From Hot to Cold – Styling a Dress for Winter

It’s no big secret that a long sleeve sweater or turtleneck can take any dress from spring/summer to fall/winter. I see it all the time and have personally done it myself a time (many) or two. What is the secret is understanding the best way to stretch a dress from the warmer months into the colder months.

Today, I am breaking down the different ways to bring a dress from the warm weather and into the winter months based on dress type. Hopefully this will inspire you to dip into your wardrobe and find a way to re-wear your favorite dress.

Before we get started, there are some basics everyone should have in their wardrobe to make the transition from warm weather to cold weather smooth. The basics include:

  • Black, white or grey turtleneck
  • Black, white or grey long-sleeve shirt or sweater
  • Neutral color (black, grey, beige, cream) crew neck sweater
  • Black and Neutral tights

My favorite place to pick up these items is J. Crew or J. Crew factory depending on the current deals and right now with Black Friday there are so many deals! I’ve linked a few of my favorites above.

Shift Dress

Dress (Similar) | Sweater | Booties | Heels

To be totally honest, shift dresses are not my favorite style of dress. I am more of a fit and flair gal myself, more on that to come, but the few I have in my closet are all sleeveless. To transition this dress from spring to winter, I pair it with a black long sleeve sweater or black turtleneck. I really liked how this dress looked with the turtleneck and the unique neckline.

Shirt Dress

Dress | Sweater | Heels | Booties

This shirt dress already came with sleeves which makes it spring and fall ready. To wear it into the winter months I added a sweater on top and tucked it into a belt so that it hit at my waist. Another option is to let it hit at your hips and then it takes on the appearance of a sweater and skirt combo. I tricked my co-workers, they all were complimenting me on my skirt 🙂

Depending on the print of the dress, you can really make it stand out by adding a sweater that picks up one of the colors in the print.

Fit & Flare

Dress (similar) | Sweater | Blouse (similar) | Heels

Ah, the fit and flare dress. This is personally my go-to dress style, I love the way it accentuates the smallest part of my body and hides what I want to hide.

I chose to style this particular fit and flare dress because I wanted to showcase the many ways it can be transitioned into the colder months. Using an accent color from the print (and a personal favorite color for fall and winter), I paired the dress with a sweater on top tucked into a belt to stop it at my waist. Another way a sleeveless fit and flare dress can be styled is by adding a complimentary color blouse or even a crisp white button-down.

Blouse | Dress (similar) | Pink Heels | Navy Heels

Midi Dress

Sweater | Midi Dress | Heels | Booties

When styling a midi dress for winter, it’s important to emphasis the long lines of the dress in tact by using a sweater or long-sleeve shirt to emphasis the natural waist and create the appearance of a skirt and sweater combo. Similar to styling a shirt dress.

Mini Dress

Dress (similar) | Sweater | Heels | Booties (similar)

Last but not least is taking a mini dress from summer to winter. Truthfully, I don’t own many mini dress, not work appropriate and they all seem so short on me but i couldn’t resist styling my new cowl neck sweater with this mini dress to create a cozy but chic outfit. This would be a great outfit to wear to holiday celebration.

Hope you all had a wonderful Thanksgiving and are enjoying your Black Friday. If you’re shopping for yourself, be sure to pick up a few basic pieces to take your dresses from hot to cold!

Happy Styling!

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