Going Casual in a Chanel-Inspired Little Black Dress

“Luxury must be comfortable,
otherwise it is not luxury.”
~ Coco Chanel

Coco Chanel was one of the first designers to bring sportswear into everyday wear. She saw the necessity (and luxury) in comfort. One of the many values of making comfort a priority was the freedom it gave women to move like normal people. If a person is weighted down in heavy undergarments, cinched to the point of fainting, and can’t walk briskly due to lagging hemlines, it makes it nearly impossible for that person to function in any role other than standing and looking pretty.

Womein in 1910 fashions.
Women of the 1910s changed a lot throughout the day, wearing a different dress for different occasions. These gowns were for afternoon outings.

By making sportswear fashionable, women became free to move and breathe and think. Jobs women took during World War I became easier to do in looser fitting outfits. Housework, childcare, and cooking also became easier in clothes that moved with the wearer.

Women from the 1920s wearing fashions of that era.

Did Chanel’s Ideal for Luxurious Comfort Mean Yoga Pants?

So, here we are now, nearly 100 years later, wearing yoga pants to do everything in. I’m not sure that’s what Chanel had in mind when she started this fashion revolution. Yet, our lives today don’t allow for a myriad of changes throughout the day. Life isn’t as segmented as it was when Chanel brought her sense of comfort to fashion. We need outfits that can take us from a meeting with clients to lunch with friends to a walk with the dog without feeling overdressed or giving up style.

In my last post, I demonstrated how a simple change in cardigan and belt created different looks for a Chanel-inspired Little Black Dress. My focus for that post was on slightly dressier occasions, like work or date night. The next logical step, for my life at least, was to test whether this same LBD was versatile enough to handle my most casual outings. I wanted to know if a Superman-like quick-change was possible — to go from work clothes to play clothes without having to completely start from scratch.

Coco Chanel's original Little Black Dress next to a modern, casual version.
Coco Chanel’s original LBD was actually two separate pieces, so I did the same with my version to make it even more versatile!

Below are three looks I put together using the same top and skirt from my last post as a base. I hiked up the skirt to my natural waist, changed out the shoes, added leggings, and switched out jackets and belts to create the different looks. This all took just a few minutes.

Three different casual outfits using Coco Chanel's original idea for the Little Black Dress as a base.
For these outfits, I pulled the skirt portion up to my natural waistline. It shortened the skirt, thus giving it a more casual look.

The Verdict

I’d say the versatility of Chanel’s Little Black Dress holds up well in today’s world, especially if you stick to her original version of a separate skirt and top. Separates allow for even more flexibility. For instance, my skirt has an elastic waistband, which I pulled up to my natural waist for the casual looks and tugged down to lengthen the look for the dressier styles. The options, then, are seemingly endless when mixed with different shoes, layers, and accessories. The ultimate result is that I never feel overdressed or underdressed wearing these looks in today’s world and I’m not relegated to yoga pants as my only casual option. I simply feel put-together and stylish.

Shop These Looks:


Eileen Fisher Long Sleeve Silk Tee  |  Eileen Fisher Pleated Jersey SkirtSimilar at ThredUPFind similar on eBay  |  Eileen Fisher Leggings

Look 1:

Theory Denim Jacket: Similar on ThredUP Here (XSP), Here (MP); Similar at Talbots  |  Eileen Fisher Scarf: Similar Here and Here |  Cole Haan Zero Grand Oxfords

Look 2:

Cashmere Eileen Fisher Cardigan: Similar Here, Here, and Here  |  Eileen Fisher Obi Belt: Similar Here, Here, and Here  |  Eileen Fisher Soul Booties (On sale!)

Look 3:

Eddie Bauer Microtherm Stormdown Jacket in Salsa  |  Cole Haan Zero Grand Oxfords

Affiliate link disclaimer: Please note, with the exception of the Eddie Bauer coat in this post, all the item links above are affiliated with companies I am associated with. By clicking the links and purchasing from those stores, I might receive a small commission. I do not put these links lightly — any company I represent is a company I buy from regularly, including eBay and ThredUP. By purchasing from these stores, you support the work I do here and I greatly appreciate your support! 


Leave a Comment

Your email address will not be published. Required fields are marked *

  • You have a great eye for detail Sherry and I am impressed with the number of looks you have created out of these base layers. I would never have thought of all these different combinations and would have got stuck at heels and a cardigan! Really enjoying your blog. 🙂

    • Thank you, Astrid! I’m so glad you’re enjoying it! If it wasn’t for Chanel and old photos, I would get stuck too! I get distracted by almost anything beautiful and I want to try everything. The photos help tune my focus. I really appreciate your feedback!!

    • Thank you, Jodie! I’m so glad you like the outfits. The thing I like most about them is that they are comfortable and I don’t feel under- or overdressed. I may have to keep going on this theme — see if I could REALLY dress up this base outfit for something like a night at the symphony. What do you think?

  • I frequently wear leggings beneath a shorter, sporty skirt. I find that it makes me feel much more comfortable when my crotch area is covered in public and I can run around looking completely appropriate. Most of the short skirts just aren’t appropriate for a 65 year old woman… There’s just no denying the comfort of leggings but I want to feel properly covered too.