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)?

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