Why You’re Probably Shopping For Bras & Underwear All Wrong

The foundation for any look is the right lingerie beneath it, but underpinnings are far too often treated as an afterthought. A repeat offender of wearing threadbare, poorly fitting bras myself, I have been thinking more and more lately about how to curate a drawer full of the best lingerie essentials. I want it to feel as intentional and beautiful as the wardrobe I’ve aspired to create.

I’m not proud to admit it, but I once attended a party at a beautiful Italian villa in a couture dress I’d saved forever to buy on TheRealReal — and proceeded to pair it with a random old cotton bra underneath. It was only once I slipped the designer number on that I realized just how much my undergarments (unwisely, the only option I had brought) had brought down the vibe of an otherwise killer outfit.

Like many, I imagine, this period in my early adulthood was spent amassing bras and underwear in a rather haphazard fashion. I would buy things impulsively without ever really considering what the basic building blocks of a well-rounded lingerie drawer would be. Entering my thirties, though, I want to start fresh and have a whole host of questions on how to get started: What sorts of styles should I always have on hand? And for moments when I’m feeling daring, what pieces can double as part of my outfit? (See: the bra and blazer trend.) And what on earth have I perpetually been getting wrong about bra sizing, because no matter what I buy, it never seems to be quite as comfortable as I’d hoped.

If this all sounds a little too familiar, I’ve got you. Ahead, I’ve consulted a raft of experts on creating a comprehensive collection of bras, underwear, and lingerie-adjacent garments you didn’t know you actually needed (but really, truly do). They also point me towards important tips in caring for everything, and reaffirm something I’ve long suspected: the correlation between liking what’s underneath your clothes, and feeling good in them.

Now when I go to get dressed in the morning, I’m starting to enjoy the way picking out just the right support pieces to wear beneath my clothes puts me in the headspace for a great day. I hope these tips give you the same confidence.

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The Building Blocks

One of the first things I did when embarking on this mission was to figure out exactly what I — and everyone, really — needed in my lingerie drawer. Luckily, Cosabella President & Co-CEO Silvia Campello was kind enough to offer me a comprehensive check list. For bras, she suggests the following styles: everyday t-shirt, push-up, racerback, date night (read: sexy), statement, wireless, sports, strapless, and plunge-front. I know this sounds super overwhelming, but it’s actually just nine bras, and you can adjust for your lifestyle and personal preferences. For example, if you’re not one for the gym, ditch the sports bras. Not into the idea of a statement style? No need to pretend.

Campello also advises that you have an assortment of underwear, including everyday thongs and boyshorts, at least one G-string, low-, mid, and high-rise styles, breathable moisture-wicking options (for working out), lightweight pieces for summer weather and travel, comfortable bottoms for sleep, shapers, and sultry date night designs (perhaps to match the bras mentioned above). Again, this list can be tweaked per your lifestyle and general vibe, but the general takeaway here is you probably need more than an economy pack of cotton bikinis from the supermarket.

Next I needed to get rid of all the old lingerie that wasn’t serving me anymore. Fleur du Mal's Founder & CEO, Jennifer Zuccarini kindly acted as my guide. “People hold on to bras too long,” she told me. “So toss those dingy, old bras — especially when the elastic is stretched out and not supporting you.” Going forward, she suggested I consider bras and underwear as the main event of my outfits — they aren’t just something to be hidden under clothes. “You don’t need so many neutral, boring bras in your wardrobe. Think of your lingerie wardrobe as a part of your fashion wardrobe and not something that has to disappear under it.”

Noted. So for someone whose fashion wardrobe trends towards the polished, the feminine, and the flirtatious, what do I need on hand?

Lingerie Sets

From the outset, I found myself immediately gravitating towards sets. I love the simplicity of two matching pieces, and how elevated it made even a simple tee and jeans feel. Luckily, almost every company that makes lingerie offers some of its designs in combination. As someone who likes to have her bras slightly visible beneath a white t-shirt , I found that Bluebella’s Isla set in Electric Purple fit the bill for me perfectly. It’s fashionable, chic, and romantic, while still being infinitely wearable. “Wearing a beautiful matching set — or a clashing set if that’s your thing — makes you feel beautifully dressed and put together, and perfectly yourself,” Bluebella founder Emily Bendell told me. “It’s irrelevant whether anyone sees it or not.”

Galvanized by my first foray into intentional underthings, I journeyed to its high temple, the luxurious lingerie boutique, Journelle. These dreamy boutiques scattered throughout New York City are all beautiful, draped with velvet curtains and designed in soft, romantic tones. There, I picked out the Journelle Victoire Plunge Bra and Victoire Thong, which have rapidly become my favorite “everyday special” (a category I like to think of as distinctly my own) set. Next up? I’ve also got my eye on Simone Pearle’s Rev set in dusty pink.

Bras

When it came to reviving my bra selection, Journelle’s CEO Sapna Palep had some words of wisdom for me. “The most important thing is to be fitted properly,” she says. “Bras also stretch out over time, so just because you have an arsenal of bras in one size at home doesn’t mean that size fits you with a brand new bra.” While in at Journelle, I was fitted properly for the first time since I was a teenager, and found out that I’d been wearing too large a band size and too small a cup. I am happy to report that everything I have subsequently purchased has felt night-vs-day different to the simultaneously too-big-yet-too-small bras I’d been wearing in the past.

I realized during my fitting that there was absolutely no reason I’d slept so long on being fitted in person — literally any store that has a lingerie department should offer this easy service, and one reason that people often get their bra sizes so wrong is that they may simply be resistant to asking. So don’t be shy next time you’re at a store that sells bras! Ask for a fitting — it takes all of 10 minutes — even if you’re not getting anything that day, so you can shop going forward from comfort of your home. There are also plenty of guides to determining your size at home, but honestly nothing beats a consult with a professional.

A strapless bra was also a major hole in my arsenal, so I opted for Cosabella Forte Convertible Strapless Bra in lace, which is both supportive and sexy. As a 32DD, strapless bras and tops in general have long been an Achilles heel. My best bet turned out to be a bra that offered a lift along with full cups and underwire. (Sticky bras, however, are a fantastic option for backless, special occasion gowns.) Additionally, I refreshed my sports bra arsenal with selects from Ernest Leoty, whose elegant styles echo those of Parisian ballerinas, and had me feeling like a new woman in my Pilates class. And finally, I opted for Journelle’s Sapna Plunge Bralette for weekend mornings at home lounging around with coffee and the paper.

Bottoms

Looking at Campello’s list of essential items for my lingerie drawer, I realized I was already doing pretty well in the underwear department. Still, I decided to branch out from my traditional low cut brief and thong routine to incorporate a few more fashionable options into my repertoire. My top pick? The Helas high-waisted brief from Eres, with a matching Deja Triangle Bra, naturally. And for those quiet AMs lounging around at home, another category in which my lingerie drawer was sorely lacking, I opted for Etam’s 360 reversible boyshort.

Finally, I decided that my lingerie drawer wouldn’t be complete without adding Thinx, the beloved brand of underwear specifically designed to be worn during menstruation. The experience of wearing these instead of a tampon was one of the most liberating I’ve had, and an addition I would highly recommend people with periods incorporate into their own routines.

The Extras

But once I started paying attention to my bras and underwear, I realized it didn’t make any sense to upgrade those while leaving my sleepwear and tights in the dust. For hosiery, I turned to beloved stocking designer Falke, selecting a pair of stay-ups for sex appeal, and a pair of classic net tights for fashion. I plan to wear them with more demure dresses come fall and winter for a bit of an edge. It was also rapidly becoming clear to me that I couldn’t continue going to bed in sweatpants. Instead, I wanted a silk slip, and a pair of silk pajamas (breezy linen or organic cotton is another great fabric choice for the summer months).

Another next level addition? A bustier. Feeling ready to take my lingerie game to the next level, I turned again to Etam, as no one knows how to take lingerie out on the town like the French. I took the plunge on their Panama Bustier, and paired it with a blazer and high-waisted pants.

Caring for Your Lingerie

After investing in such quality pieces, I wanted to make sure I was caring for everything properly. “To make your lingerie last longer, hand wash them or put them in a lingerie bag in a delicate cycle in a washing machine – and never put them in the dryer,” Palep advised me. “A good tip is to let them air dry on top of the dryer instead.”

The finishing touch to my lingerie wardrobe turned out to be a delicates wash from The Laundress, a line I had long heard touted for its ability to extend the life of precious garments, not to mention make laundry day downright pleasurable.

Laura Michael, creative director of CUUP, gave me some advice I’d never heard before. “One of the most common mistakes you can make is wearing your bra multiple days in a row,” she told me. “Try to think of your bra like your favorite denim or a pair of shoes — you want to give them time to rest between wears.”

Luckily, with the lingerie drawer I’ve now built out, it’s far easier to take her advice.