My 2020 Style Goals

2020 Style Goals | Millay Blog

While I definitely subscribe to a curated, quality-over-quantity focused wardrobe, I have to confess that this past year has felt challenging clothing-wise. I’d been looking in my closet stumped at what to wear, and feeling I had either “outgrown” some of its contents, or no longer had the lifestyle or career setting where much of it felt handy or made sense.

After all, I’ve transitioned away from the entrepreneur world and now work in a more corporate office;  I’m settling into my thirties so things are starting to fit me differently; and I’ve gone from living in the south to living in New England where winters are not for the faint-of-heart and light layers are not sufficing.

Since my closet currently has a lot of needs, it feels like a good time to reset my style intentions for the year—just like I did for our home—so I can be smart about rebuilding a wardrobe I love, which in turn makes me feel comfortable, confident, and brings me joy!



I figured I can’t be alone in this, so I am breaking down my method for any of you who’d like to join me!


Step 1: Slim Down the Closet

I swing open my closet doors and drawers and ruthlessly go through item-by-item pulling the pieces that I no longer love and divide them into “donate” and “sell” piles. Uncomfortable or too fussy to wear? Bye. Can’t think of the last time I wore it? Not worth the space it’s taking up. You should only be down to the items you LOVE by the end of this exercise – the ones that make you feel great about yourself!

Step 2: Defining My Style

I took a couple hours to go through Lee Vosburgh’s style guide, which I can’t recommend enough. I plan to also go back through it later this year for my Spring/Summer style, and made sure to focus this exercise a bit more on my cold-weather style for now. By the end of her guide, you’ll have identified what items you love that you already own and why, what you are drawn to, what you hate, and a precise identification of your style and color palette!

Step 3: Articulate Priority Purchases

What important gaps does my closet have and what statement items do I want to add for a little more personality? For me, I lacked a heavy duty winter coat, and pragmatic but stylish sweaters for work.

Statement items I’d love to also keep on my radar to add to my wardrobe this year are the perfect leather jacket (I have my eye on this one) and an oversized neutral blazer that can be dressed up and dressed down.

Step 4: Determine a Purchase Plan

Looking at the list of what I need while also keeping an eye on my budget, I created the following golden purchase rules for myself:

  • Purchase only one item a month (got this idea from Tess Montgomery’s #oneitemamonth 2020 post): this will really slow down what I purchase and why. (Not to mention feel less guilt when I splurge on an item, since I’ll likely be able to better afford the splurge!)
  • If I purchase anything in addition to the one item, I’ll have to sell or donate an existing item from my wardrobe.

Important Truths to Remember

  • This is not about adhering to rigid rules but rather about creating guidelines for a more thoughtful closet and becoming more disciplined in purchasing habits. I may stray a little here and there (and that’s okay!), but having these as touch-points to come back to is a great starting point.
  • Keep items I love bookmarked, and revisit them over time to see how much I still want them down the road. You’d be surprised how much more you might prefer something else over time or that you’ve lost interest in something (so good thing you didn’t end up buying it right away!)
  • Don’t fall victim to FOMO pressure…if it sells out before I can afford it or before you can decide whether to even purchase it, all is not lost! If you search around enough, you ought to be able to find it on Poshmark, The Real Real, Vestaire Collective, or Ebay. So take your time deciding. And if I can’t find it? Maybe it just wasn’t meant to be.



I’m also extending this more thoughtful approach to “my shop” for both myself and for you all. I went through and intensely cut down what I link to, so that it is truly a super curated offering of considered items I either own, love, and highly recommend, or have on my own wishlist!




you can explore more of the everyday essentials that i swear by and

my personal style selects over in the full shop



What are your style goals for the year? Have you ever done Lee’s Style Guide? I love how precise it was in getting me to articulate my needs, how I actually live, and what things I love and don’t love within my own closet and why. She has a lot of other great resources too, definitely worth digging around her wonderful site!




main photo by Justin Coit / second photo

Join the conversation and share your thoughts!

  1. […] goals for the year and set out a concrete plan to execute them. Mary shared her findings in this Style Goals blog post, which is certainly worth a read. Thanks […]

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