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11 Winter Dress Outfit Ideas

(Plus 9 pant options including winter outfits with white jeans)

Whether you’re going to work, going out with friends or running errands, the key to winter dressing?

Here are the biggest fashion tips how to look stylish in the winter. (Especially if you’re wearing dresses).

1. Layers

Layers (like blazers, vests etc) are one of the easiest ways how to improve your style and how to be stylish in the winter.  If you run cold, you can add thermal layers.

Most of these outfits include, almost always, second hand or resale pieces.

Why buy second hand?  I teach this inside of Stylist in Your Back Pocket during the shopping module but it’s such a great win-win for our planet and wallets.  The bigger bonus?  Unique pieces that are YOUR unique personal style. (Unsure of your personal style? This is also a module inside of SIYBP!)

2. Best Stylish Waterproof Boots 

All of these dress outfits would be worn with tights and the best stylish winter boots waterproof.  And, not to worry, for those of you that commute, I’ve included my best waterproof walking boots.  If you notice the pant outfit options at the end of this blog, I am wearing my all-time favorite winter boot by La Canadienne.  An investment for sure but if you experience winters like we do, these are way worth it.

And, you’ll notice I am not alone. There are over 2,000 reviews on Zappos for these beauties.

They also look great with dresses (see coat and blue romper photo). So they absolutely check the versatility boxes in my (hypothetical) style book.

 I receive a Starbucks Pike Roast-like commission from these links below if you purchase using my link.  With that said, I only recommend brands that are my very favorite tried-and-true. And NO this is not a sponsored post (yet).

La Canadienne are my go-to winter and fall stylish weatherproof winter boots.  I would be a sales rep for these boots if I could because I am truly obsessed with the quality, comfort and waterproof-ness! Plus, these are the best winter boots to wear with dress pants.

3. How to style winter boots 

As a personal shopper stylist in Chicago, I will always choose comfortable and stylish options. You do not need to sacrifice your style for comfort (ever!)

There are so many incredibly stylish comfortable winter boot options available and I’ve included many in my shopping round up for you here. 

There’s a few way to style winter boots:

  1. Pair them with a similar color tight for the ultimate chic look that elongates your legs
  2. Pair your short ankle ones and have a chunky sock peek out like these cute rainbow ones here. 
  3. Wear a similar color shade boot to the closet shade of pant
    white jeans | tan boots
    dark denim | black boots

*Tried-and-true favorites. Warm and beyond comfortable!


HOW TO DRESS STYLISH FOR THE WINTER WITH WINTER STYLE DRESSES

  • Earrings: Baublebar second hand | resale
  • Blue dress: Yumi Kim
  • Oversized sweater: Kickin’
  • Coat: Soia and Kyo via Cinnamon Boutique
  • Boots: La Canadienne

  • Blue dress: Rebecca Taylor via Cinnamon Boutique
  • Cream turtleneck: gifted (Thanks Julie!)

  • Dress: H&M
  • Coat: Amiyu second hand | resale
  • Sweater: Club Monaco second hand | resale
  • Scarf: Alex & Grey (I have a few for clients, message me if you want to purchase!)
  • Earrings: Rumination Studio

  • Earrings: Grandma’s
  • Turtleneck: Theory and then RIT dyed tie-dye
  • Belt: Grandma’s
  • Dress: Anthropologie

  • Blazer: Maje second hand | resale
  • Dress: Joie via Eco Chic Boutique
  • NecklaceRuby in the Skies

  • Crop leather jacket: Antonio Melani second hand | resale
  • Dress: Joie via Eco Chic Boutique
  • Grandma earrings 

p.s- this would also be cute with a puffer vest underneath if it fit!  


  • Dress:  MSGM via Poshmark
  • Puffer vest: J Crew via Thredup
  • Coat:  Isabel de Pedro via The Girlfriend Sale
  • Earrings: Grandma’s

  • Jacket: Kid’s Zara second hand | resale
  • Turtleneck: Target? 5+ years old?
  • Dress: MSGM via Poshmark
  • Earrings: Grandma’s

  • Blue dress: Rebecca Taylor via Cinnamon Boutique
  • TurtleneckCinnamon Boutique  (4+ years old)
  • Earrings: Baublebar second hand | resale
  • Belt: Bottega Veneta via Grandma Jean
  • Vest: Rag & Bone

  • Jacket: Zara kids via second hand
  • Dress: Joie via Eco Chic boutique
  • Belt: Bottega Veneta via grandma’s
  • Cashmere turtleneck: Cinnamon Boutique

  • Dress: MSGM via Poshmark
  • Blazer: Michael Kors via second hand | resale
  • Earrings: Grandma’s

Dresses not your thing? No worries, I’ve included a few pant outfit ideas for you as well.

If you’re stumped how to wear white jeans in the winter I’ve included some ideas below.  This is when I wear my La Canadienne taupe / tan boots.  (I have a knee-high pair for dresses) and a short ankle pair for jeans).

This is also an easy how to wear cropped pants in the winter trick.  And yes, you can wear crop pants if you’re petite or short (I am 5’3).   I love crop pants because of their versatility aka you can wear the all year long.

With boots during the winters or sandals in the summertime, they look equally stylish worn both ways.

I’ve included a few tan pairs in the shopping at the very top of this post.   If these are way out of your price point, don’t forget you can always look to buy these second hand.  Shoes are typically hardest to find second hand because the sizing can be tricky for some folks but once you know you’re size, this helps you shop easily second hand.

If you want to learn to shop smarter, remember this is a module I teach inside of Stylist in Your Back Pocket. 

MAKE SURE TO SAVE THIS POST, PIN THESE OUTFITS OR HOP ON MY NEWSLETTER FOR EVEN MORE STYLISH OUTFIT IDEAS AND TIPS!

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