an easy way to get that warm-weather feeling in your look.

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5 – How to Style a Jacket with a Dress

Here’s a great flat-lay that gives us all the separate elements of a jacket with a dress look. This can help inspire you as you think about what you already have in your closet, and what you can adjust to make the look your own.

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4 – Casual Everyday Attire

This simple white dress gets leveled up with a moto jacket slung over the shoulders. You can wear booties, sandals, or sneakers with this look to finish it off.

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3 – Perfect Date Night Outfit

You just can’t go wrong with a cute dress topped off with a leather jacket. Add a thin belt to cinch the waist and some gold jewelry to accent the outfit.

How to Pair Jackets with Dresses - 26 Outfit Ideas & Tips

2 – Floral Mini Dress

Similar to the previous look, this jacket is tricked out with some cool straps and buckles, keeping it from looking plain and perfectly complementing the whimsical dress.

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1 – Deep Purple Dress

I love the richness of this frock downplayed with a rugged denim jacket. Girlish but comfortable and can be worn for just about any everyday occasion.

Frequently Asked Questions

Here are some frequently asked questions about wearing dresses with jackets so that you feel totally prepped and ready to take on the clothing pairing for yourself. Check them out.

Q. How do you style a dress and jacket?

When it comes to styling a dress and jacket, the process is pretty simple. You can choose to sport a jacket along with your dress for a complete look, or you could wear your jacket intermittently, say, going to and from an event and removing said jacket once indoors or while at the event itself. You’ll want to keep in mind the nature of the look you are going for. Wearing a denim jacket to a formal event is obviously not super appropriate. And the weather is also a factor to consider.

Once you decide on these things, the next step is picking the perfect dress and jacket combo! Consider your jacket’s length. A shorter jacket will work best with a bulky style of dress or one where you want to highlight your waist. A hip-length jacket is one of the most popular options, and this style will pair well with most if not all dresses.

Q. What do you wear over a dress when its cold?

You can wear your choice of jacket, coat, cardigan, or shawl, depending on how cold it is. Layering your clothing is a great way to stay warm while also providing you with various options. Keep in mind your overall goal for the look. Do you want a casual look? Try denim or a bomber jacket. Do you need a warm but formal look? Consider a well-cut coat in a neutral or coordinating color to your dress. For fancy events, a pretty shawl is always an option as well.

Q. What jackets to wear with summer dresses?

Summer dresses are easy to style with jackets. The most popular jacket we see styled with a summer dress is a denim jacket. They are a light material that you could easily pop on and off according to your comfort, and even tie around your waist if you are feeling too warm. The waist trick is even a styling trick, so you kill two birds with one stone. Check out outfits #20 and #18 for examples of ways to style a jacket with a summer dress.



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