As trendy women, our main focus is to keep our clothing brand-new, stylish and in-season; but do we always give the same consideration for our intimate attire? By now we should understand that the most important garments are what the public can not see. That’s why Macy’s has introduced Fit Matters for women who care to be fashionable and comfortable even under their stylish outfit.

Visit to find an expansive line of intimate apparel and expert advice from fit specialists (which you can get in-store as well).  Finding the right bra is not easy but with expert advice, you’ll find the perfect one for your shape.  The quest is worth the end result!

Watch this video of real women talking about their embarrassing “oops” bra moments.

Enter to Win:
What is your oops moment? Whoever shares the best “oops” bra moment story/picture wins a $25 Macy’s giftcard!  (Yours to spend how you like but I suggest applying it toward a new bra!)

Deadline to Enter:
March 31, 11:59 PM
US Residents only, please.

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TAMMY GIBSON, founder of A Mom in Red High Heels, is a God-loving, coffee-drinking, heel-wearing, wife and mom offering up her best tips to help women look and feel fabulous so they can achieve their biggest dreams.


  1. My husband had worked late the night before, so I dressed for work in semi-darkness so that he wouldn’t be awakened. My day ahead was manic. I was heading out to take the kids to school, a quick food shop, and then to a funeral. I never once checked out my reflection in the mirror ….too many kids, too many errands, too many things to do ….and when I finally did look, I saw that I’d worn black pants, and my beautiful fuschia pink lacy bra under a white shirt. I could have sworn I had put on my black bra and black shirt. It was totally Madonna/Like A Virgin inappropriate for a funeral, not to mention a carpool of teenage boys. Major oops bra moment.

  2. susan varney

    i got drunk at a frinds house took a shower to supposedly sober up and put my bra on backwards after. no blouse only the bra and my skirt when i went downstairs

  3. Renee C.

    I am not one to throw out a “perfectly good bra” but apparently one of the bras in my drawer was no longer perfect and no longer even good. While at work I was working in a counseling environment with elementary school kids playing some games when I heard POP and my front clasp bra had completely come undone. It was a MIRACLE bra so it was pretty padded and there was no subtle way to fix it or hide what had happened I stopped the game and kept my arms crossed for the remainder of the session and then RAN to the bathroom to “fix” myself. No longer do I buy front clasp bras and no longer do I hold onto things well past their prime.

  4. I don’t even know why I am admitting this but.. one night when i was going out with friends into Boston.. I put on a low cut shirt and i definitely have no cleavage so I put socks in my bra to lift my gals up a little.. well I ended up having a few drinks and wasn’t too aware of my top haha so while in the bathroom, coming out of the stall after I had bent over to squat down.. some random girl pointed to me and said UM YOU MIGHT WANT TO FIX THAT BEFORE U GO BACK OUT THERE.. and i looked down and my sock was hanging out of my left cup 🙁 haha least she saved me the embarassment of a guy catching it! haha

  5. Oh Lord, so I went bra shopping with my mom in December when I went home to visit. I dropped something & bent down to pick it up & didn’t realize the doors had a huge opening at the bottom (the door wasn’t from the floor to roof). My stupid self was braless when I bent over to pick something up & my mom was yelling at me to stand up & away from the door. LOL We were laughing so hard we were crying. I felt my face get tomato red! Now I HATE trying on ANYTHING!

  6. Danielle

    I was a replacement bridesmaid in my friend’s destination wedding since her sister could not make it at the last minute and I am roughly the same dress size. Problem is her sister is chesty and I am not. Lets just say there was some major gap-age going on in the top of the dress.

    Of course to save myself shame (or so I thought) I wore my padded strapless bra with the dress to help me fill it out. Great idea right? Ya, thats what I thought.

    Halfway down the isle the bra migrated south into the top of the dress. 100+ people staring at me and my double boobage. As you ladies know those padded bras keep their shape so imagine the twins, with another set of “twins” directly beneath them. I had 4 boobs!

    No real way to run back and hike up the bra so I spent the entire ceremony squirming and trying to make it less obvious hoping at least some of the guests did not notice.

    And while the memory may fade in their minds the photos will last forever!

  7. Alejandra

    I was in a beach volleyball league last summer and there was a really cute guy in my team. One day I decided that I was going to wear something a little cuter than my regular racer back tank and sports bra. So I put on a cute strappy tank top and a front clasp bra that made my cleavage look really nice. WELL needless to say within 5 minutes of the first game the bra broke and I had to play the next 6 games with my 38Ds flopping all over the court!!

  8. Jennifer Jones

    I work in a job where we have a lot of events with semi-famous people, including celebs, journalists, and politicians. I was supposed to speak at one of these events, but I had been up so late the night before getting ready, that I was extremely tired the next day. I was so tired in fact, that I totally forgot to put a bra on the next morning. I wore a business suit, but I’d taken the jacket off right before I was supposed to go on stage. I was speaking at the podium when I realized that I was wearing a semi-see-through blouse, no suit jacket, and NO BRA. And this was a WORK event. Ugh! I was so immediately embarrassed that I messed up on my speech and made a VERY quick exist off the stage. It was easily the MOST embarrassing moment of my life!

  9. Heather M

    Ok well… I bought My first Push Up bra… I bought it a size smaller because bra’s don’t fit me that great. Well, My father was over my house and I bent over and My Boob popped Right out of my cup (and out of my SHIRT) So my nipple was completely exposed to my DAD!!! I had to run in the bedroom and fix it. And Yes he Saw it! BLUSH

  10. meredith

    Oh man, these stories made me laugh so hard. One night a few years ago I went out with my Army boyfriend drinking. We were totally trashed and in one picture my bra was totally showing, thankfully it was a rockin’ bra. LOL

  11. Wow, who hasn’t had a bra oops moment. I have a bra that has 2 ribbons you can tie into a bow in front, all very cute. One day I felt this brush against my stomach while in a group of people and thought I had a bug up my shirt. I hopped around and tried to flap the bug out of my shirt but soon realized that it was my cute ribbons that had come untied and were brushing against my stomach. Talk about over-reacting then not wanting to explain what the hoopla was about.

  12. Marilyn Wons

    My best story was when I was playing tennis in a match, by bra snap broke. I could just feel it slipping down my top. I had to be on the tennis court for fifteen more minutes. This was a team match so the bleachers were full of people. It took all I had to concentrate on the game and overlook my mishap. I actually won the match, probably because I wanted to get off that court as soon as possible. After that match, I only wore pullover bras to matches!

  13. Cynthia C

    Nothing too extreme, but I once wore a strapless that kept riding down and had to be hiked up at frequent intervals. Very annoying!

  14. I had this bra, it was old but it was my fav, the back closure was starting to rip but I figured it was my fav so I would continue to wear it. Well I had a lot of things I had to move at work and was constintly moving around. While moving some of the items I hear a hint “snap” and then I felt no support from my bra. The closure had finally ripped away completely (OMG). Luckily I only live about 3 miles (10 mins) away from work. I just took a VERY early lunch and went home to put on a different bra. To this day I am not sure if anyone else knew what happened to me…Thank goodness. I was so embarrassed!!

  15. This doesn’t happen a lot thank goodness but once in a while one of the “girls” comes out of the cup and I can’t always put her back right away depending on where I’m at!

  16. When I was in college a class I was in took a tour of a local hospital. It was a Loooong tour. My back was killing me from standing for the hours we had… our next stop was the EKG monitoring. They asked for a volunteer to lie down on the table so they could show everyone how it worked. I raised my hand as I just really wanted a chance to sit. What I didn’t realize is they then lifted my shirt and the whole class got to see I was wearing my ugly bra that I loved and really needed to throw out. It actually had a safety pin holding the strap to the cup. The HORROR!

  17. Years ago, in high school, I was giving a report on Salem MA, and I was standing up in front of the class. Keep in mind, even as a Junior in HS, I had bigger boobs than most of the girls in my class. During the powerpoint presentation, one of the straps of my bra broke. Literally snapped. Mid-sentence, I felt it, and sort of froze. It probably looked as if I had stuffed my bra and a sock/pad got dislodged. I remember a few of the girls giggling, mostly the boys just gawked. I blushed a deep red, finished my presentation which felt like it took an hour! and then I went to the bathroom, and had to make a makeshift bra strap out of tying the broken strap to a headband. Mortifying! Funny looking back on it now though.

  18. Stephanie V

    Tried team golfing with some fellow students and professors for first time many years ago. Was doing all right (beginners luck) when at the 6th hole prepared myself for a swing and SNAP! Yep, my bra strap broke. My girl went a-hanging but I kept a-swinging. Had to finish the day with one girl up and one girl down but never did I tell anyone.

  19. Jackie C.

    Two years ago, I was getting ready for a night out at a club with friends. I had a strapless dress on and I had to wear my worst strapless bra because the other one needed a wash. I wasn’t too worried because it felt like it was staying up fine. Much free glasses of champagne later, I was drunk and vomiting because I didn’t have much to eat beforehand and I had a slip, exposing myself to my girlfriends only thank goodness! Still, I was a bit embarrassed and looked like a fool. I hate that bra. I need a new one that fits well!

  20. I’ve really only had one embarrassing bra moment. When my dog was a puppy, I wore a stretchy V-neck top when I took her to the vet one day. I was holding her on my lap because she was too small to be hanging out on that germy floor! She kept squirming because she wanted to get off my lap and play, but I was holding her tight. I was sitting there, minding my business, when I looked down and suddenly noticed that my puppy had hooked her paw on my neckline and had pulled my shirt down to expose my whole left boob. I have no idea how long I was exposed because I had been daydreaming looking at the posters on the wall and everything! And it was a lacey see-through-ish bra.


  21. I like bras that close in the front because it’s easier in the morning to get dressed. Well, a few months ago we met some of my husband’s relatives at a casino. My bra unsnapped and my blouse button popped off within seconds…..I ran to the restroom fast. I had to secure the bra and the blose with several safety pins (Thank goodnes I had a few)……and was too embarassed to explain why I suddenly ran off!

  22. I was one those people who actually stuffed their bra. That O.K. if the stuffing stays in if you know what I mean.

  23. Jennifer

    After I got married, we had a fabulous party to celebrate when we got back from honeymoon. My dress was backless, and I had to use those terrible stick-on bra things. I’m not that well endowed, so I thought it would be fine. Right. After a little while, which included some dancing, and most importantly a very sweaty horah, the silly things were slipping and sliding all over. Not good. I was pretty much hanging loose the whole night, which made me very uncomfortable and self conscious and less able to enjoy the party. What a nightmare!


    Very simple>>>>> My bras stripe broke and my whole front (if you know what I mean!!) was upsided….. in other words not lined up on bith side equally!!!…oops and I was at a all day meeting and activities, no safety pins around!!


  25. My worst oops bra moment was at my 10 yr High School Reunion. The worst part is….I didn’t really know it until I saw pictures taken at the event. After seeing them, I was mortified! I had a black sweater that must have had little micro holes in it, that I never really noticed before. I wore a wife push up bra underneath. I thought it looked good, but apparently, the white bra showed through the sweater in every picture. Ugh! No one said a word to me…including my husband!

  26. I had a personal trainer -who I thought was pretty attractive- and my bra had been chewed on by my new puppy the night before. But I figured it would last through my workout.
    Well right in the middle it snapped and basically exploded in the front (front clasp) and the girls were hanging loose.
    With a look of shock on both my and my trainers face we realized what happened.
    I had to ask him to get me a safety pin so we could continue my workout. But in order for him to find a safety pin, he had to ask like every guy in the gym where they kept them. But of course he had to explain to them WHY he needed a safety pin.
    I wore a sports bra every day after that.

  27. My biggest oops bra moment was when I wore a strapless bra to a highschool dance and ended up with it down at my waist! I looked like I had 4 breasts, not flattering.

  28. Erika Elizabeth

    In a rush to get ready to go out, I borrowed a strapless bra from my friend to wear the halter I had brought along. Not until I was AT the bar staring in the mirror did I realize it made my breasts as pointy as party hats. I felt like Madonna in the 80s claiming to be VOGUE. And it wouldn’t be better to let my breasts go WITHOUT the bra since my Ds would be low-riding.

  29. Worst bra moment–the time an elderly nurse saw me in my bra and jeans in the doctor’s examining room and I was only 11. For some reason, my first bra had little animals dancing over the cups. The nurse exclaimed loudly enough for all the other patients in the examining rooms to hear: “Oh, how cute! A training bra!” I guess a training bra is to train the girls which way to grow.

  30. allyson ayala

    i am on the smaller side, if i don’t wear the right bra i look llike am a teenager

  31. my worst bra experience was on a first date in hs. We were playing putt-putt and my front snap bra came completely undone and my tight, white shirt left nothing to the imagination.

  32. Jillian Veit

    One time my bra strap came undone while on a date….I had to sneak off to the bathroom to re-arrange myself

  33. Samantha Miller

    I have bras where the straps can be moved to be a strapless and etc. I was wearing a tank top one day and the back strap kept coming undone and it was impossible to put it back by myself. I had to keep asking friends to fix my bra. I eventually just took both straps off and put them in my purse and went strapless.

  34. My daughter was four months old and I had taken her with me to get take out for my husband’s birthday. We were waiting for our food when the hostess came over and tapped me on the shoulder to say that my breastfeeding was making restaurant goers uncomfortable. I wasn’t breastfeeding, I was standing waiting for food. Confused I looked down and noticed that my daughter’s foot had unbuttoned my shirt and pulled the corner of the nursing bra cover down giving a bit of a show. I was mortified!

  35. I was giving a presentation to a group of about 50 people at work — not a part of my job, but something I was asked to do at the last moment. I reached up to adjust the screen for the overheads and the hook on my front-closure bra popped apart. It was noticeable, as my chest is not small, and it is not firm. There was an audible gasp from the entire audience, then silence and not a person looked at me. I had no idea what to do. Pretend nothing had happened? Excuse myself? I picked up a binder and gave the presentation hiding behind it.

  36. mitchell b

    While at work one afternoon my bosses and I were deciding where to hang a new sign and it’s approx. measurements. As I went to move closer to the wall so did one of my female bosses, we bumped and I went to brace her inadvertently getting a feel of not one, but both of her breasts ! Very imbarrassing for both of us. We still haven’t spoken of it-ever !

  37. Years ago I used to ride and show horses. I was in the middle of a jumper class when ONE bra strap broke. I had one boob firmly in place and the other one flopping around, fortunately hidden under my jacket but they are 38Ds. Not much you can to to hide a happy free boobie.

    Bonus bra oops: One day I slid off a horse and my underwire got caught in the horn. At that exact moment, the horse decided to spook, effectively ripping my bra and tank top off and leaving me topless in front of a dozen people.

  38. I was giving a lecture to a group of college students. I turned around to lower the screen & “pop!” Yes, a strap broke. Someone said, “What was that?” The response was only giggles. Well, I finished the lecture with 1 36DD “hanging low.”

  39. Nancy Kavorkan

    A local newspaper published a photo of me at a charity fundraising event. I was wearing a pink chiffon dress with a beige bra underneath. The camera clearly captured both of my nipples as if I was braless. The news article was front and center displaying two fleshy mounds and nipples. I was too mortified to answer my phone for days.

  40. Kathy Scott

    I am over weight so the perfect bra helps hide a little of the problem.

  41. Ooh this is tough! I guess my worst bra-related moment was when I was younger, I was really into bras with cute prints on them. I had this shocking yellow Joe Boxer bra with little smiley faces all over it that I wore all the time. Well, 1 day in the summer, there was a random thunderstorm in the afternoon and I was stuck outside at the park with my friends, in a white tee and the bright yellow smiley-face bra. I bet you can guess what happened… but I swear you could not see the bra through the shirt before it got soaked lol!

  42. My biggest opps was having a strap break and having to try and tie it back together because there were no safety pins or needles or anything even remotely useful.

  43. I’ve had my nursing pads fall out of my bra on occasion while out and about.. very embarrassing!

  44. Heather C

    I was planning a big meeting with the big boss on an Air Force base. Since I was running things, I had to be in front, running the slides, dimming and bringing up the lights, etc. Well, I chose that day to wear the one bra where the underwires had a habit of poking out…and stabbing my poor boobs. Both wires would stick me, and I’d just have to sit there like nothing was wrong for hours!

  45. CONTEST CLOSED! Winner will be announced soon. Thanks for sharing your stories! 🙂