What to Wear During a Transition Period


Thanks a lot, you guys. Because of you, and because of your warmth and candor and all-around awesomeness, I have decided to completely scrap my editorial calendar for 2016 and start over. Because, frankly, your ideas are better than mine. In the next few posts, you will find specific answers to the problems you shared with me in your survey results, from how to artfully conceal a mummy tummy to how to dress for your age without appearing too old, too young, or just too, well, anything. The first topic is one that comes up again and again, and most of us have experienced it. What to wear during a transitional period. Transitions are tough because we often suddenly find that what has worked for us all along is no longer working, and we are forced to reinvent ourselves, for a time, or possibly forever. Here’s what you told me you struggle with during those tricky transitions…”

“Finding my fashion “groove” back after baby. Dealing with fluctuations in weight/body size; updating my wardrobe with cute additions that are a) not 5+ years old, b) not too expensive c) flatter my slightly-still-pregnant-looking belly, d) are stay-at-home friendly, and e) still look fashionable!”

“Trying to lose weight right now and need some advice on what to wear while I am transitioning to goal weight.”

“I am currently working on losing weight. Need help in figuring out what [are the] best outfits for me. Casual and dressy.”

“I’m a 68 y/o woman who is presently about 100 lbs over-weight. My younger, thinner me is in there, wanting to desperately get out, but until I can get some of it off, it’s hard for me to feel comfortable in old, fat lady clothes. And that’s all I can find in the stores in my size, anyway.”

“After being diagnosed with a chronic illness, I was put on several meds that made me gain over 40 pounds. No matter how hard I try I can’t lose it. It’s time to have a “real wardrobe in this bigger size. I don’t know what to buy that looks good and hides my trouble spots. I’ve always gravitated to the same cuts and styles that looked good on me then…  They don’t work any more!”

“I’m a new mom and I am about 10 pounds lighter than pre pregnancy. All of my clothes look frumpy on me and I feel jeans are very uncomfortable right now because of csection and spending most of my time on the floor with my one year old.”

And these are just a few of the survey responses about this topic. It has also come up a number of times in BeautyMommy VIP.

“I’m spring cleaning my closet and I have run into a conundrum. I have been losing weight and have clothes in my closet from size 6 to size 12. Right now, I’m a size 10/12, and I’ve been trying to only keep the clothes I love, but some of the clothes in my current size I don’t really love or like very much, but it’s what fits right now. What do you suggest I do?”

Here, my step by step guide to transitioning your wardrobe.

1. Decide if it’s a short or long term transition.

A long term transition, like deciding to stay at home after years of working outside the home, retiring, or returning to the workplace, all demand a long-term solution as you gradually shift your wardrobe away from pieces that defined your former lifestyle and into something that works for your new life. Even though pregnancy seems like a defined, shorter term transition, anyone who has ever had a child knows that the wardrobe demands of pregnancy/new motherhood last long after the baby weight is off.

2. Assess What You Have

As I said to the VIP member whose clothes ranged from a 6 to a 12: “When your wardrobe is limited because you are only wearing a part of it and are in a transition period, then you are essentially working with a capsule wardrobe and you can treat it the same way. So take all of those pieces in your current size out and create as many combinations as you can with them. Keep a running list of any basics that you are you are missing. If you are really missing a black tank or a pair of jeans, for example, for just a small investment you can have a couple of those pieces that will fill in the blanks in your wardrobe.” So start with what you have, and use that as the foundation of the new capsule wardrobe that will carry you through this season of life. And then, just for now, take everything else out of your closet, if at all possible. Stick them in an old suitcase, or in a spare closet, or in a bin, but get them out of there.

Another VIP member had this advice: “I am in the exact same position!! Literally!!! I just did this. I’m between a 10/12, still closer to 12. I got rid of anything that was a size 6. Then I weeded down the size 8 to just the stuff that I really really liked and could still picture me wearing all the time. Then with the size 10 I got rid of anything I didn’t like and kept the rest. And I kept all the size 12 except something that I really hated. Cause I need to keep as much of that size as I can to make outfits. Even if it wasn’t my favorite; it kept me from having to buy something new. Because my theory is… once I lose a little weight I’m going to reward myself with a few new pieces to go with the size 10. Then when I get down to an 8 I’m going to reward myself even more with like 1/2 a new wardrobe. And if I get down to a 6 again…well then I deserve a whole new wardrobe!!!!! I then packed away all the size 8 so they weren’t taking up space. And I ended up getting rid of 4 of the huge Rubbermaid containers of clothes. And I feel better all the way around for all the hard work.”

3. Create Outfits

See how many combinations you can create with what’s left in your closet. How much mileage can you get from the remaining 10 pieces, or 20, or 30. Make as many possible outfit combinations as possible, and snap quick pictures of them on your phone for easy reference. As you do this, you’ll start to notice gaps that are missing, pieces that will tie the rest of your wardrobe together. These are generally the basic pieces that I recommend as the foundation for most wardrobes, and what I call the “core” capsule wardrobe. They’re not exciting on their own, but you will get a lot of mileage from them.

4. Shop for the Rest

The easiest and least expensive way to do this, in my opinion, is to shop online. Check sites like Everlane for well-priced basics, or look for sales at favorite stores like J. Crew, Loft, and Nordstrom. If this transition is truly short term, start with the basics only and integrate them into the pieces that you already have. For the rest, consider wardrobe rental services like Gwynnie Bee and Rent the Runway Unlimited. (More on these in an upcoming post). Live with this pared down capsule wardrobe for as long as you can, and save the additional shopping for when you have a sense of what you really need.

5. Splurge on Accessories

If your capsule wardrobe of mix and match pieces feels a little drab, go crazy with the cutest accessories you can find. After all, a necklace works for you at any size, and so will shoes, scarves, and bags. You can bring a wardrobe of basics to life this way! They offer a great way to inject color and personality into your outfits.

Wondering what a sample capsule or transitional wardrobe looks like? Check out the one below, which I created for a BeautyMommy VIP member with a casual lifestyle and a love for denim.


Capsule Wardrobe Style Dial 2 Classic


Miss Selfridge denim dress

LOFT red top

J Crew white lace top

Topshop flower shirt
$24 – nordstrom.com

J Crew t shirt
$42 – jcrew.com

NYDJ 3 4 length sleeve top

J Crew racer back tank top

Blue blouse

Asymmetrical jacket

White House Black Market ankle jeans

CJ by Cookie Johnson jeans
$90 – neimanmarcus.com

Miss Selfridge mini skirt

JustFab jeans

Old Navy open toe mule

TOMS flat

For more ideas on creating a capsule wardrobe, read this post. And while this may be an oversimplification of the process of transitioning your wardrobe, it’s a great place to start the process. Next week, I will be going into more detail on the specific challenges described above, from shopping for a changed body to finding clothes that fit your lifestyle and your budget. Until then, keep those survey responses coming!


  1. Martha Brinkmann says

    Thank you for deciding to address the common needs of women whether we are 19 or 79 (my age). I find that the needs are similar in leaving college to entering the work force. Or from there to pregnancy, to being a stay-at-home mom. And then reentering the working force while still balancing all those past lives. Now I have finished most of those other lives — still learning, but not in school, no longer the young professionals, or the young bride trying to build a home, follow by 4 pregnancies in 6 years, motherhood, raising four teenagers while trying to develop a new career, working 50 plus hours a week
    Struggling with husband’s retirement due to illness while he becomes Mr. Mom and not being able to find the flour or sugar anymore as your work becomes more more demanding. Children grow up and are out of the house, grandchildren arrive…finally retirement. Volunteering. Aging. Looking for meaning in life … Each of these transitions have certain demands for health, age appropriate wardrobes and make-up while staying beautiful, charming, vital, staying current, continued learning, loving, caring all the while hopefully staying happy, content and pleasing God and staying within his loving arms while continuing to serve him. So helping young moms is very important because there are so many changes. Showing women to adjust to changes…knowing…that everything will workout and with some small efforts there are many wonderful times in life still ahead. So you have a great future and occupation ahead …to provide loving and helping women to be joyful and how to look and feel their best.
    Sorry to write so much but I am sure you are sensitive person. Since I believe you are young, you will be especially good at this.

  2. says

    Martha I can’t tell you how much this means to me!!! It really made my day. Thank you so much for that perspective and wisdom. Sometimes as moms of young children we have to stop and remind ourselves that we are in one of the best but busiest seasons in life and to pace ourselves and to go easy on ourselves sometimes. There are just sooo many demands. Your insight is so valuable and I hope it will help many. And thank you for the encouragement! I hope that the women who read my blog will know how passionately I feel about this. I truly believe every woman and every mom should feel and look her best every day and to set that example for their daughters and nieces… Thanks again! (Also, I am in my 40s, so not that young, but I will take that as a compliment any day! Thank you!!)

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