Effortless Desk-To-Drinks Style

Workwear pieces that understand you have a job to do—and dinner plans afterward.

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Square Neck Ponte Sheath Dress


Checked Belted Jacket


Frannie Suede Bow Pumps


Textured Chain Link Necklace


Pearlized Double Layer Necklace


Pearlized Drop Earrings

Somewhere along the line, professional clothing got a bad rep. I think it has something to do with cheap grey pant suits and ill-pleated trousers, I don’t know.  That remove-hair-clip-shake-head move at the end of the day suggests that we’ve spent the entire workday in discomfort, and I’m not into it.

The idea that workwear can’t have fun is a tired one.  It’s also doing the classic #officestyle aesthetic a disservice, and you know my love for this particular genre.  I’m here to tell you that it is possible to love living in your workwear so much that you’ll even take it out for drinks.  I’m willing to prove it, with this head-to-toe Ann Taylor look that illustrates the point.  And is also way comfy, FYI.




Stylish and versatile, Ann Taylor’s approach to workwear understands that you have a job to do—and dinner plans afterward.  It’s almost too easy to adjust the brand’s classic pieces into something polished and pinot noir-ready in an instant.  Think simple, polished layers and accessories that go with essentially everything.  Honestly, can you remove a blazer?  If you can, you can master day-to-night.



In this look, I’ve opted for a square-neck ponte sheath dress (seriously feeling the square neck this season) topped with a checked belted jacket that’s a whole thinkpiece in versatility on its own.  I’m seeing it over jeans for brunch, but do you.  Add to that a bow-toe suede pump (I’ll take one in each color, thanks) and a couple classic pieces of pearl accent jewelry, and you’re polished enough for work but not so professional that your friends feel like you’re selling them life insurance at cocktails.  Fun fact, Ann Taylor offers petite, regular, and tall sizing (I’m wearing tall) so add that to the list of reasons to love.


12 thoughts on “Effortless Desk-To-Drinks Style”

  1. It’s a great workwear outfit. Very professional but not staid. I’m 5’8” and wondering how tall you are so I know where the dress will hit?

  2. Now this outfit is spot on, and it kind of reminds me of a look from the 80’s .. and I mean that in all the best way! I was looking at a Vogue magazine from the 80’s back in July and your outfit very much reminds me of what I saw. I too used to be so against work clothing because I thought it consisted solely of over-sized blazers and as you said, pleated and creased trousers. However, with some more fitted pieces with a few fun colours put into the mix, you’ve got yourself a fabulous outfit!


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