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Three Cute Outfits with Black Jeans

We receive so many requests for posts featuring cute outfits with black jeans so today I’m sharing a few that are practical, chic, and can be created with pieces you may already have in your closet.

Black jeans are an obvious wardrobe staple that you can dress up or down.

Below, I list my top picks for black jeans at all price points, share tips on how to best care for them and offer inspiration on how to style them for a day of working from home, a casual weekend, and a date night. 

And please keep in mind, because our readership is far reaching, everyone is experiencing various forms of restrictions differently. My priority here is first to help give practical tips, and also keep things forward thinking and optimistic 🙂 

Let’s start with black jean options: 

Black Jeans: High, Mid, and Low Range

Black Jeans

High: Paige ($179) , Mid Range: KUT From The Kloth ($94), Low: Old Navy ($20). 

Premium denim is expensive for a reason. Long time readers know my focus is always on buying the best you can afford, with the understanding that just because something is the most expensive doesn’t mean it’s the best. 

Brands like Paige (above), AG, Citizens, etc., all focus on quality material and fit, and they last much longer. 

Unfortunately, they don’t offer much in inclusive sizing. 

In the just under $100, or “mid” range, I like KUT from the Kloth. The Diana (above) has a curvy cut and is available in missy, plus, and petite. Consider sizing down in these. When you try them on for the first time, they should feel tight. Tight like you are going to want to get the next size up. 

Don’t, because they stretch out immediately. 

Finally, we love Old Navy around here. They have a completely inclusive size scale (including tall) and are decent quality for the price. These are $20 jeans, so don’t expect them to last longer than a season or two. They will shrink and fade faster than the better brands. 

Related: The Best Jeans for Every Size at Every Price 

Care of Black Jeans

So you get the most out of your purchase, it’s important to care for them properly. Do everything you can to avoid washing them. Of course, if you stain or spill something on them, you have to wash them. But if you’ve only worn them for a few hours, fold or hand them back up neatly until your next wear. 

I know that sounds gross, but once you start to wash them, they will shrink, fade, and generally lose their shape. This goes for all jeans.

It’s helpful to have more than one pair so you can rotate wear. Spot clean when necessary, and when you are ready to wash them, turn them inside out and follow the instructions on the tag. 

Okay, let’s get into outfits … 

Today I created three cute outfits with black jeans, a laid back look, a casual chic outfit, and something simple for weekend date night. 

Three Cute Outfits with Black Jeans

Three Cute Outfits with Black Jeans

 Outfit One: Cardigan, $80  |  Sneaker, $110  |  Tee, $25  |  Bag, $75  |  Outfit Two: Top, $38   |  Vest, $180  |   Booties, on sale $50 |  Bag, $80  |  Outfit Three:  Wrap Top, $30  |  Pump, $118 black  |  Bag, $55 


Work from Home Outfit


Three Cute Outfits with Black Jeans

For our first look, I was thinking of days working from home, or travel, when you have to head to the airport or train station (eventually). I’m using a skinny black jean, you could also wear a slim straight leg.

Grab a basic white tee; I like these v necks at J.Crew. Then, add a long cozy layer. I’m a big fan of H&M.  This cardigan is a wool blend, and I love the color – it looks extra sophisticated. 

To keep things interesting, we used a leopard printed slip-on sneaker by Keds x Kate Spade. 

I included this Sole Society weekender to round out the look for travel. 

Chic Weekend Outfit


Three Cute Outfits with Black Jeans

I wanted to find a Breton top with a long sleeve in black and white. Happily, Boden makes the perfect one for around $40. 

Layers that add interest without bulk are essential to incorporate as the weather cools. So, I went as classic as it gets with a Barbour olive vest. (In my mind, I spend weekends in the English countryside.) 

Add a pair of ankle boots, like our go-to Sam Edelmans in putty, and a crossbody bag (above in champagne), and you’re set for the day. 

Date Night Outfit 

Three Cute Outfits with Black Jeans

Keeping things simple is the key to getting dressed and out of the house on the occasional date or girl’s night out. 

Last year, a friend was wearing a beautiful blouse at a friend’s 40th birthday dinner. When I asked her where she found it, I nearly fell off my seat when she said Express. I know! She said, but some of their things are great and affordable. 

And isn’t that just what we need a night out tops to be? Because I have no room in my budget for a $200 top.

This pleated detailed wrap blouse is gorgeous. It’s fun, a little sassy and about $50. Try on a few sizes as they run small. 

Add your black pumps, like these popular 12-hour heels from Banana Republic, or a heel with an open toe when the weather warms up a little more. Finally, this quilted black envelope clutch is $55 and adds just the right amount of texture and interest to such a simple look. 

Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist View Post and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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Three Cute Outfits with Black Jeans

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Tracy Gray

Friday 30th of September 2022

Love all three suggestions! I like black jeans for variety and these ideas are perfect.

Angela P

Thursday 26th of November 2020

I purchased a pair of Kurvy Kut from the Kloth skinny black jeans and can't believe how well they fit! So happy with my purchase and the fit that I think I'll shop for some additional jeans


Friday 25th of September 2020

Another great article and I will be using all the looks mentioned. I love your articles and it has really helped me revamp my wardrobe

Amy Cornwell

Thursday 24th of September 2020

I have keep my dark blue wash and black jeans in the freezer! Keeps then fresh and no worries about shrinkage.

Sharon J McGee

Thursday 24th of September 2020

Last year, I bought a straight pair black jeans (NYDJ) and a skinny pair (Madewell) and both had a horrible smell to them even after washing. Is this typical?


Thursday 24th of September 2020

Great post! I just bought some Madewell black jeans that are supposed to stay color-true over time. We’ll see! I also avoid washing jeans as much as possible.

I mentally spend weekends in the English countryside, too! 😉 I have been glued to the Joules website lately, also Marks & Spencer.


Thursday 24th of September 2020

I have found that washing my jeans inside out, in cold water and using Woolite for Darks keeps them true to their color a lot longer. In fact, I use it for all my colored clothes.

Ruth Lanwarne

Wednesday 12th of January 2022

@Alicia, This is exactly what I do too and keeps the colour from fading as much. I also use a short wash as just really want to get them back in shape and freshen them.


Thursday 24th of September 2020

I totally agree with you. I love Woolite for Darks !!!!!!!!! Makes your clothes look so much nicer and last a very long time . I rinse my new jeans in vinegar to set the dye. If not you will have dye all over when you wear them .


Thursday 24th of September 2020

I love this post! That blouse from Express is awesome-looking. I hardly ever shop at Express. I checked out their website, and am thinking of ordering it in Black (the white is sold out). I'm not sure what size to order online - as you said that it runs small, but many in the Comments section says it runs large (or TTS). I'm usually a Med in a top from JCrew or BR (36D, 5-7",165#). Do you have this top, and if so, what size would you recommend?


Thursday 24th of September 2020

I shop at Express, Banana, and JCrew regularly, I’ve found that Express sizes are similar to the other two.

Rebecca E

Thursday 24th of September 2020

Love this! I will give you a heads up that the Boden stripped top is on super back order! I purchased one at the end of August and I was informed that it won’t ship until November.


Wednesday 19th of February 2020

Love the post and the ideas. Thanks for including three price points on the jeans!!!


Tuesday 18th of February 2020

Megan, I love the three outfits you posted. I can totally see myself in each one. I do have a question for you though. I have recently re-entered the working world again and am looking for a GOOD dress pant that I can wear to the office. I’d like to find a pant that comes in different colors, black for sure, a darker gray, navy, etc. do you recommend and particular brand?

Megan Kristel

Tuesday 18th of February 2020

Thanks Kim! A couple brands come to mind, Lafayette 148 makes beautiful suiting separates. They are expensive, but are a wonderful quality and come in all the basic colors. They do go on sale, these are at OFF Fifth right now.

Of course, everything depends on your shape, but I would also look at J.Crew, Ann Taylor, Talbots or Banana Republic since they have the best range of sizes.

Suzanne Clarkson Umile

Tuesday 18th of February 2020

Hi Megan! Another excellent post! To your point about not washing jeans (or doing so very infrequently)....I have seen this before and at first, reacted as most of us would. But I decided to steam my jeans about every 2-3 wearings. It makes them look fresher, and steam is pretty darn hot! Most likely hotter than the water we’d use in a washing machine. I got the idea for jeans after reading about steaming the insoles of sneakers to kill bacteria/odors. You may want to give this a try.

Tammy Durnford

Saturday 16th of March 2019

Great recommendations! I can see myself wearing these outfits. I’m going shopping!


Megan Kristel

Tuesday 19th of March 2019

Thanks Tammy!

Tracy Gray

Friday 15th of March 2019

I love all three of these ideas. I do have a great pair of black jeans that l love and now I have some options for different occasions that may come up.

Megan Kristel

Tuesday 19th of March 2019


Mena Roby

Friday 15th of March 2019

Especially love the date night look! And thanks for including links for your recommendations. The Kate Spade sneakers are adorable. I look forward to your daily posts!

Megan Kristel

Tuesday 19th of March 2019

Thanks so much Mena - those Kate Spade sneakers are really sweet!