How to Build A Transition Wardrobe

Tracy writes in:

I need to assemble a “transition” wardrobe. I’ve recently lost 25 lbs. and nothing I have fits. This is a good problem! However, I still have 50 more pounds to lose so I don’t want to invest a lot in clothing just yet. Any advice on what pieces to buy that would be affordable and allow for mixing & matching? I’m tired of dressing like a fat, frumpy housewife! I am a stay at home mom though so I need comfortable, casual clothing most days. Any advice you can give would be greatly appreciated!

First of all, CONGRATS!!! That is a great accomplishment. You must feel great.

On the other hand, there is nothing worse than looking into your closet in the morning and feeling like you have nothing that fits. And I know that of which I speak.

I birthed 3 children and I gained 45 lbs with each pregnancy. On my 130-lb frame, that was, um, quite a lot.

Yes, I just disclosed what I weigh. I’ve broken the cardinal rule. Now we may as well go ahead and discuss politics and religion. Who wants to start?

Oh nevermind, let’s stick with fashion. It’s so much more fun.

Here are my best tips for building a transition wardrobe while you’re losing weight:

Buy Your Size

It is my humble opinion that you need to have a few essential pieces of clothing that fit, no matter what your size. If you are losing weight, or  even *gasp* gaining weight, you will feel SO much better and SO much more motivated to eat well and exercise if you feel good in your clothes. Everyone woman should have one basic wardrobe item that she loves and feels good in.

If you are a stay at home mom, make sure you have a pair of well-fitting jeans in your closet at all times. If you work in an office setting, maybe your basic wardrobe item should be black slacks or a pencil skirt. But you need a basic item of clothing that you can pair with lots of different tops so you don’t look like you’re wearing the same thing every day.

I always made sure I had a pair of jeans in my size when I was losing baby weight. There were times when I had jeans in about 5 sizes in my closet!

At the same time, you don’t want to go all out and buy designer jeans that you’ll only wear for a month, so definitely shop the lower priced stores. You can usually get something current and not too spendy at Kohls or Old Navy.

Like these Rockstar Bootcut Jeans at Old Navy are just $19.99.

I realize not everyone can afford to have three different sized wardrobes in their closet, but I felt SO much better about myself when I was “downsizing” if I had a few things that fit well – at least one pair of jeans, a few tops, and a Sunday outfit. You can change it up with accessories that fit no matter what your size — shoes, handbags, jewelry, scarves.


Even in the summertime, you can wear light layers. But going into fall, the weather is perfect for layering. A thin cardigan can cover lumps and bumps and is flattering when worn open — it creates a column effect down the front that is elongating and slimming.

image via Old Navy


Slimmer jeans with a looser top will often help you feel thinner, and loose ruffley tops can help disguise a thicker midsection.

images from Old Navy

Try adding a scarf or a statement necklace to draw the eye upwards, away from problem areas.

Or sometimes, on the right person, a shirt with the banded waistline, another hot trend this season, can help the tummy issue. It isn’t too figure hugging where there might be some extra stuffing, but instead of being too flowy all the way down over the hips, the hem of the blouse sits right on the hips and brings it back into the body. It’s important not to wear this style too big, though, or the blousy part will balloon out and make you appear bigger than you are.

images from Old Navy


A jacket or dress with structure is always a good idea! Remember how Stacy and Clinton used to always say, Lock and Load!?

images via LOFT.com

Key Pieces to Have

These are the key pieces I would try to have at all times in your current size:

  1. a pair of pants — jeans or dark slacks, depending on your lifestyle — that you can wear almost every day and mix and match with different tops for different looks
  2. cardigan or fitted blazer — find one in a neutral color that allows you to layer different tops under it. A cardigan will transition with you across several sizes, so you won’t have to keep buying this piece over and over. A fitted blazer DOES need to fit, so take this into account. if you’re a professional, it may be worth the investment. for a stay at home mom, either go for a cheap one or wait until you’re at a size where you plan to stay for a while.
  3. several tops that you can mix and match with your jeans/pants and cardigan
  4. accessories don’t come in sizes, so invest in some great jewelry, scarves, shoes, etc that will work no matter what size you’re wearing

The key, as always, is fit and proportion. No matter what size you are, make sure you have a couple of basic pieces you feel good in.

Good luck on your weight loss journey!!!!!

For more  fashion for women over 40, sign up to  receive my fashion & beauty digest  in your email inbox for a weekly recap of my fashion and beauty posts!

Join The Conversation

9 Responses

  1. I lost over 100 pounds, it took about 1.5 years. Thru the process Thrift Stores were the way to go for me. I was able to get several pieces that didn’t break the bank and transition thru the entire process feeling stylish.

    1. Yes, thrift stores are awesome for this if you have the patience. 🙂 I never did, so I relied on places like Old Navy and Kohl’s. But thrifting is a great way to fill in your wardrobe while you’re down-sizing.

  2. I also have lost a ton of weight.. over 100 lbs.. and feel great… and fabulous!!!
    Buying new things is alot of fun.. for awhile.. then it just gets expensive and sad
    when those things no longer fit… Christopher and Banks was a life saver for me, their
    sales and clearance prices are amazing.. I tried to buy basic colors in slacks and capris
    on the off season, $6.99..free shipping as a rewards member. Then I always had things
    to slim down into. I try to consign things when I can no longer wear them. Now I only buy things I LOVE!!! I have a completely new wardrobe of small size clothes (small shoe size too!) I love it!!

  3. I too, joined the weight loss club over the last year. It’s a fabulous feeling and so much fun to feel good in clothes again.
    I would like to suggest shopping consignment and consigning. I find that shopping consignment stores gives me access to higher end brands with better fits and cuts but at a price within my budget. Also, by consigning my old, too big clothes, I had money ready to spend when I was in a new size. A winner on both accounts in my book!

Leave a Reply

Your email address will not be published. Required fields are marked *

Close this search box.