Winter Workwear // From commute to desk to dinner

winter commuting outfit professional boots for wet weather

Ann Taylor coat xxs petite c/o, ruffle shell xxs c/o, necklace c/o, Halogen cardigan xxs petite, Nordstrom tights S, J.Crew skirt (similar), Sam Edelman rain boots sz 5, Goyard tote

Recently I asked what you guys wanted to see more of, and winter work wear was a popular request! It’s tough to find motivation for cute outfits when you’re just trying to survive the bleak morning commute (and subsequently, the over-heated office building). And it’s easy to give in and just slap on plain black tights each morning. Today’s look is a layered one for transitioning from a slushy winter commute, to a business casual office, and even to post-work drinks!

On The Go – Cold & Damp Commute

This is the reality of sidewalks and intersections right now – salty, dirty, melted snowbanks ready to destroy your favorite shoes. I almost always have commuting shoes and keep pumps in my purse or at an office. These sleek rain booties have been great so far in ran to light snow, but don’t expect any insulation since they are just rubber. I also love this wrap coat (also worn here and here) for layering, since you can adjust the fit to accommodate as few or as many pieces underneath!

petite fashion blog_winter workwear gray coat mustard yellow pencil skirt

At The Office – Winter Business Casual

My experimentation with colored hosiery usually results in Nick dubbing the look as an elf or smurf or oompa loompa outfit. Alas, I’ve pretty much relegated myself to three “safe” shades for professional outfits: basic black (can’t go wrong), dark navy, and charcoal gray. The latter two are nice for more colorful or light-hued outfits, when black might be a little harsh. For example, black looked a little “bumblebee” with this outfit, so I swapped in a softer gray. These control-top tights are nice quality, run small / narrow, and are not too long on my shorter legs. I’ll have to try the fleece-lined version next!

what to wear to work in the winter long cardigan pencil skirt

After Work – Drinks or Dinner

Layering a pretty blouse at the base of your outfit makes it easy to shimmy right into cocktails or dinner. This ruffled top is currently on sale at Ann Taylor (use code FRESHPICKS for 40% off), and is very lightweight and airy with piped sleeves that go all the way around. I also like how it looks tucked into higher-waisted jeans or trousers. The cream color can be on the sheer side, so I wore a nude cami underneath. Here’s a few other pieces on sale at Ann Taylor which I tried on and would recommend:

Georgette ruffled blouse – feminine and nice quality blouse in two pretty pastel hues. The georgette fabric has a good weight to it (weightier than I expected) and is machine washable. Due to the tiny eyelet holes, I would also suggest wearing a skin-toned cami under this one.
Tiered chiffon skirt – I overlooked this skirt a few times online, but it’s actually a great little piece that fits me off the rack better than most AT skirts (due to the elasticized grosgrain ribbon waist). It has rows of pleated navy chiffon with a full lining underneath, and is actually machine washable as well.
Pave scallop dropbezel drop earrings – These are reminiscent of pricier brand earrings and are a nice in-between size (not too small and not overly “statement”). Each pair is super lightweight, and the “dark fuchsia” bezel is actually a pretty medium/deep blue.

colorful winter work outfit for a business casual office
jcrew petite wool pencil skirt for work
What are some of your must-have pieces for winter workwear (i.e. favorite commuting shoes)?

When you purchase through the links on this blog, I may earn a commission. Thank you for your support!

When you purchase through the links on this blog, I may earn a commission. Thank you for your support!

For Daily Posts

Leave a Comment


  1. Anna wrote:

    I was wondering if you got a shaper for the bottom of your Goyard tote like you can get for the Louis Vuitton purses.? Can you send me the link, please?

    Posted 6.20.18 Reply
  2. Amazing way to dress well in this weather!

    Posted 1.29.18 Reply
  3. Pam from Louisville wrote:

    Your pictures could go straight into Vouge Magazine. The camera loves you and you always look relaxed and natural. I am 5.0′ and hate that fashion magazine models are only super tall. Nobody looks like me. Thank you for doing your website. You are my fashion hero. I get great ideas for putting outfits together.

    Posted 1.22.18 Reply
  4. Loving this look, the skirt has a nice color! 🙂

    Posted 1.16.18 Reply
  5. YZ Chan wrote:

    I really like how you styled the outfit for 3 different occasions. And I’ve never thought to wear coloured hosiery, so thanks for the tip!

    Posted 1.16.18 Reply
  6. Maureen wrote:

    Your style is always on point. I like how it is classy but also relatable. Now I just need an office job! Lol 😂 But seriously, love how you mix things up and make it all look so beautiful. Btw, I can’t get enough of your ear muffs. So cute!

    Maureen |

    Posted 1.16.18 Reply
  7. Maggie wrote:

    I love that pop of yellow with the grey! It’s a unique but gorgeous color combination!

    Posted 1.13.18 Reply
  8. Miki wrote:

    How chic. Love the earmuffs and the yellow skirt is such a beautiful sunny pop of color in the cold season!


    Posted 1.13.18 Reply
  9. Amanda Warren wrote:

    I can’t tell from the pictures, but are your heels black or grey?

    Posted 1.13.18 Reply
  10. Janki wrote:

    Thanks for this! I’m headed to another business trip to Denver next week. This helps so much. Quick question, when you have meetings where you’re walking from office to office, do you bring the rain shoes and then change? I find it hard since my male coworkers just wear easy walkable shoes.
    I’m going to buy those grey tights for this trip; they look great.

    Posted 1.12.18 Reply
  11. fatou wrote:

    love the yellow! so pretty

    Posted 1.12.18 Reply
  12. Tiffany Loi wrote:

    Hi Jean! What size is your J Crew skirt? Thanks!

    Posted 1.12.18 Reply
  13. Stephanie mendel wrote:

    By the time you feature the style clothing you can no longer get it from that store

    Posted 1.12.18 Reply
  14. Oh, I like this look! The gray tights really work well with the yellow skirt.

    Posted 1.12.18 Reply
  15. Nina Summers wrote:

    I love your website. This show me how to put pieces together and color. Just excellent!!!!!

    Posted 1.12.18 Reply
  16. Jae wrote:

    Love this look and the ruffles on top! Jean, could you do an updated review on your Goyard tote? I would like to know if it’s still going strong.

    Posted 1.12.18 Reply
  17. Chrissy wrote:

    So cute! I don’t read blogs very odten, but yours caught my attention with the outfit! I like how you link to everything!

    Posted 1.12.18 Reply
  18. Stacia wrote:

    Thanks for your inspiration! If ind it hard to dress in winter. It is cold outside, and warm and dry inside. Changing shoes is a good idea, I will definitely consider that.
    Do you wear something under your top? Isn´t ist to cold?

    Posted 1.12.18 Reply
  19. Gray tights? I never considered that. Since I love colorful shoes I do worry that my black tights don’t look right. I can’t go bare legged in the dead of winter. I am too much of a wimp to expose large amounts of bare skin directly to the cold and I hate getting shoe bites from close toed shoes on my bare feet, so going hose-less is not an option. I would hate for the fashion police to attack me for wearing nude hose. Gray seems like a perfect solution.

    Posted 1.12.18 Reply
  20. Kay Nguyen wrote:

    Your outfit always look amazing! Love the pop of yellow <3

    Posted 1.12.18 Reply
  21. Rachelle wrote:

    This is such a chic work look, love the yellow.


    Posted 1.12.18 Reply
  22. Such a cute look! X

    Posted 1.12.18 Reply
  23. Bless husbands for giving subtle comments when one is experimenting with outfits, right?!? Your smile in the first photo shows me you know you just rock in this outfit. It’s practical, pretty and very versatile. Love, Lieske

    Posted 1.12.18 Reply
  24. I love the outfit! Those colours are gorgeous together!

    I hope you’re having a great Friday!

    Posted 1.12.18 Reply
  25. Thank you so much for sharing these great tips Jean! 🙂 <3 I love this outfit so much, especially the top! The sleeves are gorgeous!

    XO, Elizabeth

    Posted 1.12.18 Reply
  26. This is such a lovely look. Like your use of whites and yellows in the Winter!

    Posted 1.12.18 Reply
  27. Narhee wrote:

    Fantastic look! Love the blouse so much

    Narhee | Made in Mauve

    Posted 1.12.18 Reply
  28. Jean, every time you come out with a new post they become my favourite! I really love your outfits. The colour of the skirt is lovely! 🙂 ❤️

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 1.12.18 Reply
  29. Briana wrote:

    What versatile pieces! This outfit is so classic and definitely works for both occasions!


    Posted 1.12.18 Reply
  30. La Bijoux Bella | by mia wrote:

    Always a beautiful look! 💗👍🏼💗


    Posted 1.11.18 Reply

Get the newsletter!

What updates would you like?