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?

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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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