Reader Request: Dressing Down Fancy Work Duds – UPDATED

Reader Kim said:

I’m not sure if you’ve done this before, but I’m always trying to figure out ways to dress down some of my dressier items for work. I’d love to see your take on that.

Originally, I tried to tackle this post here, but thanks to a few astute reader comments, realized that I’d missed the mark! Kim doesn’t want to know how to mix dressy and casual, she wants to know how to take make her fancy work clothes work outside of work. (Say THAT five times fast.) So let’s give that a whirl.


Obviously, this won’t work with most sheath dresses. But above-the-knee frocks with a bit of a flare in the hem generally look DARLING paired with cropped leggings and flats. Wrap dresses, like the one shown above, are absolutely ideal for this formula. Flip through your workweek dresses and see which ones will look adorably dressed-down worn with leggings.


I’ve definitely worn my printed tights to the office, but they are just a bit more casual than my solids. When you pair funky tights with a conservative dress or skirt, you’re adding sass and whimsy to the overall mix. I consider that a fabulous way to dress down your work wear!


Military jackets and blazers, denim jackets, leather coats, and anything that’s been distressed will instantly tone down the dressiness of skirts, slacks, dresses, and heels. Try your black suiting pencil skirt with a graphic tee and military blazer. Throw a jean jacket over that sleek sheath dress. You could even do a bomber with a button-down and jeans. Rugged jackets work beautifully with sophisticated, work-appropriate pieces.

I still maintain that wearing jeans with virtually any work-appropriate top or blazer will make for a stellar ensemble, but I suppose that’s common knowledge at this point.

How do you dress down your fancy work duds? Any other tips to share?

UPDATE: After a few curious comments from you folks, I did what I clearly should’ve done to begin with: I wrote to Kim for clarification! See her comment here, and it sounds like between today’s post and the previous I’ve covered her original question. However! For those looking for tips on making truly dressy items – like cocktail dresses and similar – work for the office or everyday life, here are posts that cover that ground:

Hope that helps!

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  • I do these things – most often I switch out a work blazer for a jean jacket, and change into flats, sandals or flat boots. I take off dressy earrings and/or necklaces. Then I add more lipstick, and go out for a glass of wine at the best Irish pub in town. : >

  • I definitely agree with the jean jacket and different jewelry ideas! I wear a suit most days. I also find that changing from polished shoes to funky oraa trendy ones helps, much like the tights idea. Also you can wear your dressier tops that usually go with suits with jeans or with more casual skirts. I would never have the guts to wear a black pencil skirt outside of work, church, or a cocktail party tho!

  • Most of the time, I don’t really bother to try dressing down fancier work clothes. Maybe it’s because my work environment is so casual or because my off-hours activities are more likely to require dancewear. Much more often it seems like I’m figuring out a way to sneak a cheap Old Navy t-shirt into my business-casualwear instead of a blouse.

  • Melissa

    Black tights or full length leggings tucked into boots, dress down almost any dress or skirt(including sheaths). I don’t like the cropped leggings with dresses, it looks awkward on anyone over 10.
    Jeans or cargo pants dress down any top or blazer.
    I also find wedges dress down dresses as well.

    • Barbra

      Agreed about the cropped leggings- totally awkward…

  • Anna D.

    Okay, is it only me who read this question as dressing down fancy items – like evening wear – to make them work suitable? Though I can see it the other way, too. It seems to be the most ambiguous question possible! (Is it dressing down dressier-items-for-work, or is it dressing down dressier items, for work?)

    • Sal

      Maybe! Margot had the same thought.

      I look at the question and see “dress down my dressy work items.” I need to hit Kim up for clarification!

  • Margot

    “dress down some of my dressier items for work”

    sounds to me like she’s asking for advice on how to wear a cocktail dress to work, not how to wear work clothes outside of the office no?

    • Sal

      Bah, could be! I clearly am never going to get this question right …

  • Since my work wardrobe consists of a lot of button-up blouses, to make them more casual I layer a colorful cami underneath and undo a couple of the top buttons.

  • Sal

    Just e-mailed Kim for clarification. I feel like I’m chasing my tail …

  • Anne

    I think Chuck Taylors add a casual charm to just about anything. (you could do wellies in the wet season) I also like to mix in super casual accessories like ammo bags, studded belts and cuffs, heavily webbed and grommeted belts. I have seen down jackets and vests added to dressier outfits. I’ve always pined for one of those photo-journalist’s vest. I think it would look great with anything. I think both the Brits and the French do the dressed down thing really well. If I didn’t dress down my nicer items, I wouldn’t have much call to wear them.

  • Dee

    Hi, I am with Margot and Anna D on this one, I read it that she wants to know how to possibly dress down some of her fancy outifts (that maybe she has only worn once to a wedding, or similar) so she can get more wear out of them. We would all love to know the answer to that one! I think that would be very hard to do except maybe in the case of separates. Dress down a velvet skirt, yes, dress down a chiffon strapless gown — I don’t think so! I guess it depends on where you work and what kind of pieces of clothing you have. And of course your creativity — What do you say Sal??

  • Kim

    Hi…yep, this was my question. I think you have hit it here Sally. My question was about how to dress down say a dressier dress that you could wear to the company Christmas party but then change up to wear to work. I had two dresses that could be casual cocktail and really loved them and didn’t want them languising in my closet.

    Dress #1
    Dress #2

    For the first one, I ended up wear tall black boots and putting on a cashmere sweater over it.

    The second one I’ve worn a gray 3/4 sleeve sweater over it so the sleeves still hang out. It looks cute. And I’ve worn an assymetrical drape cardigan over it. I’ve worn riding boots and other fun shoes with it.

    I realize these aren’t dressy cocktail party dresses but for me and I’m assuming lots of others, they are too dressy for normal work as is.

    Thanks Sally! I think you hit the mark with your post!


  • Now, the cocktail dresses or party dresses to work business, that I am on top of to a certain extent (although I have one red and purple silk Boden dress that I have not managed to get up the nerve to wear for dailywear). I have a lot of soft silk print dressy-dresses, that are definitely not everyone’s idea of businessladywear. My absolute favorite item for taking a little bit of the shine off of a fancy piece but still letting it show at work are my streamlined-but-drapey cardigans from Kische. I got them at Nordstrom last year. The pintucks give them enough shape not to look like you’re wearing a bag, but they are relaxed and easy. They show some of the dress, but not your shoulders. I know Nordstrom has them in stores this year because I saw cream and navy ones when I went in there during sale.

  • Eliza

    A few more ideas for dressing down clothes. 1. Go with a casual hairstyle. I like wearing my hair up, but sleek styles end up looking very formal with my structured clothing. Flattering flyaways look a little more casual.
    2) Layer shirts. The trouble with jackets is that if you get hot and take them off, you’re back to looking formal. I’ve been tying silk blouses (the semi-shear, matte kind) over some of my stuffiest dresses, and it works pretty well.The fabric is nice like the dress, but the styling of the shirt makes everything looks much more casual. T shirts under or over dresses can work as well, but they tend to look wrong if the good piece is made of dressy fabric.
    3)Keep handbags on the casual side. I can use the same clothes for college classes or formal dinner with my grandparents just by swapping tights, flats, and my beat up leather messsanger bag for stockings, heels and a structured vintage bag.

  • Tara

    I love your outfit above with the blue dress, multicolored tights and brown boots. I also adore your hair in that pic – it makes me jealous of your curls!

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