Everyone always talks about making your dresses work as the temps drop from summer to fall…but what about when the temps plummet from fall to winter? A measly pair of tights and a denim jacket—though supes cute—are not going to cut it for this New England gal. But that doesn’t mean you have to stash the dresses away completely! You can still make them work with some strategic and, shall we say, more involved layering. The overall goal is to cover as much of yourself as possible while still visually breaking up your body so that your look is streamlined, not frumpy. We want to be warm, not swimming in our clothing. Absolutely no shade because I actually love their style, but we are NOT trying to look like the Olsen twins at NYU circa 2005. You know what I’m talking about…
Honestly, I think sometimes people get nervous about the idea of layering when it comes to dresses. Maybe it’s because you don’t see it done as often, causing people to worry they’ll get it “wrong.” Or maybe it’s because dresses are often depicted as “one and done” items that require very little styling. Dress is on the right way? Check. You have something on your feet? Check. You’re good to go.
But regardless of the reason…where’s the fun in that?!
If you continue to view dresses as strictly summer wear or a one-stop outfit shop, you are completely missing out on their amazing versatility. Not only are you limiting your overall outfit options, but your depriving yourself of the chance to get creative and experiment with your personal style. In today’s blog post, I’ve showcased two completely different looks using my three-step approach for wearing dresses in the winter in the hope that it will inspire you to give these guys a little love from December through March.
1. Tall Boots Are Your Best Friend.
Sorry y’all, but long gone are the dainty ankle booties of autumn. As I mentioned earlier, the goal here is to cover as much of your body as possible, so we want a boot that goes to at least your knee. If you’re going to be in a more conservative setting—say the office—or if your dress hits at midthigh or longer, I’d stick with a knee-high boot to keep things polished. Otherwise, get yourself a great over-the-knee pair. Not only are they super on trend (important), but you’re going to get serious leg coverage, which is key to staying warm (more important).
The other great thing about tall boots?? Socks! Because there’s no way your socks will be exposed, you can—and absolutely should—wear the warmest, chunkiest socks you can find to keep those toesies toasty. If you’re in over-the-knee boots, obviously anything goes. If you’re rocking knee-high boots, I highly recommend letting a pair of cute boot socks peek out the top like I did on the right. Not only will this visually add more dimension to your look, but it’s an extra layer—even if it is only on your calves. As someone who is literally always cold, I will literally take anything I can get.
2. Think Light Layers Under, Heavy Layers Over.
Now, I’m sure this step doesn’t seem like rocket science…and you’re absolutely correct, it’s not. Basically, your “under” items should consist of thinner materials and your “over” items should be thicker. While there really isn’t much more to it than that, there are a few things I wanted to briefly touch on that might be helpful when thinking through your own layers.
You’ll notice that the opaqueness of the black layer on my legs is different in these two photos—that’s because I’m wearing tights under the leopard dress and actual cotton leggings under the striped one. Normally I would say cotton leggings are going to be too thick to layer under a dress, as their bulkiness may peak through in an unflattering way. However, if the piece you are layering over said dress fits longer and looser—say a long fur vest; a chunky, oversized cardigan; or a longer utility jacket—any bulkiness caused by the thicker legging is going to be hidden anyway. If I’m not wearing the vest, the waistband of my leggings is totally visible from the back of this striped dress due to both its color and body-con fit. But, with my tush completely covered, this becomes a non-issue. Another win for #teamwarm.
Similarly, don’t be afraid to double up on your under layers. I bet—and by “bet” I really mean “know”— you can’t tell from the picture, but I actually have two tops on underneath the leopard print dress. The first is a thin, body-skimming thermal, which I followed up with the black turtleneck. It sounds silly, but even just that one extra layer can make all the difference in your overall comfort level when it’s chilly. Confession: I almost always layer a thin, long-sleeved bodysuit or tee under my sweaters for extra warmth. It is literally my saving grace all winter long. As long as no one can tell, it’s your cozy little secret, right? Well, I guess technically now that I told you it’s no longer a secret…but you know what I mean.
3. Tack on some extras to up the warmth factor.
And now, the really fun part: styling for warmth—both components of which are up there on my list of favorite things. The point here is almost to demonstrate to the world that you recognize it’s, quite literally, freezing out, but you’ve got it covered (i.e., completely appropriately dressed for the elements). Play into the season by accessorizing with winter-specific items (think scarves and hats [like I did in the picture on the right]) or just add another layer of outerwear. A leather jacket (as I did on the left) or blazer are great options if you want to keep the look a bit dressier. Thinking more casual-cool? A varsity jacket, cropped puffer, or bomber jacket would be adorbs.
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What do you guys think about wearing dresses in the winter? Have I convinced you that it’s possible to make these guys work in a way where you look good and feel good? I hope so! Thanks so much for stopping by!