Ah, a dress over pants…are you a fan? I remember this being pretty popular in the 2000s but then it seemed to fall out of trend. I’ve seen it pop back up here and there over the past few years.

I like it, whether or not it’s “on trend”. I’ve done it myself quite a few times recently…

I definitely think it’s a fun way to get more wear out of pieces in your wardrobe. And if you’re like me, you want to get as many wears as possible out of your clothes. My goal is to get at least 30 wears out of each item, and hopefully many more. While I know they all may not make it to this milestone, I am hopeful that the majority of them will.

And wearing a dress over pants is obviously perfect for transitioning lighter pieces from the warmer months of summer into the cooler temps of fall and winter.

Not that shopping is ever at the top of my priority list, but it definitely isn’t at this particular moment in time. So, in honor of that, I thought it might be useful to put together a styling post on how to wear a dress over pants. Sometimes just trying something that you wouldn’t normally wear is enough to liven things up a bit.

There are a few things to consider when styling a dress over pants:

1. How do you choose the right pieces to wear together without it feeling too bulky?
2. What about proportions?
3. Is mixing color or prints okay, or should you keep it neutral?
4. What shoes should you choose?

To make this post as beneficial as possible, I have styled some dress over pants look for both warm and cold weather. I hope that you are able to use a few of these looks to think of some items in your wardrobe that you can style!

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1. How do you choose the right pieces to wear together without it feeling too bulky?

I think that the whole dress over pants idea can go horribly wrong if the pieces that you choose are too bulky, especially when trying this combination in the summer. Too much bulk and the outfit can feel uncomfortable!

Warm Weather

One of my main goals with this post was to show how to style a dress over a pair of my jeans.

For warm weather, I chose the lightest wash jeans that I own. I love the raw hem and the slit at the bottom, both of which I made. Check out this post if you’re wanting to add a raw hem to any of your jeans.

I decided to add a tercel slip dress over top. Tencel is a very light fabric that has a great “slip”. It drapes over fabric nicely and because it is silky, it doesn’t get held up on the jeans. Tencel and silk are some of the best fabrics when it comes to layering multiple items.

I also love how this dress has a slit on either side, complimenting the side slits on the jeans. It’s the little details like this that I think make an outfit feel more creative and fun!

I added a pair of cream clogs and a matching leather bucket bag to complete this look for warm weather.

Cold Weather

In order to get the most wears as possible from my clothing, I like to wear them over multiple seasons. And with the right layering, I find that it’s pretty easy to do!

I couldn’t do a cold weather styling post and not include this cashmere sweater. It’s probably one of my most favorite purchases from last winter. It’s so soft and it’s perfectly oversized.

I like how it’s long but that a lot of the slip dress is visible underneath. It slides nicely over the dress and I like how the tones of each piece go well together.

I added my brown suede boot since they’re one of my cold weather staples and I would add a matching bag to this outfit to head out.

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\\ Outfit details //

• Agolde Jamie Jeans (purchased secondhand via Ebay fall 2018)
• Eileen Fisher Tencel Slip Dress (purchased summer 2019)
• Eileen Fisher Cashmere Sweater (purchased winter 2019)
• Sandgrens Victoria Clogs (gifted fall 2019)
• Free People Suede Boots (thrifted locally spring 2019)
• Marc by Marc Jacobs handbag (thrifted locally summer 2019)

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2. What about proportions?

When it comes to the proportions of a dress over pants outfit, I prefer to wear pants that are slightly more fitted under my dresses. They don’t have to be super tight such as leggings (which also work well). However, a pair that is a little more tailored gives a really nice silhouette.

Warm Weather

For this outfit, I chose to wear a pair of leather pants under a silk dress. This look is definitely a little more dressy. It’s something that I would wear out for a date with my husband or for drinks with my girlfriends.

This particular dress is fitted on top but loose and flowy on the bottom, which gives it a soft and feminine vibe. But then you get to the leather pants, and it’s like HELLO rocker chic.

I decided to add a pair of pretty slingbacks and a simple grey clutch. Putting my hair up in a bun allows me to show off the pretty details of the dress neckline and shoulders.

Cold Weather

I love the silhouette that a long cardigan over a dress makes. For this outfit, I added a long grey cardigan that I’ve had in my wardrobe for years. It’s a really great layering piece and I think that it’s perfect over this dress.

I added a fun grey handbag and my Moto boots. The silver detailing on the Moto boots ties in nicely with the silver polka dots of the dress. I try to play up these small details as much as possible.

When I choose an item to wear, I look at its unique features, such as the slits in the first dress outfit, or the silver polka dots in this one. And then I use these unique features to tie an outfit together.

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\\ Outfit details //

• Rebecca Taylor Silk Dress (purchased secondhand via the Real Real spring 2019)
• Vintage leather pants (purchased via Etsy fall 2019)
• Jana Grey Cardigan (old)
• Loeffler Randall Slingbacks (purchased via the Real Real summer 2019)
• Frye Harness Moto boots (Christmas gift 2018)
• Coach grey wristlet (old)
• Botkier grey handbag (won in a charity silent auction fall 2019)

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3. Is mixing color or prints okay, or should I keep it neutral?

When it comes to mixing color or prints, I say do whatever you feel like. There are no rules, even if we have some preconceived notion that certain things aren’t okay (ahem, thanks society for telling us what we should and shouldn’t wear over the years)!

Warm Weather

For this outfit, I kept it pretty neutral on the top with a black tencel/linen button front dress over a pair of leopard print pants on the bottom. I decided to button the dress at the very top of the collar but to only button it down to the waist. This makes more of the pants visible, especially when I walk. I also like that I can still access my pockets.

CHECK out these shoes! I could have added a pair of neutral shoes but I love the pop of color from the orange sandals! I think that this outfit is the perfect balance of professional but with a fun twist. If you have a strict business dress code, this might be pushing it but if your workplace has a more lenient dress code, this type of outfit would be perfect.

Although I’ve experimented with color in the past, it’s really only been over the past few months that I’ve been adding more and more color. These shoes have been one of my favorite purchases. Shoes and accessories can be a fun way to add some color if you have more neutral wardrobe and would like to incorporate color.

Cold Weather

Okay, how is this for some pattern mixing, or matching?!?

My first thought when it came to styling this dress over pants look for colder weather was to add a sweater over top of the dress and to pop the collar out over. But then…I saw this dress hanging in my off season wardrobe and I knew I had to try it, even if it was a total disaster.

So, it looks like it’s a dress over dress over pants kinda situation.

But, you know what, I kinda really love it! You’ll have to let me know in the comments if you’re into it as well or do you think it’s just a bit too much?

I always harp on and on about how important fabric composition is when it comes to wearing multiple items and I don’t see any point in changing now ;).

The leopard print dress that I layered on top is made of silk. The dress underneath is a tencel/linen blend. The tencel gives it a nice silky finish while the linen gives it a little structure. And even though the pants are cotton, the dress are able to move over the pants and each other easily.

I added my brown suede boots to make the look more casual and to make it feel less fussy. I could have added a pair of black boots but they felt like the obvious choice and it felt like there was already enough black in the outfit.

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\\ Outfit details //

• Equipment silk leopard print dress (purchased secondhand via the Real Real summer 2019)
• Tradlands Chelsea shirt dress (gifted fall 2019)
• Old Navy leopard print pants (thrifted locally summer 2019)
• Stine Goya Orange sandal (purchased secondhand summer 2020)
• Free People Suede Boots (thrifted locally spring 2019)

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4. What shoes should I choose?

Ah, shoes. A girl’s best friend, right?!? Infinitely more important that diamonds, wouldn’t you say?

I don’t know about you, but I’ve always had a soft spot for a pair of great shoes! I remember a pair of hot pink stilettos that I owned in college. They made every outfit so much better!

And they’re the one place where you can really experiment with your wardrobe without changing it up too much.

Warm Weather

Lately, I have been really into wearing blue with orange, or blue with tan, or tan with orange. So, why not combine them all in one outfit?

For this outfit, I chose to wear a loose, drop waist cotton dress over a pair of tan equestrian style pants. Most of the details of the pants are hidden but they have the perfect skinny leg to balance the volume of the dress.

I added my orange sandals since they are the perfect colorful compliment to any outfit and my grey handbag. I am also really loving the combination of these orange shoes with this particular grey bag. If you saw my last “Capsule by 5” post then you’ve definitely see this combo before.

Cold Weather

I have been dreaming of wearing this vintage black silk blazer with this particular dress ever since I got the dress earlier in the summer but it’s been too hot!

And I think that the blazer is the perfect length to top a midi length dress.

My black belt bag hasn’t been getting much wear lately so I decided to close the blazer and use the belt bag to hold in place. I love how it added some definition to the outfit, but in a fun, unexpected way.

I also added a pair of leopard print mules as an unexpected addition. What do you think? Would you choose these mules or would you go with a different shoe choice…let me know in the comments!

I also had to try the outfit with the blazer opened to see what it would look like. Honestly, as much as I think the belt bag around the waist is fun, I’m more likely to wear it with the blazer open over the dress.

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\\ Outfit details //

• Mansur Gavriel blue cotton dress (purchased secondhand via the Real Real summer 2020)
• Ralph Lauren Sport tan pants (thrifted locally summer 2020)
• Vintage black silk blazer (purchased secondhand via Etsy fall 2018)
• Stine Goya Orange sandal (purchased secondhand summer 2020)
• Botkier grey handbag (won in a charity silent auction fall 2019)
• Cuyana belt bag (purchased summer 2018)
• Able leopard print mules (purchased fall 2018)

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Which of the above warm weather looks was your favorite? What was your favorite cold weather look?

Is a dress over jeans outfit something that you have tried in the past or would in the future?

Can you think of similar items in your wardrobe that you could use to create similar looks?

To see more ways that I wear these pieces, check out my Instagram account!

Until next time,

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