Cooler weather doesn’t mean forgetting about all those beautiful dresses in your closet. In fact, when the weather’s frosty, you have more options for presenting dresses in new and exciting ways. The key to doing that is layering.
Let’s review 5 ways to wear dresses in cooler weather while keeping your cozy comfort in mind.
1. The Right Dress
Cooler weather tends to discourage women from wearing dresses but any weather is the right weather for a dress. Considering the dress you’re thinking of wearing as the foundation for your look.
A cotton sundress is a very different animal than a sweater dress, so as you tease out ideas for wearing a favorite frock in cooler temperatures, ask yourself some simple questions:
- Does a jacket look right with that dress? Women’s luxury jackets to wear over your dress need to be the right length and fabric weight to create a coherent look.
- Will tights or patterned hose work with the dress or look awkward?
- Will layering a blouse or sweater underneath the dress affect the fit?

The cotton sundress or sweater dress dichotomy is the most obvious example. But choose dresses that lend themselves to layering, without looking like you’re forcing the issue. For example, cheesecloth dresses and winter weather are not a good match. Choose dresses made from heavier fabrics.
2. The Right Boot
Remember proportion when choosing the style of boot you plan to wear with your dress. For example, an ankle bootie or a grunge-look combat style boot both look great with mid-thigh or minidress hems. But for longer dresses (knee-length and midi), you’ll want a knee-length or over-the-knee boot.
Getting the proportion right goes hand in hand with getting the texture and weight of your dress and boot combination right. For example, heavy, chunky-heeled boots are not going to work if you’re wearing a dress that’s fitted close to the body with elegant lines, or a lightweight, flowing dress.
And some boots are not intended to be worn with dresses at all. Take care when matching dresses to boots, checking that the proportions are right between where the hem of your dress ends and the boots start. Getting it wrong can drag down the whole look, so experiment with different combinations to get it right!
3. Layer Invisibly

Layering is a great way to look stylish while staying warm. Inner layers are thinner, with a coat or jacket in a heavier material on top of everything to trap warmth. And you can layer invisibly too.
Nobody needs to know you’re wearing a long sleeve t-shirt under that long sleeve dress. You may even be wearing leggings for all anyone knows! So long as you have on a pair of knee-length boots, no one’s the wiser! Even thermal undergarments can be worn with the right styling, keeping your private, cool weather warming offensive completely (and literally) under wraps! You can even find quality fleece-lined leggings and jeans now, so when you step out looking winter-sleek, fleece is your little secret.
4. The Right Topper
For the money, a midi-length coat is your best bet for cooler weather. A cropped or hip-length coat may appeal but if you’re hoping to keep warm, leaving half of you exposed to the elements isn’t a great strategy.
Seek out coats that finish about mid-calf in textured fabrics like boucle or wool. An ankle-length opera coat is striking but if it snows where you live, that stunning coat will get wet around the hem, so style yourself with an awareness of street-level weather realities. Another advantage to a mid-calf length coat is that its proportions work with everything you own, from dress pants to jeans to dresses. Versatility matters as much as coverage, if your winter wardrobe revolves around one stalwart piece of outerwear.
5. Warm Head = Happy Camper!
Don’t forget that most of your body heat exits from the top of your head, so it makes sense to wear a hat. The popular knit beanie doesn’t really lend itself to more professional or formal looks, so when you’re dressed for work or an evening out, choose a colorful felt beret or a chic crochet cloche to keep the heat in with style.
You most certainly can wear dresses when the temperature dips! With a little clever styling and the use of layers, your beloved dresses take on a whole new fashion life, lighting up the winter gloom.



