How to Shop for Clothes While Losing Weight

how to shop for clothes while losing weightIt can feel like a hard-fought victory to lose weight — but buying a new wardrobe for every size on the way can be an expensive habit! So how can you look stylish and put together while your weight is fluctuating? Reader K wonders how to shop for clothes while losing weight…

I’m in a male-dominated business casual office. I am getting ready to start positioning myself for a promotion and want to up my dressing game this summer. I’ve lost 40 pounds (yay me!!) and want to lose another 30. I’d appreciate any advice on managing a transitional wardrobe as I lose weight. I’d like to watch my spending before I hit my goal, but also look pulled-together and not be frumpy. Bonus for ideas that work well in a pretty hot part of the country!

Great question, Reader K, and CONGRATS on your huge accomplishment! We haven’t talked about how to step up your wardrobe for a promotion OR about favorite weight fluctuation clothes in a while, and I can’t wait to hear what readers say. For now, here are some thoughts for you:

How to Shop for Clothes While Losing Weight

How to Shop for Clothes While Losing Weight Tip #3: Wear Wrap Dresses

Pictured above: one / two / three / four (affiliate links***)

  • Look for these signs for when to retire or tailor a piece that may be too big:
    • Hems are dragging on the ground or permanently turning up.
    • Skirts are turning around on you entirely.
    • Armholes are gaping and showing your bra (although this may be a simple fix for the tailor depending on the garment; stop in and ask!).
    • Non-drapey fabrics (particularly lined ones) are draping.

You know your career, weight loss schedule, and budget the best — but I will encourage you to resist the impulse to shop exclusively at fast-fashion chains and instead look to secondhand or consignment stores to reduce the financial impact of your quickly changing wardrobe. (You may find better quality stuff there anyway that will be worth it to you to take to the tailor for alterations!) Depending on your size range, you may also want to look into a clothes rental subscription at a spot like Gwynnie Bee, Le Tote, or even Rent the Runway.

Readers: What advice would you give Reader K about how to shop for clothes while losing weight? What are your best tips in general for what to wear to work when you’re losing weight, or what to wear if you’re looking for a promotion? 

Picture via to shop while losing weight tips and advice for work wardrobes

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Losing weight is hard -- but looking polished while losing weight is harder! We rounded up our best tips for how to shop for clothes while losing weight, all for a reader looking to step up her wardrobe for a possible job promotion. What are your best tips for how to shop for clothes while losing weight? Come share them with us at Corporette.


  1. I think it’s like pregnancy; you recognize that there’ll be frequent changes to your body (until you’re at your goal weight or the weight you choose as your long-term weight), so buy inexpensive professional items from places like target or thrift stores, so you can look right at work without spending tons on clothes that won’t fit in a few months. In addition, make sure you donate/get rid of items once they no longer fit you so that you don’t end up with a closet full of cheapie wrong-size items in your way!

  2. Anonymous :

    A basic ponte blazer did a lot of work for me in this situation. Nice enough to look polished, but forgiving in fit as your size changes. I had two of them, one in black and one in gray, and I wore each of them at least once a week for a few months as I was changing sizes. Target has some solid ones, and I actually got my black one at Forever 21. Olivia Moon at Nordstrom also makes a solid and inexpensive ponte blazer.

    • JuniorMinion :

      Asos has some good ones as well – I am in their straight size versions (washable yay!) but it appears they have the same sort of brushed ponte blazers in their curve line as well depending on what size the OP is.

  3. Anonymous :

    I am in the midst of losing weight and have found I can still wear my skirts but my pants are a problem. This is especially true for skirts that were high waisted; they just sit lower on my waist now. In the past I have also had success with getting a couple bigger ticket items altered by a tailor. This is most likely to be easy if the garment doesn’t have a ton of seams – like a skirt with just side seams (and maybe darts) is likely going to be easy to alter than one that has princess seams.

  4. I recently lost 55 pounds (on a 5’9″ frame, so admittedly, not as drastic as it sounds) and went from a 12 to a 4, and a few things I found that worked well for me:

    – Skinny jeans/pants – I found I was able to get away with only buying every other size + a belt at the smaller size. The tight legs helped keep things from looking totally out of whack. This way I only bought 12 + 8 + 4, rather than every size in between as well.
    – Flowy tops in size s/m/l – similar to the skinny jeans – I could get away with a size medium top basically from size 10 to size 4 – I just switched to smalls right at the tail end of my weight loss.
    -A-Line dresses – I didn’t have a ton of luck with wrap dresses (I just don’t like them very much), but I was able to get away with a-line dresses pretty easily through a few sizes – a size 12 was a little big when I should have been a large 8, but it was still wearable, and adding a cardigan covered it pretty easily. I could get away with only doing a 12 + 8 + 4 that way too.

    • Co-sign the 2 sizes thing. I fluctuate between a 0 and a 2 every few years, and I just buy things in a 2 and belt or throw a blazer over everything to hide the slight bagginess.

    • I was a 14 I’m now a 10, all in a matter of 6 months. Still loosing, but also TTC so the loss is temporary. For that reason I’m reluctant to have anything taken in. I’m sticking to my sheath dresses. I’m in a 14 today. I don’t look frump-tastic, but could look better. I save my well-fitted stuff for important, client-facing days. A boyfriend cardigan is hiding the extra material and slightly gaping arm holes for the time being. It’s not perfect, but I refuse to shell out more money for another few months.

  5. AttiredAttorney :

    I got the tip from someone in this group, but there is a great facebook group about how to find cheap clothes on amazon. Many are stitchfix knockoffs, but they also have some items that are good for work wear. The one I like the best is called “Name Brands for Less! Women’s Clothing & Accessories.”

    Also, for “disposable” dresses (to wear for just a couple of sizes), I have had a lot of luck with the sales at JCPenney.

  6. Shopaholic :

    I don’t wear pants to work at all, primarily because of the weight fluctuation issue. But you can still wear a skirt that is a bit big, even if it doesn’t look the best. Also fit and flare dresses and wrap dresses fit through a range of sizes.

    Plus, I think flowy tops are in right now. The ones that are a bit big, I can just tuck them into a skirt and it looks pretty good.

    • This is a good idea. When I wear pant’s to work (usueally in the winter or on Friday’s ), men always stare and whistel at me and make clicking sounds with their tongue. For some reason they think that I will be mesmerized with their clicking sounds? FOOEY on that!

    • +1

  7. Another option would be a subscription box service like Stitch Fix or Gwynnie Bee (which does sizes 10-32). You can try various styles, return them right away if you don’t like them, keep them a while if you do, size down when you need to, and ultimately buy things if you want them permanently.

  8. I am just about at goal, after losing 80 lbs over 18 months. Two things that worked for me — eBay (search for any brand and “NWT,” which is “new with tags”) and vintage items on Etsy. My two best finds — a classic Pendleton blazer for $35 and a NWT Dorchester tweed blazer for $50 that still had a $500 tag on it. Consignment is another option.

    For me, it was important and motivating to get rid of clothes as soon as they were too big, and to make sure I always had something that fit perfectly.

    I also shopped sales like crazy and got basic, solid color separates that could be changed up with accessories. Just shopping for new clothes was motivating.

    Congratulations on your success to date!

  9. What about wardrobe rental like LeTote or Rent the Runway Unlimited?

  10. I buy business appropriate printed jersey dresses (Ralph Lauren has some excellent examples) a size too small and wear it until it’s a size too large. The print camouflages the sizing and the jersey fabric is forgiving enough to stretch. Throw on a blazer and I can wear the same dress for 20 lb fluctuations (10 lbs = a size).

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