A Guide To Buying Your Perfect Bra Online

“Bras are very complicated little garments,” says Sarah Sullivan, creative director of four-year-old lingerie startup Lively. Despite being the reliable workhorses of our wardrobes, the supportive undergarment causes an undue amount of agonizing; wearing one can be a legitimate pain, and finding one that actually fits is a whole new level of headache. If bra-shopping IRL wasn't daunting enough already, our hunt for the perfect brassiere was further thwarted when a global pandemic forced us all into a suspended online-shopping state. Since battling a litany of virtual lingerie options sounds scary, we're here to make this purchase journey as pleasant as possible. Buying the right over-the-shoulder-boulder-holder from the comfort of your own home has actually never been easier, thanks to scores of well-equipped sites that boast encyclopedic-style fit guides and very generous return policies. As Sullivan points out, “the best fitting room is your own room, with your own mirror and your own clothes.” There are certainly some tools, tips, and tricks that will make the online search for underthings a smoother one, which we’ve outlined below. But, rest assured, it is possible to find the perfect bra without getting up from your swivel chair. Read on for the best bust practices and destinations to get it done.

While you may think it requires some kind of lingerie doctorate to determine your band measurement (that’s the number component) and cup size (the letter designation), the math is pretty simple — subtract your under-boob ribcage circumference from the circumference of your breasts at their fullest point, and the number you’re left with correlates to your alphabetical cup size.

It’s best to use a soft measuring tape to find your dimensions, says Sullivan, but if you don’t have a tool that specific on hand, there are hacks: “You could do a belt or a string” — and for measuring, she says, “a dollar bill is six inches [long] — I’ve seen people use that.” A mirror will help you ensure that your measuring tool is positioned correctly, and Sullivan also recommends “wearing either an unlined or very lightly lined bra so that you can see what size you are in something.”

Don’t assume that you’re entering some kind of faceless abyss when you hit a DTC dot-com — your average lingerie e-tailer is probably better staffed than that hipper-than-thou neighborhood boutique with a lone salesperson manning the cash-wrap. Whether it’s a stalwart multi-brand retailer like Bare Necessities or a digitally-native newcomer in the manner of Lively, plenty of online under-shops offer detailed size guides, fit quizzes, and customer-service bots ready to serve up answers to your burning (bra) questions.

Rachel Krause, deputy beauty director at Refinery29, used the “SUPER simple” size chart to figure out her fit at True & Co, and photo editor Kaitlyn Flannagan took advantage of a fit quiz and customer service chat while browsing the mesh wares at culty brand Cuup last month. And, if you miss the experience of face-to-face interaction with an informed under-guru, Lively offers 30-minute virtual fittings where customers can ask questions and have their fit evaluated via video.

Finally, we don’t need to remind you that the world of undergarments is a vast one, replete with bras of every conceivable shape, size, support level, and fabrication. Sullivan advises that shoppers give some thought to what kind of bra they’re looking for prior to diving into the digital shopping experience: “Is it modesty that you're looking for, or extra support, or comfort, or a fashion fabric?” Having some inkling of your criteria before committing your precious moments to browsing will help lessen add-to-cart fatigue.

This sensual startup combines form and function, thanks to suite of “iconically unlined” silhouettes that offer lift and support with an extraordinarily minimal fabrication. You’ve probably spotted one of their high-performance “power mesh” balconette bras on Instagram, but they also smooth microfiber and breathable translucent nylon — all in sizes A - H. They offer fittings (both digitally and in-person, at their New York offices), a fit quiz (tailored for total titty newbies and seasoned bra-fessionals alike), and customer service chat.

An OG in the lingerie e-com space, this multi-brand retailer carries a slew of heritage intimates imprints like Wacoal, Natori, Bali, and Calvin Klein. The full list numbers over 80 brands for a size range that includes band sizes 28 to 56 and cups AA to O. Need help navigating the endless expanse? The shop offers a size calculator, a bra finder that will suggest top-selling styles based on your size, and customer support via phone or chat seven days of the week.

Another longtime digital retailer, HerRoom is a woman-owned, multi-brand destination for tried-and-true undergarment specialists like Chantelle, Elomi, Freya, and La Perla. To help streamline the process of shopping across so many brands, the site developed the proprietary Universal Cup Size system, which helps customers choose the right fit, even with sizing conventions that vary from label and label (and country to country). There’s also a detailed “Know Your Breasts” quiz that will suggest styles based on the unique shape of your ta-tas. Fun fact: HerRoom founder Tomima Edmark also invented the Topsy Tail.

While you might know Knix for their leakproof period undies, shapewear, and sold-out faux leather leggings; let’s not forget they make a slew of top-rated, wire-free bras for working out and lounging. They company modified traditional bra sizes into a simplified numbered sizing system ranging from 1 through 8+. (Some styles are available in XXS - XXXXL+.) The site also offers virtual fittings and customer service chat if you’re stumped by the unique size chart.

As previously mentioned, Lively’s virtual fittings will guide customers through the process of measuring themselves — but, for those who don’t need in-person guidance, there’s a handy-dandy measuring guide and size chart on the brand’s website, along with fit and fabrication guidelines for each of the styles that Lively offers.

While we love the Seattle-based heritage department store for wide variety of wares across fashion and home, their intimates section is not to be overlooked. With a vast selection of both old-school lingerie brands (Natori, Wacoal, Hanky Panky, Calvin Klein) to the DTC newcomers (Skims, Lively, True & Co), the retailer is a one-stop shop for customers looking to mix classic silhouettes with modern options. And of course, they don’t skimp on customer education — they offer virtual fittings and a user-friendly video on how to how to take your own measurements. Still have questions? Consult the Bra Fit Guide landing page for further reading.

ThirdLove’s “Fitting Room” boasts one of the most detailed fit quizzes we’ve seen; complete with questions about changes to your body, favorite brands, current bra size, fit, and age, breast shape, and style preferences. If you feel like doing an even deeper dive, the brand offers plenty of reading on the topic of ta-tas — you can find tk on tk on their Bra Education page. The brand is best-known for its fanatically-reviewed 24/7 T-Shirt Bra, a seriously comfortable, classically-styled, medium-coverage silhouette; the luxuriously soft Pima cotton silhouette, and and uplifting, lace-kissed balconette style.

Does the thought of traditional bra sizing give you a headache? True & Co’s exclusively wire-free bras are available in an easy-to-digest size range of XS - XL — you can determine where you fall on the spectrum using the size chart that lives on every product page, which converts standard bra sizes for easy shopping. The brand’s proprietary microfiber blend feels “super soft and silky,” according to deputy beauty director (and recent True & Co customer) Rachel Krause — and thanks to the brand’s recent partnership with Amazon, shipping and returns are super-easy.