Brrr! Baby, it’s cold outside. So if I’m putting on a dress these days, it’s pretty much only a sweater dress. I love a sweater dress for a cozy but sophisticated look. In fact, I wore a beautiful ivory sweater dress when James and I exited our wedding reception 37 years ago, heading for our honeymoon. Today I’m continuing our year-long style series, Styling the Classics…for the Modern Woman, with two takes on the classic sweater dress.
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I won’t necessarily call out every item I show today so that I can focus on styling. But you’ll find links to anything that is available in the captions of the photos. Everything here runs true to size unless I tell you otherwise. I’m 5’8″ and about 160 pounds. I wear a size 10 or medium misses. I have an hourglass shape and even proportions. Hopefully that will help you know what you’re looking at here. Let’s check out how I’ve styled two sweater dresses from Ann Taylor, where you’ll get some great savings today through January 20th. Yay!
For the most modern look with a sweater dress, I really do suggest knee high boots. However, you can wear a sweater dress with a simple heel or flat, too. Depending on the event, your personal style aesthetic and the style of the dress, choose your footwear to suit.
By the way, this luscious wrap sweater dress is also available in butter pecan mélange, a soft taupe. I think the key to buying the right sweater dress is to look for one with a beautiful drape. You want something that skims your body, but not something that is too tight. This lovely sweater dress is 40% off right now.
One of the problems we sometimes run into with a sweater dress is they can look long and undefined. But both of the dresses I’m showing today have well-defined waistlines. Especially if you are not extremely slender (as I am not), I think it’s smart to look for a sweater dress with some definition.
I definitely wear shapewear under my sweater dresses. This high waist mid thigh short will give you great coverage in all the key places without creating additional unsightly lines and bulges. I always size up in shapewear to a large.
I wore fine fishnet tights here, but you could also wear tights in the color of your boots. That would look especially nice since this dress does have a slit in the side. I’m also wearing a slip, which is especially important when wearing a sweater dress with tights of any kind, so that the dress hangs right while you walk. Mine is old, but similar to this one. For some reason it is very difficult to find slips these days!
I definitely prefer the above look with boots over the heels. What do you think? My Ally chocolate brown boots are so comfortable, I ordered a pair of black ones, too. Use their size guide for the best fit.
My second sweater dress is also from Ann Taylor, but it is only 25% off. This ribbed waist sweater dress is a little sportier and more cheerful. While the other dress is very sophisticated and perfect for a winter evening out, this balmy blue dress is great for daytime.
Again I think the best way to style this dress is with boots. But another fun option, especially if you live somewhere warmer, would be to wear sneakers with this dress for a day of sightseeing or shopping.
Really, most sweater dresses that I’m familiar with keep their value year after year. I could absolutely still wear the dress I wore to depart on my honeymoon tomorrow…if I could still fit in it! It was a classic sheath sweater dress with a cowlneck and tie sash. Just lovely! Just for the fun of it, let’s take a look at a couple of the sweater dresses I’ve shown here in years past and see if I would style them differently.
The beautiful green dress above was a favorite. I ended up selling it to a reader who desperately wanted it, or I’d still have it. (And no, I don’t make a practice of that. Ha!) I think the only thing I’d do differently today would be to wear my new slimmer heeled brown Ally boots instead of those chunky stacked heels. And here’s one from even further back.
The sweater dress above is a donegal knit, and I haven’t seen as many of those this year. But I would definitely still wear this if you love it. And the only thing I’d do different is choose a more compact shoulder bag and a different necklace…or no necklace at all.
My assistant Lucy has also put together some style boards for further inspiration.
Above we’ve created a column of black under a grey wrap coat. Of course, once you remove the coat you have a chic all black look. We accessorized with impactful, but simple gold jewelry. Unfortunately that dress is about sold out, but it gives you an idea for how to style the black sweater dress you may have in your closet. Below we’ve created a lovely look with a lighter weight dusty blue sweater dress from Talbots’ new collection.
The blue shoes shown with the dress are definitely an option, but I prefer the nude slingback pumps. Add that beautiful neutral colored double-faced wool coat and you have such a cohesive outfit. By the way, that blue sweater dress is made from a soft ribbed knit, so many of us could wear it into the spring.
You can shop these two style boards and the outfits I’ve modeled above in the shopping widget below. But I’ve also rounded up other beautiful sweater dresses for you to peruse. Many of these are marked down significantly; I found a couple for less than $30! Thanks so much for stopping in.
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Blessed for My Day
Have you ever felt captive to a bad habit or a secret sin? I’ve been there! And the longer we are chained to that secret or hangup, the tighter grip it gets on us. We begin to feel like we could never tell anyone about our issue, much less seek help from anyone.
But that’s a lie from the enemy. The key to being released from anything that grips you is the truth. When we speak the truth first to ourselves, then to someone who loves us, we put the key in the lock and it begins to turn. And when we get real with the Lord, confess our sins and allow Him to show us the path to freedom, those chains begin to drop off completely. Truth may seem scary, but indeed it is the key to freedom.
To the Jews who had believed him, Jesus said, “If you hold to my teaching, you are really my disciples. Then you will know the truth, and the truth will set you free.” ~ John 8:31-32
I love a sweater dress, but how does one address the issue of static that can ruin a beautiful sweater dress outfit – even with an appropriate slip? Thank you. I am so grateful, Kay, for your blog and your youtube channel.
I keep a dryer sheet or two with me when I get out and about. And spraying underneath with some hairspray also works.
Thank you. Great ideas.
Love the blue sweater dress and I love the idea of tenniesfor a walk around day. I have a black sweater dress that still has a modern vibe even though I’ve had it for years
I had already ordered the Balmy Blue and just received it. Interesting fit. On the model and on you the waist is, well, at the waist, It fits me with the waist just under the boobs and looks like an empire style. My husband thinks it looks good without realizing it is not hitting me as designed. I am torn between keeping it or returning it for a larger size in hopes that the waist will hit properly. This is my life as a long waisted, busty size 10. Should I try the larger size…your thoughts.
I don’t know. That really does show that proportions and shape make a big difference. I actually have to pull the waist up to sit on my hips right. If you are long in the torso I’m not sure the next size will help. But if the fit is due to your bust, it would be worth a try.
Thanks so much for showing in your widget sweater dresses that hit the knee with boots that show some leg. At 5’4” the dress covering the boot look is too much for me and wearing a short wedge bootie with matching tights seems to cut me in 1/2 instead of making legs look longer. Thoughts? Also how do you keep the hem edge of your sweater dress from rolling? Thanks
The purple sweater dress is absolutely stunning and looks amazing on you. I hope you own it!
Sweater dresses and tall boots were made for each other! Always a chic look!
I am enjoying this series. Will you be doing one on how to style an A-line skirt? I find them very hard to style without looking frumpy but I think the shape is flattering to most people.
I love the wrap sweater dress and definitely with the boots! For me it would be better if it didn’t have drop shoulders but what a gorgeous dress!
Kay I didn’t know you had really long hair in 2018. It was very pretty. It’s a really nice photo of you. Sweater dresses aren’t for me because the only chance I would get to wear one is to church. In Texas I don’t know if it will be cold enough to wear. This January has been colder but the year I owned one sweater dress it never got cold on Sundays.