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Weekend Inspiration: Date Night Jumpsuit

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If you’ve been considering a jumpsuit but not sure if you can pull it off, I hope today’s post convinces you to give one a try. I was also hesitant, mostly because of my height. I’m 5’10, so I figured the fit would be awkward, and the length would be too short overall.  

To my delight, I was wrong and now own not one, not two but three different black jumpsuits. I thought it would be helpful to see a normal person in one, with fit issues like everyone else and a lifestyle that doesn’t require getting dressed up for most occasions. 

A couple weeks ago, after a long few days with the kids and an overwhelming week of work, Bri and I found ourselves with a rare opportunity for a spontaneous date night. I should say, I’m not starved for a night out, but it’s always pre-planned with our sitter lined up well in advance. There’s something fun and almost nostalgic when one is dropped in our lap.

So when Bri grabbed a reservation and asked if I could be ready in 15 minutes, I knew just what to wear. The jumpsuit I turn to the most is this Vince Camuto tie-waist option we’ve featured here a few times. I wear it often, because it feels special without being fussy.

I am wearing my usual size 8 in this, which fits perfectly without a bit of alterations – always a bonus.

Date Night Jumpsuit

Weekend Inspiration: Date Night JumpsuitJumpsuit: $99, similar style for plus here.  Block Heel Sandal similar here.

First, the v neckline is super flattering and modest. Why v necks are cut down to the navel these days is beyond me. Plus, you can wear your favorite everyday bra. No need for some special contraption you’re only going to wear a handful of times.

I have, let’s say, a substantial booty, which, I’m not mad at thanks to years of squats. Usually, if I do have to size up in something, it’s to get it over my rear, but this fit is very comfortable and flattering. Because I am fuller on the bottom I tend to avoid wide leg pants, but here, the cut is on point and helps minimize the waist.  

The length is just enough for me to wear about a two inch heel or a pair of flats sandal. I prefer a heel with a wide leg to help balance out the look. If you are any shorter than me, consider your preferred heel height and have the pants hemmed from there. 

Classic Clutch and Simple Jewelry 

Weekend Inspiration: Date Night Jumpsuitsimilar clutch here

This clutch is one of my favorite purchases from Henri Bendel, which sadly went out of business at the end of 2018. I splurged on it, but every time I carry it, I’m reminded of how important it is to invest in certain classic pieces occasionally. For a similar style and price point I like this Gigi New York Croco Clutch

Carry anything you like, and dress it up or down with accessories. You’ll see I tend to keep things simple and wear my better jewelry every day. I figure why wait for a special occasion?

Date Night Ready in 15 Minutes

Weekend Inspiration: Date Night Jumpsuit

The tie waist is a lovely detail, it kind of mimics a wrap dress. I like it this way in the summer since it feels light, but would wear a leather belt in the fall to add a layer and interest. Something like this would be super cool

Speaking of the fall, carry this right into the new season by changing out the shoe to an interesting pump (I like these on sale at DSW), and add a blazer. You’ll look just as chic and seasonally appropriate. 

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Weekend Inspiration: Date Night Jumpsuit

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Monday 12th of August 2019

The jumpsuit looks great on you! I would like to try a jumpsuit but I am much shorter and with a pear like figure.


Sunday 11th of August 2019

You look so pretty! I love this on you and I love how your accessories are simple so your beautiful hair and lovely skin stand out. Well done!,

Megan Kristel

Thursday 15th of August 2019

Thanks Carol!


Friday 9th of August 2019

I am hesitant to try jumpsuits for the purely practical reason of struggling in the restroom. They seem difficult to manage in a tight space.

Megan Kristel

Thursday 15th of August 2019

Maybe I'm just used to things being a little extra, but running to the restroom in this doesn't bother me at all.


Friday 9th of August 2019

I bought it also and love it! I never thought about the jean jacket!! Totally going to try that! Thanks!

Valerie Swearingen

Friday 9th of August 2019

I bought this when you recommended it awhile ago and absolutely LOVE it! The material is heavy enough to drape properly (and cover any lumps ;), but not too heavy that you can't wear it in the summer. I wore mine to a super fancy event in DC and then put a jean jacket on over the top and swapped heels for sandals to walk around the rest of the day. So cute!!! I wish I could add a pic to show another "normal person" in an outfit that Megan has recommended. It honestly is a great staple piece to have in a closet. Excellent reco!!

Megan Kristel

Thursday 15th of August 2019

Thanks so much Valerie! I love the fabric too - perfect weight to give some structure but still drape nicely.

Elle D.

Friday 9th of August 2019

This is super cute but I'm alwys hesitant to buy dry-clean only items... how do you handle this in your house? Do you have a home solution or do you have a trusted local dry cleaner?

Megan Kristel

Thursday 15th of August 2019

Hey Elle, Admittedly, I dry clean a lot. We have a local dry cleaner we've been using for years who takes good care of our things. They give a discount for dropping off on certain days but we've used them for so long they give it to us whenever we drop off. That helps a bit because it certainly adds up.