10 Tips for Dressing Yourself During Your Weight Loss

“What should I wear?”  It’s a classic dilemma that sitcoms have used to poke fun at people,  mostly women, for ages.  But when you are an eventually former fatty, (or for the layman: when you are losing weight) that question becomes incredibly difficult to answer.

So how do you go about dressing yourself while losing weight? If you have stacks of excess money, each new size can be a fun shopping opportunity.  (And while you are out spending those stacks of excess money, feel free to sponsor a worthwhile website like EventuallyFormerFatty.com!)  But if you are on a budget, or are not comfortable spending at every size, it can be daunting to know what to buy as your size fluctuates.

Have no fear!  I’ve got tips for you to succeed! Your weight loss wardrobe awaits!

1. Buy clothes on the cheap

How to dress yourself while losing weight

This sounds like a no-brainer, but sometimes you forget the deals and steals you can get if you look hard enough.  I practically live at my local thrift shops, hunting the racks for treasures.  Shop the thrift shops around holidays too!  My local Savers has sales pretty much every holiday, which means I can get their already-inexpensive clothes at prices that border on the ridiculous.  If you find a particularly amazing sale, do remember that you can buy clothing in the next couple sizes down and keep them on hand.  (Pro tip / word of warning:  when you do this, consider the seasons.  If you are buying an adorable sweater two sizes down, do it while winter is upcoming.  Otherwise you will have a cute sweater that you fit into but is too warm to wear.)

There are some great, well-known sites where you can buy cheap clothes too.  Consider buying from eBay or Craigslist.  Search on Facebook for a local page where people buy and sell their stuff.  If you can’t find one, make one!  Undoubtedly there are other people wanting to unload some clothes in every size.

If it is summertime, make the rounds to the garage sales! If you get there early, you can score some amazing pieces dirt cheap, plus you are cutting out the middle man and directly benefiting someone else.

2. Skimp on quality.

How to dress yourself while losing weight

It seems like such terrible advice, I understand. So many times people tell you to invest in quality. Now is not the time to invest in pieces that will last you years because you don’t need them to last years. Consider buying those cheapie clothing pieces that you would normally not even consider because they aren’t super well-made. If it is only going to fit for two months before you shrink your way out of it, the name of the game is covering your body for two months.

3. Learn the tricks to “Make it Work.”

 \How to dress yourself while losing weight

The cheapest way to dress yourself is to use what you already have.  A belt is going to become your best friend.  (Bonus: you get the smug satisfaction of going down a notch periodically!  Yay weight loss!)  That oversized work shirt can be easily transformed by belting it.  That flowy tunic?  BELT IT!  Pants too big?  BELT IT!  You get the idea.  I can’t stress the need for a belt enough.

Another simple trick for shirts is to sew two coordinating ribbons to the back about 6-8 inches apart.  Then, use these as ties to cinch the waists in.  It creates a tailored look almost instantly and is super duper, ultra cheap.

If you are not a sewing type (see my next tip) there are still ways to make semi-permanent alterations.  There is this great product called Heat’n Bond that helps you fuse two pieces of fabric together with an iron and a little spare time.  This is a great option when you need a little tuck there, a shortened hem here, or a simple dart.

4. …Or go full-tilt Project Runway on your wardrobe

How to dress yourself while losing weight

I have recently taken up sewing, and let me tell you, it is not as difficult as it sounds.  I made myself a skirt!  I created clothing!  I am MAGIC.  But teaching yourself the basics of tailoring can help you to stretch your wardrobe for several sizes as you shrink. Seriously, invest in a sewing machine and watch yourself stretch that wardrobe. As a bonus, you will also gain a killer knowledge of fabrics and cuts and styles of clothes, making you an ultra-savvy shopper.

If you lose enough, you might even be able to make something totally new out of your old pieces.  That old button up shirt?  Maybe that becomes a shirtdress for the new skinnier you.  But at the end of the day, if it is too big and you know what you’re doing, don’t be afraid to slice it and sew it. When you have a spare two hours to ogle Pinterest, search “clothing remake” and just browse through ideas. You would be amazed at what your wardrobe can transform into with a little sewing prowess.

5. Shrink your clothes intentionally

How to dress yourself while losing weight

Your momma probably taught you the right way to wash clothes.  Now it’s time to do the opposite!  Take that, Mom!  In general, washing and drying an item on the hottest setting for the longest cycle will do the trick, but just to be sure, Google “How to shrink [FABRIC NAME] in the washer.”  This will likely only work once, maybe twice, but could be ideal for that aforementioned sweater that you bought in the wrong season.

If you shrink an item intentionally and plan to either sell it or donate it, please take out the size tag. How sad would you be if you found a size XXXL shirt and put it on and it was super tight? Didn’t think so.

6. Resell or reap rewards for your old clothes

How to dress yourself while losing weight

To quote the great movie Idiocracy, “I like money.”  So if someone gives me money for an item I no longer need, I feel AMAZING.  There are plenty of ways to get money for your clothes.  You can sell your items online on sites like eBay, Amazon, Twice, Craigslist, or Threadflip.  I tend to prefer brick and mortar establishments though.  The process is quicker, and even though you may get fewer dollars, you get instant gratification.

If you have a consignment or resell shop in your area, USE IT!  Do this for your nicer, trendier items.  Word of warning though, be sure to mentally prepare yourself for the fact that they will not generally accept all your items.  It can really sting when a Plato’s Closet employee tells you that most of the items they rejected were rejected because they are “too mature” for their demographic. Ah, the joys of being 26.

Another overlooked option is the discounts offered for donations.  Many times, thrift stores will offer a discount to those who donate.  I know my local Savers gives a 20% discount coupon each time you donate a bag or bin of clothes.  Since I do lots of my shopping there, it is totally worth it to donate the clothes not picked up by Plato’s Closet or a consignment shop there.

When the wind’s from the east and the sun’s in the west and the sand in the glass is right (come on… name that tune!) you might even consider having a garage sale once you have enough items to sell.  Now, it takes a fair bit of work to put together and your location has to be fairly well-traveled.  But if you have a great location for a garage sale and a weekend to kill, mark those tees down to a quarter and rake the cash in!

7. Stick to the classics and accessorize on trend

How to dress yourself while losing weight

When you are transitioning, you will not have a dream closet of clothes that fit at all times. But what you can do is have a very strategic closet. Choose clothes that can do double, triple, and quadruple duty and work for you. For me, I spend 5 days per week in my work clothes, which amounts to black pants and very specific, expensive, button up shirts from 80 lbs ago. As long as I keep myself in black pants that fit and jackets and sweaters that give the illusion that my shirts are not enormous on me, my work week wardrobe is pretty set.

For the weekends, I have a couple of dresses I can dress up if I am feeling fancy or dress down if I am going casual. The benefit of focusing on accessories is that you can continue to use these throughout your weight loss and even at your goal. The exception here is rings and in some cases shoes. At this point, I have lost enough weight that both my ring size and my shoe size has changed. But investing in some necklaces you love, scarves, hats, and of course, belts is a real win for the wardrobe.

Also consider making sure your wardrobe coordinates. It will allow you an easier time of mixing and matching to keep yourself looking fresh. I like to stick to neutrals and then a few coordinating colors.

An added benefit of choosing classic styles and wardrobe staples is that you will have an easier time when it comes to reselling.

8. Know when to buy

How to dress yourself while losing weight
It is going to be so tempting to buy a piece every time you drop a size, but you just can’t when you are on a budget. Decide to buy a little at a time as needed. For me, this turns out to be about every three pant sizes and every two shirt sizes.

Stick to the items you need to buy first. Save your dollars up for those vanity items for when you reach your goal weight. Once you reach your goal weight, you can focus on buying the cute stuff. In the meantime it is all about keeping it basic.

Another timing issue that might seem obvious but that you may forget in the store is that if you are buying for an event, you need to hold off until closer to the event OR you need to buy something too small and pray that you fit into it by the time of the event. If you are a bridesmaid, you need to have a conversation with the bride about your concerns. I am currently slated to get married in October and have not yet purchased or even tried on a wedding dress. I just can’t even estimate what weight I will be. Trust me. I understand the dilemma fully.

9. Buy styles that will still look good in 25 lbs.

How to dress yourself while losing weight
This is where you have to do a little strategic planning. I have begun wearing dresses and skirts almost exclusively outside of work because they look great at multiple sizes. There are some dresses that I wore 80 lbs ago that still look great today (different, but still great.)
I am a huge fan of the following styles:

10. Change your underwear.

How to dress yourself while losing weight
No, not like that!!! Well, okay, do change your underoos on a regular basis, regardless of weight loss. But I’m going to get down to the nitty gritty here. When you change size, your underwear size changes too.

An entire workout where you pull up your underwear and have to pick wedgies is no fun. Also, your ill-fitting bra rubbing you obnoxiously can make you crazy. Be sure that as you look around for clothes, you don’t neglect to dress the parts of you that nobody will see. Remember that there is a good chance that you will need to venture into sizes, shapes, and styles that are unfamiliar to you. Don’t be afraid to get measured and seek recommendations!

While I am on the subject, invest in a solid pair of Spanx. When you start battling lose skin, you’ll thank me.

There you have it! My ten tips! What are your secrets to being a slimmer, savvier shopper during the transition?



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Kathryn (4 years ago)

I’ve been experiencing a lot of the same problems but in reverse. Any specific advice for us preggos? i have discovered 1 simple, life saving invention though, bra extenders.

    Ashley (4 years ago)

    Bra extenders are great! Thanks for bringing those up! I actually had a helpful employee at Lane Bryant suggest those for weight loss as well: Basically buy bras that were right in the cups and tight in the band and use an extender so that when you get smaller, you can just remove the extender.

    Honestly, I think a lot of these tips apply anytime your body is changing rapidly, like pregnancy. One thing that comes to mind is the tip on learning basic sewing. It wouldn’t be super hard to sew in panels of a stretchy fabric into a top to accommodate your expanding belly.

    A big one for maternity wear on the cheap is craigslist or another community based message board for your area. Many women have had to build a wardrobe of maternity wear, and then a few months later it just takes up space in the closet. Posting an ad or request is bound to get some results from strangers wanting a clear closet and to help someone else out, usually for a very small price.


LoseIt Jane (4 years ago)

OMG! This post inspired me to take some of my clothes from 100 lbs ago and remake them. I’m still getting the hang of it, but I’m excited!

    Ashley (4 years ago)

    Wonderful! Be sure to show us how they turn out!

Misha L. (4 years ago)

#8 Hit Me Close To Home. I Was A Bridesmaid At My Sister’s Wedding And My Dress Looked So Huge! I Should Of Waited To Buy It!!!

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