I was trying to find a wintertime equivalent for the easy black midi dress I live in all summer — you know, like this. The one I throw on with sneakers and sandals and — heck — even flip flops? The type of dress that is mostly casual, yet automatically looks a little bit fancy, just because it’s longish and black and that’s how these things go.

Well…I was thrilled to find several solid options that work for winter (skip to the end to see them all), but there was one in particular I couldn’t resist. It’s the type of dress that’s sexy enough for even a fancy date night…but can easily be dressed down for everyday. Even better? It’s sustainably made.

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | tee (small) | boots | similar bags 1, 2 and 3


The Classy & Casual Black Dress I’m Loving For Everyday

Reformation Dillon Ribbed Long-Sleeve Midi Dress

Reformation doesn’t mess around when it comes to slits up the leg — it’s one of the reasons I love them. Add in the extra-long sleeves, and soft, ribbed fabric, and I’m sold.

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | boots (60% off!!) | similar bags 1, 2 and 3

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

I always go up one size in Reformation dresses, and this particular one is fitted enough (definitely a bodycon dress) that I typically layer it over this Commando slip. The slip is comfy to wear, smooths nicely and adds some extra warmth, too.

NOTE: Because so many of my fav dresses have a long leg slit, I ended up hemming the Commando slip shorter…but a taller mama might be fine. Or, simply fold the slip up — I did that a few times before eventually taking it to a tailor.

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | slip (small) – under the dress | boots (60% off!!) | similar bags 1, 2 and 3


Black Midi Dress Outfit Idea 1: Faux Fur Jacket + Western Boots

This is a very typical date-night outfit. One might even recognize most of it — I do wear the same stuff over & over, haha. But in general, if our date night involves a Lyft (rare), I’ll wear exciting shoes (like THESE OMG OMG OMG) but if we’re walking, then comfy, walkable boots are a must. And if it’s really cold, I’ll add pretty sheer tights (like these), a hat and mittens.

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.
Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.
Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | slip (small) – under the dress | boots (60% off!!) | similar bags 1, 2 and 3


Black Midi Dress Outfit Idea 2: Knotted Band Tee + Doc Martens

I typically don’t wear anything this bodycon during the day…but I’ve found that knotting a tee over a fitted dress basically transforms it. The dress then becomes so easy to wear (and the day-to-date-night potential is huge).

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | tee (small) | boots | similar bags 1, 2 and 3

Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.
Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.
Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.
Found: a black midi dress that's sexy enough for winter date night...but easily looks casual w/ Doc Martens & a t-shirt. By Reformation, a sustainable brand.

jacket (xs) | dress (small) | tee (small) | boots | similar bags 1, 2 and 3


Shop My Favorite Easy Winter Dresses (& All The Outfit Ideas I’m Wearing With Them….)

Everything mentioned in the post (even the random text links) can be found below. And…before I forget…that cream Treasure & Bond dress is actually available only as a dark gray. But it’s great. See our IG (@themomedit) for a few stories on how that dress looks on, and yet another way to style these easy winter dresses.

Also — we’ve been having some serious fun with our Nordstrom ‘Looks’ (think: shoppable collages with head-to-toe outfit ideas). You can find our most recent picks here or follow our Looks account to never miss the latest.

xo,

S

photo credits: Redfield Photography

A huge thank you to Nordstrom & ShopStyle for sponsoring this post! Nordstrom continues to be one of my very favorite places to shop (and I’ve really been loving the new Sustainable Style category, so thank you for that). As always, all thoughts, opinions and product choices are my own. And readers, thank you for your continuing support. It doesn’t go unnoticed and is so very much appreciated.

15 COMMENTS

    • I *think* so? I bought a similar dress last year (or year before? doesn’t matter) and it did come back into stock, although it may have sold out again pretty quickly. But I’ll try to keep an eye on this one…

    • It’s hit or miss. If it’s not too cold, or if we’re literally going from Lyft to restaurant (and back), then I can easily get away with the slit. If not, I add sheer(ish) tights. Like these: https://shopstyle.it/l/bcYa7

      (And frankly, those tights add juuuust enough warmth to wear during the day, too. For day, I’ll add socks and my Doc Martens.)

  1. I love a high slit but the only problem with doing it with a bodycon is that it pretty much rules out Spanx. Folding Spanx up usually creates a weird lump. Unless someone out there knows a trick??

  2. That dress is a cute fall dress for us Michigan folks. But it’s 13 degrees here today and ain’t no side slits happening. You look great though!

    • Soooo….I’m originally from the Upper Pennisula. 🙂 And FWIW, I wore a red dress very similar to this one while home in Marquette over the holidays. I wore it with sheer (ish) tights, black booties, a cozy sweater over top, and a huge puffer, hat, and mittens. Depending on the festivities, I was able to peel of layers as needed (the sweater stayed on for church because that drafty place is COLD, but came off for the party).

      For me, it’s all about the long-sleeves. Bare arms are tough in the winter.

  3. These looks are great on you! I don’t know if I could pull it off but I love the “one dress, two ways” posts to give ideas.

    I have a question though–can you go into what makes the Anine Bing shirts so good? I have been working toward buying fewer, but higher quality pieces, but I still balk a bit at a $100 t-shirt. What makes it worth the price, in your opinion?

    • I had resisted for a while, too, for the same reasons. But this darn tee just makes every outfit better. The fit is tomboyish without being unflattering, and the fabric is not thin and drapey…but neither is it stiff or scratchy or too thick. It’s that perfect middle ground. And the designs are all vaguely edgy without being any one thing (london punk in the 60? Harley davidson?) and it ends up being the thing I grab most of the time. Literally goes with everything.

  4. She must mean winter in the south somewhere. There is no one I know of who will rock this look in Duluth, MN in January…February, March or April for that matter!!

    • Oh hey Duluth!!! I’m originally from the UP (of MI) so…yeah. I remember being heartbroken almost every year because we usually had a snow day on the first day of Spring. 🙂 . Did you see my comment below about adding tights, a sweater, and a huge puffer coat? That worked for Marquette in December…but admittedly, it wasn’t great for walking through giant snow banks, haha. Definitely a ‘night out’ situation. I wonder if my wedge Sorels would work with this dress? Hmmmm….

  5. Those boots have been on my cart for weeks?? Can’t decide on chestnut or black aaaand ifI can pull off the look. I have never owned doc
    martens!

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