Style + How To Wear It

Re-Starting a Professional Wardrobe for a Post-COVID Transition

When I went back to the office in January, I had a problem.  My pre-COVID professional wardrobe was made for someone ten pounds lighter with hips 3″ smaller.  Every skirt was uncomfortably snug, every jacket had to be worn open, some blouses were unwearable.  It was a misery.

While I’m eating better and working out more, I have a ways to go before I can wear the bulk of my wardrobe comfortably again.  And judging by some of the questions sent into my e-mail and DMs over the past few weeks, many of you are facing a similar struggle as you confront returning to the office and your professional attire.

Dressing through this awkward transition phase has been tough.  I’ve had to figure out what I need to get through and replace a few staples with temporary counterparts.  Luckily, professional attire is deeply discounted right now, so I can wear these pieces now and Poshmark them later without guilt.  So I thought I would create a guide that you can reference when you head back to the office.

Where to begin?  Go to your closet and put together five professional outfits using your favorite, staple pieces.  Now try them on.  This may sting a little, but you need to know what fits and what doesn’t.

Do they zip or button?  Can you lift your arms?  How does it feel when you sit?  Really give them a good test run.

Make a List. Now, write down which pieces you may want to buy in a larger size to fill your transition wardrobe.  These pieces will be unique to you.  For some it will be new jeans.  For others it will be new business suits.

Set Aside the Budget. I gave myself $500 to buy some replacement items and $750 to pick up a few new pieces that I can tailor down a size later.  Tailor your budget to your needs.  I’m hitting great sales and working Poshmark, so I won’t need my full amount, but I wanted to set aside enough money so I would feel good about what I was buying and not be draped head to toe in Forever21.

Choose Styles That Are Affordable to Tailor.  A good tailor can rescue anything.  (My wedding dress tailor turned a size 12 Oscar de la Renta gown into a size 6.)  But some things are cheaper and easier to tailor than others.  Pencil skirts, sheath dresses, and simple blouses are simple to alter.  Pants and blazers can be tailored, but cost more.

Stick to a Color Palette.  My work wardrobe right now is mostly black and white with some navy thrown in.  Keeping to a neutral, monochromatic palette makes buying new pieces easier because everything will go together.  It also makes the process of getting dressed in the morning a cinch.

Now that we’ve covered the basics of deciding what goes in your transition wardrobe and what it should cost, let’s talk about the pieces that I purchased.

Hue Blackout Tights // One of the darker moments of my return to the office was the morning that I put on my tights, and realized that they were too tight.  Uncomfortably, sausage-casing tight.  It was time to go up a size.  These Hue Blackout Tights were my favorite <$20 pair.  They are very black, which I love.  They also have no control top, which makes life more comfortable.

If you want a better pair of black tights, Falke are my favorite upgraded tight.  They wear like iron, so you won’t need to dispose of them frequently.  Though I recommend getting a garment bag and washing them on delicate to prolong their life.

Ann Taylor Pencil Skirt // This was the piece that absolutely had to be replaced, no exceptions.  So I bought my favorite Ann Taylor Ponte Skirt and my Ann Taylor Seasonless Stretch Skirt (also in petite) in the bigger size.  I wear these multiple times over a two week period, and I needed larger ones.  The great thing about these skirts is that I can easily have them tailored down if I want, or I can donate them to Dress for Success.

Rag & Bone White Blazer // I thought my white blazer fit.  Then I tried to wear a blouse under it and lift my arms… Nope, didn’t actually fit.  Luckily, one of our interns could benefit from my loss.

Replacing my white blazer was tougher than I thought it would be.  I chose this Rag & Bone blazer (on deep discount) because it had a simple cut and a one-button style.  If you need something under-$100, this NYDJ collarless blazer and this white blazer with a ruched sleeve are both worth a look.

DvF Aleka Tie Neck Dress // I needed a black dress with a bit of color to wear under a black blazer.  These dresses make my life comfortable and easy because I love wearing dresses.  I chose the Aleka Tie Dress, but I also picked up a couple of patterned wrap dresses on Poshmark.

Finding dresses that blend black and white or are black and a color helps me wear all black without looking like I’m on my way to a funeral.  You can see one of my dress under blazer outfits under ‘My Outfits’ on Instagram.

Ann Taylor Wide Leg Pants // You know my feelings on pants, I don’t wear them.  Until I found these wide leg pants.  I love them.  Love.

The wide leg is comfortable.  The high-waist keeps shirts tucked in.  And they look very dressy, which I enjoy. They’re back in stock in a handful of sizes (also in petite).

So these are the five items that I couldn’t live without.  What your must-haves be?

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  1. Crystal says:

    Thank you for the tips (although I don’t imagine I will need to revisit my work wardrobe until at least close to 2022).

    I haven’t purchased a DVF dress in a while. Do you have recommendations on sizing as compared to other brands we might own (like MM LaFleur or Ann Taylor) or any suggestions on reasons to size up/down (like if they run narrow through the bust, arms, or hips)? Thanks!

    February 23, 2021/Reply
    • Belle says:

      I usually go up one size in DvF

      February 23, 2021/Reply
  2. Kate says:

    This post is so helpful. I’m about to embark on a purge of my pre-baby work wardrobe (I weigh less than ever but nothing fits the same) and this will be my guide!

    February 23, 2021/Reply
    • Sarah says:

      Me too. Weirdly even though I’ve lost a lot of the baby weight, nothing really fits right. It’s like I have a whole new, strange, kind of lumpy? body. But I could use this as a fun excuse to shop with these great guidelines.

      February 24, 2021/Reply
  3. cait says:

    I love this feature since it speaks almost EXACTLY to my experience!
    I went back to the office in January on a 50% wfh schedule. I had a similar rude awakening but my weight gain has been greater, which means the only things that fit were either oversized pieces or things that had stretched. It also means that some of the silhouettes I used to rely on aren’t as flattering anymore.
    I’ve never found pencil skirts comfortable, so I used this as an excuse to be done with them once and for all. For bottoms, I bought 2 a-line skirts in pretty colors, a pair of black jeans, and a pair of dark blue jeans. For tops, I bought the white JCrew classic blouse you recommended, a colorful patterned blouse, and 2 solid drapey blouses from the Lush brand at NordstromRack.
    My office is business casual, so I mostly have knit blazers or cardigans. A few blazers have been relegated to “sleeveless top only” status, but most of the cardigans still fit.
    Since I only go to the office 3 days a week, this should get me through for a while!
    I think that I will need to get some new undergarments that better fit my new size as well. Do you have any tips for figuring out a new bra size under our current collective circumstances?

    February 23, 2021/Reply
    • sara says:

      your line about silhouettes no longer being flattering is 100% me as well! suddenly my go-to outfits just look sloppy now.


      February 23, 2021/Reply
  4. Char says:

    Goodness thank you for this post – discovering that most of my clothes no longer fit has been brutal on top of everything else we’ve been through. I have the option to come back into the office and I dread the day when I need to move past just sweaters and jeans and wear a real skirt/dress/blazer. Now to figure out how I’m going to fit into a bridesmaid dress in June….

    February 23, 2021/Reply
  5. Monica T says:

    I recently purged my closet of all the pandemic sale items that were “too good to pass up” but that don’t pass my basic lifestyle and preference litmus test. Call this a pandemic fail, but it felt good to get my closet back to “me”. I’ve been adding back in basic t-shirts in a size that is comfortable (a size bigger than last year), and replacing my stretchy jeans because after a year of continuous wear and several previous years of weekend wear, they are getting holes in the crotch area. Like some others, I’m going to be home probably for most of 2021, if not all, so stretchy jeans and tee’s are perfect refreshes for WFH life and the upcoming season change.

    I too have restarted my strength regimen mostly to stave off the back pain I was experiencing chronically since WFH started but never before. I want to rebuild my muscle but this inevitably leads to a size decrease, but one thing I’ve learned in the pandemic is I like loose comfortable clothes, and I won’t be rushing back to super fitted tees any time soon.

    February 23, 2021/Reply
  6. Lost says:

    Thank you for this! I know I’ll return to the office, at least a few days a week, at some point this year. I’ve worn only elastic waist pants for a year now and am really struggling with the thought of wearing real work clothes again.

    February 23, 2021/Reply
  7. AJT says:

    This is a really helpful starting point! Thank you!

    I wanted to make a plug for ThredUp too – you can filter for items by “new with tags” if you don’t love used clothing – but it’s much friendlier on your wallet (and the world) to buy used things to help fill some closet holes. I got several professional maternity things there pre-COVID, and some comfy wfh items during COVID. I was having a hard time justifying buying brand new items I knew I would only wear for a few months, but clothes that actually fit correctly make a difference!!

    February 23, 2021/Reply
    • Emma says:

      I also love ThredUP! I’ve gotten some amazing quality, new with tags, basic pieces for super low prices.

      February 23, 2021/Reply
  8. Diane says:

    I bought the Rag & Bone blazer in pink when you recommended it last summer and I absolutely love it. I am tempted to jump on the white version too, but struggling justifying having another white blazer! I highly recommend it.

    February 23, 2021/Reply
  9. Emma says:

    I’m still WFH full-time and anticipate my position converting to 50% WFH indefinitely. I’m down to a uniform now. I have two pairs J. Crew vintage straight jeans (one dark, one light wash) that I have forced myself to wear on work days or when leaving the house. It helped me minimize the COVID weight gain. My choice in tops is a black or white v-neck t shirt. I alternate between a barefoot cardigan and a grey athletic hoodie. Everything looks good together and not a lot of choice fatigue. On weekends I wear leggings but everything else is the same! I’m also replacing items as they wear out with brands that make clothes to be washed less. My favorites so far are WoolX, Ably, unbound merino, and minus33. I can’t wait to figure out what my summer uniform will be! Probably cutoffs with the same t shirts, a full skirt, and a few maxi dresses.

    February 23, 2021/Reply
  10. Karen Carr says:

    What shoes does one wear with wide leg pants? I’m also having issues remembering how to wear flares but I do know anything with a pointed toe works best. Would love a post on which shoes to wear with different types of pants. Many thanks!!

    February 23, 2021/Reply
    • sara says:

      square or pointed booties have been my go-to with wide/straight leg denim!

      February 24, 2021/Reply
  11. Rachel says:

    Def hit up those thrift stores too. I’ve been finding killer deals on clothes from people who also found they’d added the quarantine 15, so I am using those clothes as my tide-over until I am able to get back to the active part of my job.

    February 24, 2021/Reply