By Fawnia Soo Hoo
Updated Mar 07, 2016 @ 5:30 pm
Kate Upton sighted arriving at the Vogue Festival on April 26, 2015 in London, England.
Credit: Fred Duval/FilmMagic

We love the classic button-down shirt (it's currently enjoying a renaissance on the runways), but sometimes it can feel so, well, buttoned up and structured—as in no give, which can be problematic especially for girls who have a bit more going on in the bust area. But hey, Kate Upton and Christina Hendricks have been known to rock a really good button-down shirt that fits flawlessly. What's their secret?

To investigate, we consulted the cool-girl's tailor of choice, Erin Hogan-Braker, who's basically a cool girl herself. The Greenpoint, Brooklyn-based authority took time out of her busy schedule working for her celebrity clients (aka Jennifer Lopez and Ciara) and fashion brands, like Victoria's Secret, for her company 7th Bone Tailoring and her individual customer service Stitched Up, to share some insider pro-tips. And guess what? Hogan-Braker's thoughtful advice on scoring the perfect shirt applies to all of us, busty or not.

Look for a Shirt That Fits Over the Largest Part of Your Body

Hogan-Braker's rule of thumb for everyone and all types of clothing: Make sure the piece fits over the largest part of your body. "Because it’s easiest to take in clothing when you’re doing alterations and tailoring," she says. "It is more difficult to let clothing out because there’s less fabric to work with." So that applies to a dress fitting over the hips or shirt sitting comfortably over the chest area. And make sure you can move, so swing your arms around, sit down, cross your arms, whatever. If you have a large bust, try the shirt on and make sure the material doesn't pull and leave bra-exposing gaps between the buttons. And if the waist or arms are too baggy, just ignore it, "because that can easily be done through tailoring." Which leads to...

Find a Good Tailor

Having a regular tailor might seem like a luxury reserved for only Claire Underwood or a hedge fund billionaire, but Hogan-Braker wants to you to know that everybody can—and should—have a tailor. "It’s kind of a new concept," she says. So to find one that's right for you, she recommends "auditioning" tailors, similar to finding a hair stylist or even a doctor that you feel comfortable with and trust. Hogan-Braker suggests bringing a prospective tailor a piece of clothing you're not that invested in to assess their work and results. "You’re basically looking for someone who is open-minded and willing to listen to what you would like out of the experience," she says.

Have the Tailor Fix Your Shirt to You

At the tailor, that baggy waist, the voluminous arms, droopy shoulders and any other unshapely elements will be taken in and fitted to your measurements. Added bonus: This strategy works on any type of fabric or weave—​cotton, silk, or synthetic—so don't feel limited by what you read on the tag. "I like to say that if you have a tailor, the fabric choice and the size on the label is no longer an issue because they can take that fabric and they can recreate it for your shape," Hogan-Braker says. "It gets rid of this obsession of looking at sizes and trying to fit into this size—you no longer have to fit yourself into the clothes, the clothes now fit to you."

Consider It an Investment

Hogan-Braker does admit that a tailor is an added expense, but it's also "an investment in your closet." Basically, you'll have pieces customized to your shape, taste and style, which means you'll want to wear them (a lot). Plus, "you can go to vintage stores or more affordable retailers for inexpensive garments and then have them tailored—and they'll look more expensive," Hogan-Braker says.

Contact Erin Hogan-Braker at or