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Get Ready for our 2020 Wardrobe Challenge!

Get Ready for our 2020 Wardrobe Challenge!

Today, I’m wrapping up my work year. 

I can’t wait to unplug for a few days and turn my attention to my family. But once Christmas is over, I’m also looking forward to a few quiet days in the office to start rolling our the first phase of our 2020 initiative – focused on helping you build a classic, modern wardrobe. 

But I could use your help! 

Every piece of content I put out is based on a question, or comment that you share here, on Instagram, or in our Facebook group. 

How to Build a Classic Wardrobe

I would love to hear from you so I can keep moving in the right direction. 

In the comments below, share with me any frustration you have when you are shopping, or trying to build a wardrobe. 

Do you shop in stores, or online?

What are your go-to stores?

And, where have you been successful? 

Anything you’d like to share will be a helpful in making sure our 2020 content is helpful for your everyday life. 

Free Wardrobe Checklist

FREE Printable Wardrobe Essentials Checklist

If you haven’t already, download our Free Wardrobe Checklist so you have it on hand for our upcoming Wardrobe Challenge in January! 

Our Wardrobe Challenge starts on Friday, January 10th. 

Wardrobe Challenge

I have been hosting some kind of Wardrobe Challenge for four years now. With each new year, I tweak it and build on what we did in the past. 

This year will be no different. 

To start, we’ll edit our wardrobes over a four week period. And, like every year, I’m doing this with you! We’ll be ruthless, and strategic. Plus, I’ve discovered some fantastic organizing tools that will transform any space!

Each challenge will be posted here, on The Well Dressed Life, every Friday starting on January 10th, with the last edit challenge going live on January 31st. 

Where I’m changing things up is after our month of purging, editing, and defining our style, I’m going to work with you as a virtual stylist.

Every Friday in February I’ll post a style challenge. Maybe it’s wearing a piece you haven’t worn in a while, dressing up jeans for work, or incorporating a trendy accessory. 

I’ll use IGTV (Instagram) and Facebook Lives to speak directly with you, answer your questions and give you advice and feedback. 

More details will be announced right after the holidays. For now, be sure to download our wardrobe checklist, follow along on Instagram and join our Private Facebook group

I’m taking tomorrow “off” so I can finish getting ready for Christmas and organize Vivi’s first birthday party. But I’ll be back on Monday sharing some highlights of the year, and launching our Best of 2019 Week that will run from Tuesday until January 2nd. 




Get Ready for our 2020 Wardrobe Challenge!

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Wednesday 25th of December 2019

We are the same age! I would love to see more options for working professionals. I am an attorney and my go to is a sheath dress with a black jacket and black boots if I am not in court. I am bored wearing black jackets all the time. Blue jackets are hard to match other blues/ dresses. And then what do I do about shoes? I am basically looking for a non-black uniform. Please help! I really like mmlafleur and The Reset and Nordstroms. None of the items have to be from these brands. I just need inspiration for getting dressed in the morning. I am a West Coast gal. Thank you!


Sunday 22nd of December 2019

I am excited for this challenge! I am 26 and typically only shop online (unless my mom has asked me to go shopping with her for fun!). I get overwhelmed easily in stores and get exhausted when I'm frustrated by not finding things that I love. I never want excess or too many things that don't match everything else in my closet. Shopping online helps me bc I can sort by color and have a list of the basics that I need. That way I search specifically for those items and not get distracted by everything in the stores! I can't wait to see your organized approach to the wardrobe challenge bc I truly am a lost cause. I just go for what's easy and don't spend the time to look put-together.

Denise Fairchild

Saturday 21st of December 2019

I very much appreciate your style! I am recently retired and went from dress pants, blazers and skirts to the unknown. I also have recently moved to the northwest. I resist the “uniform” that I see of the turtleneck with the puffer vest or the athleisure (dumbed down) version of dressing. I’m sorry if that offends anyone, but I was raised in the east coast and the understanding was that you always dressed your best for the situation. Help! I’m struggling.


Saturday 21st of December 2019

Loft, Nordstrom, banana republic and Athleta


Saturday 21st of December 2019

I probably shop 50/50 on line vs stores. Because I live in Canada it's better to shop in store for J. Crew and Ann Taylor. Online is Gap, Banana Republic and Old Navy.

Sizing drives me a bit crazy especially with Old Navy as there isn't any consistency. I seem to be a consistent size for J. Crew and Ann Taylor but my issue is I'm 5'6" and thin with long arms and legs so lots of sleeves and pants are too short for me. I get inspiration from blogs but need to make sure they are age appropriate (I'm in my mid 40's) and reasonably priced. I tend to gravitate to neutral colours (black, white, grey, navy). I've been trying to focus on pieces that I can wear as multiple outfits.

I've recently transitioned to working from home. I have a closet full of business casual clothes that I don't wear very often anymore. I still need to keep them for times when I do go into the office, but now I tend to buy more casual attire. That said, I don't want to look to casual - I need to be appropriate for video calls.

I'd love to see ideas on how to accessorize as I have lots of necklaces and earrings that just hang in my closet and never get used.

Looking forward to seeing all you do in 2020. Best Wishes!

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