day to night Sep 27, 2018

Effortless Desk-To-Drinks Style

SHEATH DRESS: c/o Ann Taylor |  BELTED JACKET: c/o Ann Taylor | PUMPS: c/o Ann Taylor LAYERED NECKLACES: c/o Ann Taylor (HERE and HERE) | EARRINGS: c/o Ann Taylor

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.

Professional and versatile can exist in the same sentence—even in the same outfit.  Just make sure to focus on pieces that make you feel good, and that have the ability to adapt seamlessly with just the addition/subtraction of a layer or accessory.  And, maybe start at Ann Taylor.  I bought my first workwear pieces ever there, and they’ve never steered me wrong since.

DRESS: Ann Taylor |  JACKET: Ann Taylor | SHOES: Ann Taylor NECKLACES: Ann Taylor (HERE and HERE) | EARRINGS: Ann Taylor

Thanks to Ann Taylor for partnering on this post!

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12 Responses to Effortless Desk-To-Drinks Style

  1. Joanna says:

    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. Julie says:

    Great look from head to toe. Who makes the black satchel you are carrying?

  3. Merritt Beck says:

    Your pictures are gorgeous Mary! Loving how simple and effortless you make it look!
    xx, Merritt
    The Style Scribe

  4. Kathy says:

    Great look. Presentations like this is why I started following you years ago. You can’t go wrong with Anne Klein.

  5. Beautiful, chic, classy, elegant … I have to use the same words for all your outfits but they are so great!

    Happy Friday xx

  6. ELLE says:

    amazing advice and so helpful, this is such an great look and certainly hits that balance of sophisticated for work but still empowering for a night out after


  7. 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!

  8. Linda says:

    Love this look! Wow! 🌸🍃

    xxx, Linda

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