As a fashion editor, I’m constantly thinking about my clothing, which includes my underpinnings. As a bustier woman with a tricky bra size—a 32DD is not a common size—I’m always thinking bra first. When I shop, it’s “What bra will I wear with this?” because I generally don’t go without one.
Similar to the way you think about your clothing wardrobe, you should also have a bra wardrobe to match all of the different things you’ll wear throughout a week. Not all bras are created equal, and one won’t fit every situation.
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I wore the wrong size for years until I learned in a fitting that I was a 32DD (I didn’t even know that was a size). Now I try to get fitted every year because things can fluctuate. If you’ve never had a professional one, stop reading right now and handle that. Going into a store isn’t required: Find a tape measure and do it at home.
Now, the outfits (and bras) I wore this week.
Monday
HEARST
I love to start my work week with a really hard workout because it makes me feel accomplished and helps me set my intention for the day and for the week. Boxing at Rumble is my favorite, and I prefer to do it in a sports bra. I work hard to stay in shape and like to actually see my progress. It makes me work harder.
As someone who’s bustier, I want a style with cups built in because there’s more support. I also like when you don’t have to pull them on and off, because after a sweaty workout you don’t want to feel like you’re stuck in a jungle gym of clothing. This Wacoal style is available in bra sizing too, which is really important if you have a larger chest.
I’ll toss a hoodie on when I’m going to and from my workout so that I don’t feel too exposed. The piping and neutral colors of this one make it look like a regular tank top peeking out.
Wacoal
Wacoal Sport Underwire Bra, $72
Worn with: Outdoor Voices Leggings
Tuesday
HEARST
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I see my barber Tony at Made Men Barbershop every other Tuesday before work, so he’s very familiar with my work wardrobe. When I’m dressing for an average day, I want to look fashion-forward but casual. I never want to feel out of place in a casual office environment.
I love bright knits in general and this one’s off-the-shoulder silhouette freshens up your run-of-the-mill sweater. This bra strap almost looks like a camisole strap, so you can’t tell if it’s a cami or my bra. If you want to show your strap, the key rule is to either go with a dark color or a very purposeful bright, like almost fluorescent.
Wacoal
Wacoal How Perfect Wire Free T-Shirt Bra, $62
Worn with: Mother Jeans
Wednesday
HEARST
There’s a certain cut of sleeveless shirt that just doesn’t work with a regular bra. It hits at a particular spot on your shoulder bone where any bra strap will show a little (and you’re forever tugging at it). Tops like this are where I rely on a convertible style that I can make into a racerback. It lets me be totally confident my bra straps won’t show.
Wacoal
Wacoal Perfect Primer Underwire T-Shirt Bra, $65
Worn with: 3×1 Tank Top, Mother Jeans, Neous Mules, Alexander Wang Jacket
Thursday
HEARST
If I have a big meeting with my boss or executives at Hearst I like to dress up, and a matched suit fits the bill. I’ll wear this to work with a blouse and take it off to go meet my friends for a drink after, keeping the jacket totally buttoned for a little bit of a sexier look. Change into sneakers instead of heels and you’re ready.
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The delicate lacy trim of this bra makes it feel deliberate when it peeks through. It becomes a styling trick, and not just my bra accidentally showing.
Wacoal
Wacoal Vivid Encounter Underwire Bra, $65
Worn with: Manolo Blahnik Heels
Friday
Hearst
Friday dressing is always about a look for the office that I can wear out to date night later. For this jumpsuit I wanted a bra that will give me some lift, but isn’t vulgar, especially because I’ll be wearing it to work before getting dinner with my boyfriend. This one has wider straps that won’t slip and is super lightweight.
With a v-neck, also look for cups that don’t come up too high. They shouldn’t be visible or interfere with the neckline’s clean canvas. That open spot of skin is perfect for highlighting jewelry, like these gold necklaces I wear everyday, and I don’t want my bra to be distracting.
Wacoal
Wacoal Awareness Underwire T-Shirt Bra, $68
During the month of October, Wacoal will donate $2 to Susan G. Komen® with the purchase of any Awareness bra.
Worn with: Frame Jumpsuit
Saturday
Hearst
For brunch with my girlfriends I like to be cozy and casual, but not sloppy. An off-the-shoulder sweater is the best of all of those worlds. I was inspired by a runway look that had a corsetry vibe when I got dressed. This look is subtly sexy because you can see the bra straps and they hint at something sexy underneath, but it’s not so much that it doesn’t work for daytime.
I’m more of a conservative dresser by nature, so this is a way for me to dip my toe into the lingerie-dressing pool without diving into it headfirst.
Wacoal