Winter Dresses: How to Wear Winter Dresses in a Fresh Way

Style Tip

A dress should be a no-brainer outfit, right? One and done, just throw it on and go! But it can be quite easy to get in a rut of wearing one the same way each time.

One of my favorite elements of being a Style Coach is teaching my clients how to create outfits in a variety of ways with the items they already own. This helps them avoid grabbing for the same ol’ thing every time! When it comes to winter dresses being creative is key!

I am sharing how to accessorize them to make them feel fun, what third pieces to add, and the various shoe options you can rock to create a variety of fresh winter outfits!

Cinch It

winter dresses

Photo Credit | Who What Wear

Style Tip: Cinch a more voluminous winter dress with a great leather (not patent) belt to create a more flattering silhouette (of course depending on YOUR body type; belts aren’t great for rectangles).  Also, if a dress comes with an inexpensive, patent belt then switch out that belt for a more supple leather for a more chic look.  Lastly, if you are more petite and want to wear a midi or longer length dress, then opt for a neutral bootie or shoe to prevent a choppy, and unflattering look.

Tonal Head to Toe

winter wear

Photo Credit | Teen Vogue

Style Tip: There’s nothing more in style or chic than pairing a midi dress with a pair of tall block heel (not flat) boots.  I love how she paired a boot in a richer brown tone with this dress for a lovely tonal appearance.

Rock Leather

winter clothes

Photo Credit |

Style Tip: Another example of how to pair a tall heeled boot with a longer length dress…a great way to stay warm and look chic!  You’ll notice that there’s no skin showing between the dress and the boot.  Also, a shorter tailored leather or suede jacket always looks cool as the third piece with a dress, and again keeps you warm!

Pop of Color

pop of color

Photo Credit | Blair Eadie

Style Tip: Just because it’s gloomy outside doesn’t mean you have to wear all neutrals!  A pop of color(s) looks so refreshing this time of year BUT must be done right.  Stick to winter fabrications though in these brighter hues to ensure you don’t look ‘out of season’.  A colorful shoe is fabulous too, but again in a winter suede and closed-toe.

Interesting Layering

interesting layering

Photo Credit |

Style Tip: This is a great work look when it’s cold outside, and you need some extra layers!  This is an excellent way to stay warm, without having to match the third piece to your work dress.  Tissue turtlenecks are back in style and look super cool paired under certain dresses.  Lastly, the black suede boots tie together beautifully with the black tissue turtleneck to pull together this outfit.

Sneakers + Denim Jacket

two stylish women

Photo Credit | Accidental Icon

Style Tip: A denim jacket and sneakers are perfectly paired with a dress, especially for a more mild winter day.  I love how her sneakers tie in color-wise with her dress, but also have that gold Nike swoosh to add some interest.  When wearing a denim jacket with a dress keep the jacket more tailored and cropped, and always roll up the sleeves.


Sometimes all you need is a little bit of inspiration to ensure your outfits are always fresh & current! Let these outfit ideas and style tips inspire you to mix and match and experiment in your own closet.


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