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3 Ways to Wear Black Pull-On Pants

Over the last year, I’ve been asked to share more outfit inspiration modeled on a “real person” instead of our flat lays.

And while I would love to share a range of different body types, that’s currently not in the cards.

I would either have to ask my friends to model, and I love them all too much to open them up to being body shamed online, or hire professionals, and there is no budget for that.

So, the best I can do is wear the clothes myself.

I recently heard a quote that resonated with me, “Everything you want is on the other side of feeling embarrassed.

No words have ever been more accurate. Basically, everything I do to run and grow this business is mortifying.

When I first started, I had zero intention of being front-facing, but obviously, the landscape changed very quickly, and the unfortunate reality is if you want to scale and have reached, you have to put yourself out there.


Here’s how this works. 

There’s still a place for flat lays in our content, they have a lot of value, but we are starting to incorporate more photography.

The challenge is that items sell out fast, and promotions come and go, so our articles must be published quickly. 

Take today’s feature, for example.

We highlighted these pants in our Sunday Sales, they show up as a best seller by Tuesday, and today we can share three real-life outfits using other recently featured pieces.

I pay for all of these clothes with my own money. On the rare occasion, an item is gifted, it will be clearly noted. 

As always, there is no photoshop and no retouching of any kind.

So let’s kick this new adventure off with the Jamie Elastic Waist Pant from J.Crew Factory. Priced at $52.50, in sizes classic, petite, and tall in 00 – 24 in black and navy. 

The current promotion at J.Crew Factory is an additional 20% off any order of $125 or more.

3 Ways to Wear Black Pull-On Pants

I am 5’10 and am wearing a size 10 Tall.

The length is perfect for me; as you’ll see, it works with shoes of different heights.

If you are in between sizes, go up one. I could get away with the eight, but this fits better in my mid-section in the 10.

I am so impressed with the fit and quality.

They are versatile pants you can dress up or down in a fabric ideal for transitional seasons and spring.

For our first outfit, I went casual with other well-priced items that will look familiar.

With Sneakers

For this look I used the J.Crew Factory Girlfriend Tee Shirt.

Ladies, this is an awesome, inexpensive, classic white tee that isn’t transparent.

Available in XXS – 3X, one for $20 or 2 for $35.

Tons of colors available. I took that large which is a little big but I think it will shrink.

Then I threw on this Old Navy Denim Jacket, it’s their Distressed Classic Jean Jacket, and it’s under $50.

Available in regular, tall and petite in XS – 4X. I’m wearing a regular tall.

My 13 year old has a sick sneaker collection, so I helped myself to her Adidas Superstars. The black detail is shiny, like a patent leather and there is gold detail that’s hard to see in the picture.

They are pretty well priced at $100.

I grabbed this popular Amazon crossbody bag, available for $55. The black ALWAYS sells out, but the brown option is currently available.

And because the look is casual, I added this faux tennis necklace for contrast, layered an initial necklace and added these hoops, also from Amazon, in the 20 MM size.

With Loafers

For this look, I pulled out the Sam Edelman Loraine Loafers.

These are just a good, classic, comfortable loafer that pair great with basic bottoms.

Sizes run true.

I threw on the J.Crew Factory Teddy Sweater in this sophisticated tan and black stripe.

Available in XXS – 3X, in a range of colors and patterns, sizes run a little small, so go up one if you’d like some room.

I’m wearing the large, and I like how it fits, but I’m going to lay it flat to dry so it doesn’t shrink.

And the only accessory, aside from my every day rings and bracelets are these pearl drop earrings from Amazon that I am mildly obsessed with.

With Pumps

Finally, I’m wearing the Marc Fisher Block Heel pumps in black suede that I’ve been featuring like crazy.

I love the look, the block heel is comfortable and they are both modern and timeless and they work with pants or skirts.

Available in a range of colors, some on sale, the black suede is regular price at $160.

The blouse, I featured in yesterday’s Outfit Formula.

I’m wearing the light blue, in large, available in S- XXL for $30.

Note, it’s not pulling across my chest, it’s just bunched under my bag. I promised photography, but nothing professional. lol.

I kept the same Amazon Pearl Drop Earrings, and grabbed my favorite new bag from Coach. The one I have is sold out but it’s similar in price and style to this one.


Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


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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Kathleen bove

Wednesday 1st of November 2023

I have been trying to rejoin the private Well Dressed Life on FB. I changed cell phone and my FB account did not crossover. Would you please accept my request to rejoin under Katheen Johnson Bove. I miss following on FB and exchanging private conversations with other women. Kind Regards Kathleen Johnson Bove

Megan Kristel

Wednesday 1st of November 2023

We don't have any requests under that name.


Monday 6th of March 2023

Great choices for real women. Thanks for the inspiration! You look great


Saturday 4th of March 2023

Thank you for these photos! I love seeing the clothes on a real person! The flat presentation is good for what to wear together, but this helps me see how to wear it.


Friday 3rd of March 2023

Have you ever tried the brand JAG in pull on pants?

Jeannie Jonassen

Friday 3rd of March 2023

Love your hair!!!


Friday 3rd of March 2023

I have a question about pull-on pants: it’s ok to tuck in your shirt w them (you look great, but worried I would look like I’m wearing maternity pants)? Also, if you tuck in your shirt, do you need to wear a belt? And is it ok to wear a belt if your pants don’t have belt loops? Sorry! Obviously the pull-on pants are stumping me. I have them and wear them all the time, but always w my shirt out. Thank you!


Friday 3rd of March 2023

These pants are awesome and I suggest them to people all the time. For those that can make the trip in a J Crew Factory, let me tempt you with more deals. Megan is correct on the promotional pricing. Here are additional J Crew Factory in store only options: like online these pants at 40%. If you are a J Crew credit card holder you will receive an additional 20% (all month) and if you purchase 3+ items another 20%. There are also in store discounts given to educators, medical personnel, first responders and military. In-store you are allowed to stack two discounts in addition to the store promotion. So for example, 40% off 20% for the credit card +20% for 3+items, or 20% for 3+ items and 15% for being a nurse.


Friday 3rd of March 2023

Thank you for all the thought, time and energy you put into your posts. I actually like the flat layouts where you show outfits. But it is nice seeing them on a real person once in a while and you are a beautiful model. I always learn something from your lovely blog.

Rebecca Davis

Friday 3rd of March 2023

Your modeling is so true to life not POSEY!! How about featuring Chico's?


Friday 3rd of March 2023

Thanks for putting yourself out there and sharing your outfits. Your content is fantastic and I can’t tell you how many of your recommendations I’ve purchased over the years. Job well done!


Friday 3rd of March 2023

Thank you for the great content! I admire your courage in putting yourself out there. You look terrific. I LOVE the J. Crew Factory Girlfriend Tee! It’s the ONLY white tee I have ever bought that I like. I went back and bought another white one, plus navy and gray. If you’re busty, it’s a great fit! Now I’m going to check out these pants. :)


Friday 3rd of March 2023

Thank you for putting together all that you do every week! To see you wearing the outfits is a big bonus and much appreciated. You look fantastic!

Linda LM

Friday 3rd of March 2023

You look great! I admire the courage of people who put themselves out there, because even if they look as amazing and healthy as you do, people are so nasty. I feel sorry for bloggers who go into public dressing rooms and then have to apologize for such stupid things as smudges on someone else’s mirror, or the color of their lipstick. I’m much shorter than you at 5’5”, but it’s still helpful to see where things land on your waist and ankles. And I love to see a put together outfit, complete with bag and accessories. You are a true professional, and it shows.


Friday 3rd of March 2023

You look fabulous! Beautiful! I understand it’s hard to put yourself out there but don’t doubt yourself, you are amazing. Thanks for all you do. I’m a new subscriber and your newsletters are such a fun part of my day!


Friday 3rd of March 2023

I love the look of these pants on you, but I have large calves for my size (I'm a size 6 but my calves are around 16.5") so straight slacks sometimes don't work as they bunch up below my knees everytime I sit down. Would you mind measuring the width of these pants around the calf area and sharing that on your blog? I'm not on facebook or I would ask there.