How To Wear Dresses in Winter


Whether you’re an ultrafeminine woman or looking to play up your feminine side, a dress is one of the perfect ways to make your wardrobe lean toward all things dainty and frilly. Yet, it can be understandably challenging to figure out how to wear dresses along with items like everyday leggings during the winter to keep you warm. Our team at Leonisa understands the challenge. This is why we’re here to help you out with switching up your winter wardrobe this year. To successfully conquer this fashion challenge without catching a cold, consider the following tips.

Incorporate the Right Undergarments


When some people think about tights, they often imagine the thick, opaque ones that little girls used to wear to church. While we believe there’s still room for those types of tights, there are now many more fashion-forward options to consider. For instance, choose tights that feature various prints and patterns. Purchase tights that have a thicker texture to feel warmer and more protected. To make it stylish, you can opt for different colors of opaque tights. If you’re wearing an all-black outfit and you want to add a pop of color, you can incorporate a pair of gray opaque tights. If you like bright colors, look for a thick pair of yellow opaque tights. When matched with some boots or sneakers, opaque tights provide visual interest while keeping you warm during winter. There’s also the classic flesh-toned tights that a lot of women reach for during the wintertime. However, be sure to pick the right option for your skin tone to provide the barely there appeal.

Thermal Underwear

Thermal underwear can indeed be a wise investment, especially in cold weather, as it helps keep your body warm by trapping heat. In learning how to wear dresses in winter, one of the key tricks we recommend involves ensuring the thermal underwear is snug instead of tight. The idea is to create a thermal barrier without restricting your movement. Pay attention to cuffs around your wrists and ankles to prevent cold air from entering. Choosing the right materials is also crucial. Look for thermal underwear made from high-quality materials like merino wool, silk or synthetic fabrics designed for warmth and moisture-wicking properties. The material should be comfortable against your skin. While trapping heat is essential, it’s important that the thermal underwear allows your skin to breathe to prevent excessive sweating and discomfort. Choose the option that best suits your needs and activities. Separates can be more convenient if you anticipate needing to use the restroom or change during the day.


While shapewear is often associated with creating the look of a specific body shape or a more polished appearance, we know it can also help with warmth and comfort when you’re wearing a dress during the winter months. Because of its coverage and tight fit, shapewear can act as an additional layer of insulation under your clothing. This can help you stay warmer in cold weather by trapping body heat. It can even help smooth out any visible lines under your dress. This is particularly useful when you’re wearing fitted or clingy winter attire. Similar to thermal underwear, our shapewear can be a great base layer. Without making you look lumpy or bulky, it can provide an extra barrier against the cold. When selecting shapewear for winter, consider the material. Opt for options made from warmer, moisture-wicking and breathable fabrics that can enhance comfort and insulation. Make sure that the shapewear you choose is comfortable to wear for extended periods. It should provide support without causing discomfort or restricting your movement. Remember to choose the correct size so that the shapewear fits well and does not cause bulging or discomfort. Ill-fitting shapewear is counterproductive.


Wear Layers


Layering a dress with a blazer is a dynamic way to achieve a professional and feminine look. The blazer adds a touch of sophistication to your outfit while the dress can bring out your femininity. When selecting a dress to layer with a blazer, consider the setting. For the workplace, classic styles like shift dresses, sheath dresses or wrap dresses are often good choices. Ensure your blazer is well-tailored and fits you perfectly. A well-fitted blazer enhances your overall appearance and gives you a polished look. Consider having it professionally tailored to achieve the ideal fit. Oversized blazers are currently stylish and can provide a unique and fashion-forward look. However, be mindful of the proportion. If you choose an oversized blazer, balance it with a well-fitted dress or other clothing items to avoid looking too baggy.

Sweaters and Sweatshirts

Layering sweaters or sweatshirts over a dress is a versatile and stylish way to adapt your outfit for various occasions.

  • Button-Down Cardigan or Grandfather-Style Sweater: For a more formal brunch with friends, pair your dress with a button-down cardigan or a grandfather-style button-down sweater. These sweaters provide warmth and style, giving you a polished and elegant appearance. They work well with a variety of dress styles from A-line to wrap dresses.
  • Graphic Sweatshirt and Denim Dress: Pair a graphic sweatshirt with a denim mini dress for a trendy and edgy look. Add a belt to cinch the waist if you want to create more definition. Finish the outfit with ankle boots or sneakers for a cool and comfortable ensemble.
  • Hoodie and Dress: Layering a hoodie over your dress, whether it’s a casual T-shirt dress or a more structured one, can create a relaxed, urban vibe. Add mid-top sneakers or high-top sneakers for an effortlessly chic appearance.



Vests can be a valuable addition to your winter wardrobe as they offer flexibility and style. Whether for the workplace, outdoor activities or repurposing summer dresses, vests can help you stay warm and fashionable. By carefully selecting the right vest and coordinating it with your outfit, you can create fashion-forward yet practical looks for various occasions. Begin to collect structured vests, puffer vests and sweater vests to match with your winter dresses.


Layer turtlenecks under jumper-style dresses, overall dresses or pinafore dresses. Turtlenecks provide extra warmth and add a fashionable touch to your outfit. Choose classic colors like black, navy blue and gray. These neutral shades can easily complement a wide range of dress colors. This makes them a perfect wardrobe staple. Remember that fabric matters. Select turtlenecks made from warm and comfortable fabrics like wool, cashmere or a blend of materials. These materials offer excellent insulation and ensure you stay cozy in colder weather. When layering a turtleneck under your dress, make sure it’s not too bulky. A slim-fitting turtleneck will provide warmth without adding excess bulk, allowing the dress to fit properly over it. When you’re wearing slim-fitting turtlenecks, it’s easier to seamlessly wear body shapers underneath to complete a sleek aesthetic.

Choose the Right Materials and Fabrics

Transitioning your wardrobe for colder weather is essential for staying warm and comfortable during the winter months. When you’re selecting winter dresses and incorporating them into your winter wardrobe, opt for thicker materials such as wool, cashmere, corduroy and flannel. These fabrics provide better insulation against the cold. Reach for dresses with long sleeves or three-quarter sleeves to keep your arms warm. Sleeveless or short-sleeved dresses can still work in winter when layered with cardigans or jackets.

Wear Protective Footwear

When the temperature drops, keeping your extremities protected becomes a top priority. Although dresses may not immediately come to mind when you think of cold-weather clothing, it is still possible to stay warm while maintaining your fashion sense. Investing in a variety of boots is a great place to start. Look for different finishes such as leather or suede. Aim for neutral colors to increase versatility. For midi-length dresses, try pairing them with ankle boots for a fun and practical look. Knee-length or thigh-high boots are great options for maxi and mini dresses as they provide ample coverage. Even sneakers can be paired with dresses for a comfortable yet stylish option. There are plenty of fashionable and comfortable sneaker options available that can be worn year-round. Regardless of the type of footwear you choose, always prioritize comfort. Adding insoles can help keep your feet cozy and cushioned especially if you’ll be walking long distances in the cold. Remember, when it comes to staying warm, comfort is vital.

Invest in High-Quality Outerwear and Coats

Shopping for a winter coat that complements your winter dress goals is a great idea. When you’re on the hunt for a winter coat, prioritize length. Consider a coat that falls at least to your shins or ankles. A longer coat provides better coverage and insulation, keeping your legs and dresses warmer. It also offers a more elegant and sophisticated look. Invest in a high-quality winter coat made from materials like cashmere, wool or down. These materials are excellent insulators, providing warmth and comfort. Wool and cashmere coats are often both stylish and warm while down coats offer excellent insulation. Look for coats with proper insulation, such as a warm lining or down-filling. Ensure that the coat is designed to keep you warm in freezing temperatures. Consider a winter coat that is windproof and waterproof and has a high collar or a hood for added protection against the elements. These features will keep you dry and cozy in winter conditions. Choose a coat in a versatile color and style that can be paired with a variety of winter dresses and outfits. Neutrals like black, gray or camel are classic choices that work well with many colors. Proper care and maintenance of your coat, such as regular cleaning and storage, will extend its life span and ensure it continues to keep you warm in the winters to come.


Fine-Tune the Process

At first, some of these tasks might feel tedious. At Leonisa, we encourage women to fight through the temptation to do what might seem customary at the moment. On a cold morning, it might be normal for you to throw on a pair of sweats instead of a dress. However, once you’ve found the right dresses and the right undergarments, the rest of the process becomes effortless. You deserve to look and feel your best. In the winter months, when it’s tempting to dress for comfort, don’t forget to include style in the equation. By stylishly wearing winter dresses, you can develop an iconic aesthetic and wardrobe that will carry you for years to come.

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