Over the past several years, I have completely fallen in love with dark floral dresses for winter and fall. this season, I ordered a few options to try and couldn’t wait to share them with you! From a wedding-friendly option to more casual everyday options, I have a variety of dark floral dresses for winter!
What makes a dark floral dress so special in my book? Even though, they’ve risen in popularity, wearing floral print in cooler weather still feels unexpected. They add a little femininity to my wardrobe in a time of year when I lean more towards classic tailored layers. But I also love them because of how well they pair with edgier details like leather accessories and heavier boots.
Dark Floral Dresses for Winter
My Sizing
For reference, I’m 5’7 1/2″ with a short torso and very long legs! I typically wear a 29 in jeans or a size 8. My bra size is a 36C, and I typically wear a size medium (or 8) top.
If you ever have any question about what size I’m wearing, check the links below each image! I list any recommendations I have for sizing up or down for quick reference. (TTS= true to size!) For full details, I’ll be chatting all about quality, style, and fit in the paragraphs above each photo. Let’s go!
Dark Floral Maxi Dress
If you have a winter wedding on your schedule, this floral maxi dress is my top recommendation. It is absolutely stunning in person. The fabric is a heavyweight textured cotton. It’s fully lined, has pockets, and has a smocked panel in the back! I would recommend sizing down one. I’m in a medium, but the fit is generous. I would prefer a small. If floral isn’t your thing, it also comes in a zebra print and solid red.

V-Neck Floral Maxi Dress
With a relaxed boho vibe, this a-line maxi is perfect for everyday wear. The top is button-front with a drawstring waist with tassel detail. I love the mix of floral prints on the tiered skirt and sleeves. The skirt is also fully-lined! If you love this cut, there are six different dark floral prints to chose from! I recommend sizing up one. I’m in a large.

V-Neck Shirred Midi Dress
If you’re looking for an affordable option, this is it! The bodice is smocked and creates a bit of a fit and flare fit! The skirt has a ruffle tier and it also has pockets! I’m in a medium and find that it fits true to size. It also comes in a solid clip dot. Currently 40% off!

Square Neck Tiered Maxi
I hate to pick favorites, but this easy midi tops my list! I love the relaxed fit and tiered skirt. The color is also beautiful in person with a mix of burgundy, brown, and lavender! You might recognize it from my fall try on post or Instagram, where I wore it layered with a cardigan! I’m in an 8 but could have easily sized down one. If you are bustier, stay true to size. The fabric has zero stretch.

Boho Maxi Dress
With a relaxed fit, billowy cut, and tiered skirt, this dress is the answer to all my boho dress dreams. The floral on my exact dress is a mix of cream, blue, brown, and orange, but it also comes in several other color ways. I sized down one and like the fit! The lining is more form-fitting, so keep that in mind, but the outer layer has plenty of space! This could make a beautiful maternity option if you swapped out the slip for something with stretch!

Shop Dark Floral Dresses for Winter
Want even more dark floral dress options?! Here are a few that have caught my eye lately!
