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How Do I Dress While I’m Losing Weight?

Posted on January 29, 2024

I recently started losing weight, and am having trouble figuring out what to wear. It seems foolish to invest in clothes before I finally stabilize again, but wearing things that are too big not only doesn’t look good, but is not good psychologically. Any suggestions? — Paula, Milwaukee


Changes in your body, whether intentional or not, are intrinsically connected to changes in your emotions and sense of self, even before you start taking into account social messaging around weight and physical beauty.

Altering your shape can alter your identity in pretty essential ways, and since identity is expressed in part through clothing, losing weight (or gaining it) sets off a domino effect that is about more than just size. It’s also about how you communicate who you are to the world: whether you are happy or sad; whether you want to bare yourself, hide yourself, armor yourself, decorate yourself; whether you want to turn yourself into a goth, a prepster, a sophisticate, and so on.

That means any clothing purchases related to your new size should be made with care and deliberation. Well, that should be true of any clothing purchases, period, but it’s especially true when you are dealing with a different you.

You really need to live in your body for a while before you decide how you want to display it, because how you feel initially may not be how you feel later, and wardrobes can be, as you point out, an investment. Of both time and money.

But what to do in the interim?

It’s easy to see fast fashion as a quick fix: a jolt of serotonin when you are feeling unsure about who you are or how you will be received. After all, it takes less commitment, and changing your body doesn’t affect just you but also your relationships and how your friends and colleagues see you. Literally. But in the long term, such a stopgap solution is probably just a waste, in all meanings of that word.

According to a study by Statista, 23 percent of American women and 19 percent of men buy clothes they never wear. My guess is that this is in part because what can seem perfect when you are surfing shopping sites at night or on your phone while taking the subway can also seem, in the stark reality of every day, uncomfortable and obvious. So it gets relegated to the back of the wardrobe or to the landfill, never to be seen again.

For alternatives, I asked Ines de la Fressange, the famously chic designer and former model, what she would suggest. “Men’s clothes are the solutions to everything,” she said.

Specifically, she advised investing in a classic button-up shirt from a brand such as Hilditch & Key (“the pink ones are usually on sale”), which you can then wear as you want: oversize and loose, perhaps with leggings that accommodate a variety of body shapes, and then belted, tucked in or even tied.

Along with the shirt, she suggested a pair of loose khakis that can be worn either on the hips or cinched at the waist with a belt or scarf and one good jacket or unlined coat for a bit of tossed-on-top polish. Just make sure whatever you pick fits in the shoulders.

Kate Lanphear, the women’s style director of T magazine, also advocated investing in a jacket, though she suggested pairing it with a jersey wrap dress (the sort that made Diane von Furstenberg famous) that can be adjusted according to your needs.

The point is: These are pieces that transcend size and provide a base line on which to build. When you are ready.

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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