Style + How To Wear It

The Rules for Dressing When You’ve Gained Weight

Since finishing law school two years ago, I’ve gained 30lbs.  When I’m naked, I actually feel pretty good about my body.  But when I put on clothes, it’s a whole different story.

And dressing for summer, when you don’t feel the best about your body, is its own special torture.  What’s a girl to do?

When you’ve gained weight that you plan to lose (at least that’s what I keep telling myself), buying clothes can feel like a poor investment.  Why spend $150 on a dress that is going to be a size or two too big post weight-loss?  But there are some rules for buying clothes when you’ve gained a bit of temporary weight.

Rule No. One: Try on Everything.  You can no longer just stumble into a store and grab “your size” off the rack.  Clothes need to be tried on, assessed, sized up, perhaps tailored.  If you need a cocktail before this torture begins, then so be it.  But thinking that you have a definitive size is just going to crush your spirit when said size isn’t quite right.

Rule No. Two: No One Sees the Tag.  Do I like buying larger sizes?  Of course not.  No matter how enlightened I may be, I am not immune to the slings and arrows of a culture that praises skinny.  But just remember fit is what matters.  No one can see the tag but you.

Rule No. Three: Dress the Body You Have. When I tell people I’ve gained weight, they’re flabbergasted.  I don’t look like I’ve gained more than a couple of pounds.  This is because I’m dressing the body I have, not the body I want.

Rule No. Four: Seams Are The Enemy. The fewer seams a garment has the better.  Pants have two leg seams, a back seam, and a waistband.  A skirt has two side seams and waistband.  Why do these differences matter?

First, the seams are where a garment gets tight.  So a skirt that’s a little small is less uncomfortable and more flattering than pants that are a little small.  Second, a skirt is less expensive to tailor when you lose the weight than pants are because there are fewer alterations to make.

Rule No. Five: Know Where You Gained Weight. I carry most of my weight in my hips and thighs.  Sadly, I’ve gained so much this time that I have belly fat and bigger breasts to contend with.  This meant that I had to completely rethink the shapes I was wearing to address these new concerns.

So what am I buying for summer?


Wrap Dresses, lots of wrap dresses.  Wrap dresses are comfortable (no waistband, no tight seams), and adjustable.  I size up for the best fit, and then tighten as need be.  If I need a bit more structure, I cinch the belt, but don’t knot it, then safety pin the ends flat, and add a wide belt over the top.

This red floral Band of Gypsies ($98) dress is one of my best recent purchases.  It can be worn casually with a flat sandal and a wide belt.  Or I can dress it up with a pair of chunky heels and a blue stone bracelet to bring out the blue in the floral pattern.

This yellow Ann Taylor dress ($149) gets looks when I wear it.  The bright color, the flirty shape — why shouldn’t people stare? It’s also versatile enough to wear to work, to church, to weddings, and to brunch.  For work, I layer on a white or navy blazer and a skinny belt at the waist.  For weddings, a dramatic green earring and a neutral heel.

The Karen Kane Faux-wrap ($108) isn’t adjustable, but it’s so forgiving that you won’t care.  It’s the perfect work dress because it always looks good and has a sleeve.  I’ve sung this dress’s praises many times, but if you need another reason to buy it, try this one: I gained 30lbs and my original one still fit.  Hello, stretchy fabric.  It also comes in plus-size.

Need plus-size wrap dresses?  Try this J.Lo midi-wrap in a pretty purple floral or this yellow-dotted dress from Lane Bryant. Petite?  I like this Felicity & Coco Wrap Dress and this floral New York & Company dress.

The nice thing about all of these dresses is that they will fit with minimal alteration or no alteration after I lose some of this weight.  And for the time being, I feel really comfortable and pretty when I wear them, which is such a boost to my daily happiness.

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  1. Mica says:

    Needed this. I’m 63 months pregnant and I have to keep stopping myself from purchasing clothes until I find out what this body’s gonna look like. I know I definitely won’t be my pre-pregnancy size and I’m having to accept that.

    June 19, 2018/Reply
  2. aar1 says:

    Thanks for this Belle. I switched jobs from firm to in-house a few months ago, and I have come to learn that lessened stress for me means a bit more jiggle. As rational as my brain is, there’s something defeating about the body changes. But I still get joy out of lovely dresses, and this post has nudged my perspective the right way.

    June 19, 2018/Reply
  3. Denise says:

    I’m up maybe 15 pounds or so since having my second child (and no, it’s no longer baby weight…and maybe at 41 it might not come off), and I very rarely wear slacks any more. I work in technical sales in the chemical industry so I do have 2 pairs of slacks that I wear to customers, otherwise I’m in dresses. SO much more comfortable! Of course I live in a warm weather climate so I can get away with this year round!

    June 19, 2018/Reply
  4. Kate says:

    You literally read my mind today! Every single word! I only wish it came a day sooner before I packed for a business trip without following Rule #1 (even while shopping my closet). I did pack one wrap dress, which I have been wearing with a belt since you gave that tip years ago :), and as you mentioned the skirts don’t look too bad.

    June 19, 2018/Reply
  5. C says:

    I’d highly recommend looking into a subscription rental service, such as Ann Taylor’s Infinite Style, when your sizes are fluctuating! It’s nice to feel like you have new clothes without committing to a certain size.

    June 19, 2018/Reply
  6. Lindsey Baker says:

    This was a great post, thank you. I’m almost 10mo post baby and while I’ve lost most of my weight, my belly might never be the same… sad face. I appreciate when you do things like wear this item with these 3 things for work and swap for these 2 for play. And I have the Karen Kane dress too, on your recommendation! It is nice to see new items on the blog, but I also like when you repeat/re-purpose items – I can’t always buy everything new!

    June 19, 2018/Reply
  7. AMber says:

    Re: rule 2 – I would add that numbers on the tag have little basis in reality today. I just went shopping at a mall recently and bought clothes in sizes all over the place – small, large, 28, 6, 8. They all fit the same! It took many years, but at 37, I have finally decided my self worth is more than a number on a tag.

    June 19, 2018/Reply
  8. A says:

    I can’t stress enough that excellent point that “no one sees the tag” of the size you wear! Buying clothes that fit me and not the number I used to wear is such a revelation; I wish I’d learned this lesson in high school.

    I hope you feel happy and healthy, no matter your weight – everything else is gravy!

    June 19, 2018/Reply
  9. Jules says:

    Great tips!
    For me, I’ve also found that wearing fun, bright colors, or interesting prints helps ‘camouflage’ my weight gain. It’s like an optical illusion – I distract people with my fun colors and they don’t notice my weight 🙂
    It works.
    I also only wear skirts and dresses that have some stretch in them. It helps it stay comfy when I gain, and *if* I lose weight, it will still fit when I’m smaller.
    Sadly, I’ve had to kiss goodbye to shorts though, for the last four years. Shorts are my favorite, but I now can only wear capris 🙁

    June 19, 2018/Reply
  10. CR says:

    thanks for this post! I’m dealing with this as well. I’ve decided to just buy some clothes in my new bigger size and make piece with it, rather than feeling unhappy when I try things on…

    June 19, 2018/Reply
  11. M says:

    Rent the Runway subscription service has really helped me this past year when my weight has fluctuated a lot

    June 19, 2018/Reply
  12. Erika says:

    Yes to everything! At 42, my body has changed. And because I’m 42, I don’t particularly care.

    But, Belle, let me ask this: since the area right above my knees suddenly started doing something weird, I no longer love dresses and skirts without tights. And I’m rather short-legged, so mid-length skirts and dresses look frumpy on me, no matter what shoes I wear.

    Combine this with the introduction of your seam rule … and I am stumped.

    What is the pant equivalent of the wrap dress?

    June 19, 2018/Reply
  13. Erika says:

    This is such a welcome post for it is a reality! I too have gained recent weight, mostly in the stomach region, and would like to think it it temporary. My tips for dressing would be buy dresses too, but go for Shift, A-line, and Sheath styles. V-nexks are always flattering. Simpler is better, so less ruffles, patterns, and seams. I agreed that fabric is key, and buy the best you can afford so it either provides structure or lots of give (and doesn’t look cheap). Accessories tend to be what people notice with a dress like this or the color. It is all about keeping people’s eyes where you want them.

    June 20, 2018/Reply
  14. shannon says:

    Thank you for this. This winter was the worst ever! I typically gain in the winter but just so that my usual clothes feel “only snug”, and it’s usually quick to come off by the summer. Not this year! Even my shoes were starting to feel tight!

    Not being a dress/skirt person, the transition has been tough on me. I like dresses but I just feel so exposed, and often cold. Also being short in stature, dresses with flats make me look like a gnome. So I’m then forced to go with heels to elongate the line.

    I love the idea of buying a slightly bigger piece and tailoring it down to fit all the parts of you. Not sure why I hadn’t thought of it before… but thank you for bringing it to my attention.

    June 20, 2018/Reply
  15. Shandra Herrod says:

    Thank you for this post! I been feeling down after gaining several pounds traveling frequent for a new job. I’m going to close weight but need to find a few items for now to wear to work. Job well done.

    June 20, 2018/Reply
  16. Liza says:

    Thank you for articulating the internal struggle I’ve been having with the 20 lbs of baby weight + medication weight gain before that that has me up from an 8 to a 12! I actually don’t hate how I look naked either but my all my beautiful structured dresses that I used to wear for work I can’t even get over my hips. I’ve been working on giving myself grace and trying to buy a few high quality things so that I don’t hate my weight AND my wardrobe in this new reality. The dresses are a good call, and I agree with the commenter who mentioned shift/sheath and a-line dresse. They give you freedom and if draped right will hide some jiggle 🙂

    June 20, 2018/Reply
  17. MWH says:

    Thanks for this. The seams tip in particular is a good one, and a new one to me. You’re a true friend to busy women!

    June 20, 2018/Reply
  18. Jess says:

    This is helpful, and you are awesome for addressing it. Love your blog.

    June 20, 2018/Reply
  19. S says:

    This is so true! I actually have the opposite problem right now because I lost a significant amount of weight for my wedding (dropping 2-3 dress sizes depending on the brand). I am really skiddish about buying new clothes because I’m not sure that I have the willpower to keep up my new diet now that the wedding is over. So I have implemented the adjustable, wrap-dress rule for sure! I am also able to wear the types of clothes you listed above much more easily and wish I had purchased more of them before the weight loss.

    June 20, 2018/Reply