Chic-But-Comfy: 6 Flattering Midi Dresses Styled For The Holidays

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Stretchy fabric. Stretchy fabric is what we want this year, especially during the holidays.

Stretchy fabric doesn’t always have to mean leggings and sweatpants, though, and I’m finding myself wanting a departure from the two sometimes. Not all the time, mind you, but sometimes. Just to feel a little normal and a little fancy. You might not think it, but occasionally I like to dress in ‘my version’ of fancy.

Chic & Comfortable: 6 Stretchy Midi Dresses To Wear For The Holidays

Midi dresses are my favorite for flattering a shorter figure and showing off curves. I tried out a few that were currently catching my eye. All of these are super-comfy, stretchy, chic…and perfect for the 2020 holidays.

Ruched Midi Dress – Michael Stars

at Nordstrom | at Amazon

This is so cute, flattering and comfy. It’s fitted, but easy to get on and not restricting. It’s amazing. I had to brighten my photos because it was dark this day, so the color is a little darker than it looks here…definitely a navy in person. It also comes in a few other shades, too. SO. so good. This is why it’s first!

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (s, nocturnal) | boots (similar or these)


Front Button Long Sleeve Midi Dress – Fraiche by J

This dress is so cute and almost a totally different vibe than the one above. The material isn’t quite as luxe, but I love how comfy this dress is, how the neck comes up a bit and the button detail. This one is ribbed and soft, but not actually bodycon or overly stretchy. It just lays nicely though and is a solid choice. I think the buttons might allow this one to be worn over jeans or pants, too. I am not totally familiar with this brand, but after trying this dress I want to try more.

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (s) | boots (similar or these)


Jolie Textured Mock-Neck Dress – French Connection

at Nordstrom | at Bloomingdale’s (more sizes in stock)

Ooh la la. Leave it to French Connection. Love. This one is a true bodycon, but in a really great slightly thicker knit with these cool ribbing details that are so flattering. This shade is a blue black, and again a little lighter in my pictures here, but definitely blue-leaning instead of solid black. That made me unsure about it, but I keep looking and thinking this might be the winner for me.

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (m) | boots (tts)


Sweater Midi – J.Crew

This one I found in my recent J.Crew try-on sesh, but too good not to include again, especially since it seems to be back in stock, in black at least. SO comfy. Probably the comfiest of the bunch, but perhaps a bit more inclined to stretch out a little, but maybe that’s not a bad thing when it comes to 2020 holidays? Heh.

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (s) | boots (similar or these)


Rib Knit Tie-Waist Dress – Topshop

This one is really cute. I love the tie waist for a flattering nip in there without being restricting. It’s also forgiving on the ol’ tum area. I really like this one. These are all making it hard to decide which I’ll keep to wear for my comfy-chic holidays this year!

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (US 8, fits like a 6-8) | boots (similar or these)


Honey Lips Midi Sweater Dress – Roxy

This one was really good, too. More of a stretch rib and slightly heavier like the French Connection dress. It feels like it would hold it’s shape well, and I love the sleeve length and side slit. See how there is no clear winner here because they’re all good?

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (m) | boots (similar or these)


Style Your Favorite Midi Dress With…

…A Moto Jacket & Taupe Boots

Definitely the most ‘me’ combo. I swear I cannot style a dress without first always trying my moto jacket. It’s just always my favorite because it makes any dress badass. It’s also flattering for those of us with hips, to have a jacket that hits right at the waist OR well below. A blazer or hip-length jacket just wouldn’t have the same flattering look. A knit moto would also be great here if you’re hoping for optimal comfort.

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

jacket (US6) | dress (s) | boots (similar or these)

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

jacket (US6) | dress (s) | boots (similar or these)


…White Ankle Booties

OK, so I probs should have thrown on my favorite long camel cardigan over this, but I forgot. Pretend it’s there and you have a cute cozy outfit with the fresh mod-ish vibe of a white boot.

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

dress (m) | boots (size up 1/2 size)


A Faux Fur & Suede Boots

So, this is cozy. And it looks chic! That’s what we’re going for here…comfy but a little fancy, so it feels like a holiday during normal times, a bit. Put on something fancy at least once this holiday season. I may start wearing this faux fur with my sweats, too. All in, baby…

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

jacket (s) | dress (s) | boots (similar or these)


Shop Comfy Midi Dresses

Help me decide! Which dress??? I definitely want but do not need them all. I only wear a dress a few times a year, but if I do wear one it’s usually this style. The Good American one I found this winter is KILLER but also a little killer to put on. These are all 2020 pandemic-unpredictability year friendly…

xo,

L

Hey, hey from Portland, OR. Would love for you to follow me over on Instagram @laurajansenstyle for all things casual mom-wear, lots of foodie pics and donuts, some kitchen dance parties and some social justice. xo

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P.S. This one’s for the Pinners…

Midi dresses are stretchy, flattering & sexy. We're styling 6 — long sleeve, short sleeve, knit, comfy & chic that pair perfectly w/boots (or not).

2 COMMENTS

  1. Ok, I WANT a comfy cozy knit dress…but I have zero hips and every single dress I try on has the hips constructed in (for lack of a better description). Why can’t they just flow with the body?? Why the pre-cut hips? For those of us with NO hips at all. Sad. Any suggestions for this issue?? 🙂 Thank you!!!

    • Ahh good question! I’m not sure. I think it’s like bust darts for boobs…that is my theory without being a clothing designer. But yes that would be so annoying. Have you tried any from J.Crew? I find their stuff in general to fit more straight. Perhaps a place to start!

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