Office Outfits: 5 Ways To Style Vince’s Pleated Midi Dress (Fall/Winter)

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I’ve been meaning to do a workwear edit featuring a dress, but my usual technique of collages/paper dolls doesn’t work nearly as well with dresses. The proportions, especially when layering, can be really tricky. Unless one is opting for Put On Dress, Add Sad Cardigan (which, hey, we’ve all been there), in order to come up with layered office looks that actually work, I’ve gotta put the things on my body.

The question, however, was: with what dress?

I wanted a dress that could be worn to work on its own (this will be debatable), but could also work under a bunch of different types of layers. So big, interesting sleeves were out. I was also hoping for something fairly year-round-ish. And since this dress is already going to skew somewhat conservative (again, work) I keep hearing Linzi’s voice in my head yattering on about “appropriate” dresses that she uses for boring school functions and whatnot. So maybe a dress that is pretty or interesting enough to also be worn outside the office.

Enter, Vince’s Pleated Midi Dress (part of the NSale, no less).

I saw promise of office outfits in this Vince midi dress because pleats almost always look better IRL

dress (s) | heels

I was eyeing up this dress primarily because most of my favorite pieces in this year’s NSale were all Vince. This is noteworthy because, at first glance, the Vince products in this year’s NSale seemed boring and borderline awful. It wasn’t until I put a few of them on that I realized there are some serious gems hidden amongst the sea of sad. (Someone needs to have a conversation with Vince or maybe Nordstrom about the styling). Anyway, I saw promise in the pleats because pleats almost always look better IRL. And I was interested in the styling possibilities of the drawstring waist: Cinched in? Drop waist? Hmmm.

5 Business Casual Ways to Style Vince’s Pleated Midi Dress For Fall

Turns out this dress is freaking great. Despite the conservative, office-appropriate proportions the skirt is wildly feminine and a little flirty. And the whole dress is really fun to wear. Knowing that pleats don’t photograph nearly as well, I threw together a little reel of all of these outfits, so you can see how they look IRL.

Below are six ways to layer this dress for work.

1. With A Cropped Blazer

This is my standard office fall edit for basically any work-appropriate dress: tall boots, cropped blazer. Love it.

dress (s) | blazer | boots (similar)

This would be my standard office fall edit for basically any midi dress I want to turn into work clothes: tall boots, cropped blazer. Love it.

NOTE: While I originally tried on (and love) FRAME’s cropped NSale blazer, the black blazer I’m wearing here is by Free People. It’s great, and a fraction of the cost of FRAME’s.


2. With A Sweater Vest

To make this work outfit more interesting for fall, I would also throw a trendy sweater vest on over the pleated midi dress.

dress (s) | sweater vest | boots (similar)

To make work clothes more interesting this fall, I would also throw a trendy sweater vest on over a dress. And OH MY GOD my exact vest is on sale at Saks OFF!!

If bare arms are a work no-no for you, the whole thing still looks cute under that cropped blazer, too.

If bare arms are a work no-no, the whole work outfit still looks cute under that cropped blazer, too.

dress (s) | blazer | sweater vest | boots (similar)


3. Over A Button-Up

Un-cinching the wait for a baggier fit is a little edgy + it makes it easy to layer this dress over button-up shirts and/or turtlenecks for an air-conditioned office.

dress (s) | top | boots (similar)

Ok, this is exciting: Because of that cinched waist, you can un-cinch it a little and get a vibe that’s alllllmost romper-like. Or playsuit-like. It’s cool, a little edgy, and means that you can layer this dress over button-up shirts and/or turtlenecks. It all works.


4. Under A Cropped Sweater

Throwing sweaters over a dress to make it a work outfit isn't exactly novel, but it's still cozy, cute & something I will wear the heck out of this fall.

dress (s) | sweater (similar) | boots (similar)

Ok, this is less exciting — throwing sweaters over a dress isn’t exactly novel. But it’s still cozy, cute, and something I would wear the heck out of.

The key here is to look for a sweater that’s more in the cropped family. This striped one from Free People might work well, it’s more cropped than the sweaters I’m wearing.

And I appreciate that this wine color can be paired with all sorts of gorgeous fall tones, even earthy or army-ish greens:

The wine color of this Vince midi dress can be paired with all sorts of gorgeous fall tones.

dress (s) | sweater | boots (similar)


5. Under A Sweater Dress

I'm wearing a short sweater dress as a top layer, but you could go even longer, letting the pretty pleats peek out wherever they may.

dress (s) | sweater dress (similar) | boots (similar)

On the opposite end of the spectrum….go long with the sweater. Like, really long… I’m talking dress length. Here I’m wearing a short sweater dress, but you could go even longer, letting the pretty pleats peek out wherever they may.


xo,

S

3 COMMENTS

  1. Somehow those pleats really conjure the church lady wear of my 80’s childhood–but the color and length . . . yes! Now off to find my own version.

    I’d love to see a few other similar boot options, and maybe even more pressing, boot options for multiple scenarios (jeans and professorial office wear) now that wide-leg pants are the thing. I’m sure you folks have wisdom on that front, and I’m officially stumped!

  2. Dang it, just when I thought I was done shopping the NSale! This dress is definitely appropriate for work and “boring school functions”…lol. I love all the different ways you styled it. This belongs in my closet!

    I just wanted to say how much I appreciate all the work that goes into covering the sale (and in general). The info you provide is so helpful and makes it easier to navigate the sale. If Linzi hadn’t done that Frank & Eileen post a while back, I wouldn’t have been inclined to try the pieces included in this year’s sale. You guys ROCK!

  3. I have this dress but only wore it once with a thin leopard belt. I find it difficult to style in a warmer climate where I live. Any ideas?

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