Skip to main content
The M Dash

Live with purpose.

First Suit Stories: 11 Tales of Awkward Outfits

September 10, 2016 | Filed in: Your Closet

Remember the first suit you ever bought? Chances are, it was awkward, poorly-fitting, and sweat-inducing, but you wore it anyway, presumably to soldier through some stressful event like a job interview or a bat mitzvah. Well, cheers for getting through that! In the spirit of our new suiting, we’re highlighting eleven tales of first suits, collected from colleagues and peers.

The Suit That Went to Waste

When I was in college, my mom bought me a suit before my first big corporate internship. She had gotten her MBA in the ’80s and then worked as a consultant for McKinsey, so she knew suits and how to dress for corporations where one wanted to be taken seriously.

The suit she chose for me was composed of a silky blazer with a matching skirt and pants. I paired it with a bunch of no-iron button-ups, because I could not be trusted to dry clean or iron with any regularity. The skirt was pretty kicky, actually; it had pleats that gathered in the back like a little fishtail (it sounds uglier than it looked). The pants were long and meant to be worn with heels.

To this day, I have never held a job that required me to wear a suit. Including that internship.

Ann, Marketing Executive

The Suit That Served Me Quite Well, Thank You

I bought my first suit the summer after I graduated from college, even though I didn’t have any interviews lined up yet (I was an English and Creative Writing major, or, as my dad put it, “Had no prospects”). The suit was plain, black, and on sale from Club Monaco. It was rather baggy in the thighs and midsection, but what did I know? I first wore it to a job interview at a crappy trade magazine where I was asked if I could “handle being yelled at.” Then the interviewer caught his pants pocket on his chair and they ripped a little bit in the butt area, which was hilarious. I declined a second interview.

I wore it again a few months later, after I got a real job at a newspaper and was sent to interview Navy Seals on a missile cruiser docked in the Hudson. This remains the only time in my life that I’ve been grateful to own a suit—the officers were all incredibly formal, and it was super-windy on the ship, so a dress would have been disastrous. I haven’t needed a suit since, and I donated this one to Goodwill a few years go.

Charlotte, Writer

The Patriotic Old Navy Blazer

The summer after I finished sixth grade, I attended a “leadership journey” program in Washington, D.C. We spent most of our time riding in Greyhound buses along the National Mall, but more importantly, it was my first exposure to the realm of business casual attire.

Hailing from suburban Colorado, where Abercrombie logo shirts were the height of chic, I was ill-prepared for the buttoned-up, conservative environment of the nation’s capital. The program had a business casual dress code, and with my mother in tow, I set out to add some elevated pieces to my wardrobe.

Where does one go for business casual attire in middle school? Old Navy, of course! We spent the better part of an afternoon combing through clothing racks, and one of the gems I walked away with was a khaki button-up blazer. It was stiff, too long in the sleeves, and came with no matching pants or skirt. Still, never in my twelve years had I felt so polished. Paired with the long skirts and dress pants I also acquired that day, I felt myself to be the definition of a patriotic, dutiful citizen as I meticulously took notes at the American History Museum.

Alexa, Investment Banker

The Suit That Won’t Let Go (Literally. It Has Hooks on It.)

I bought my first suit in 2000 for my consulting and investment banking summer internship interviews. I had been waiting pretty much all my life to buy a suit (so professional!) and was beyond giddy to have a real reason to do so.

I instantly fell in love with a streamlined, elegant Banana Republic suit with very of-the-moment hook-and-eye closures in front (no buttons). I wore it for all my interviews (offers given at every one!), as well as throughout my consulting career. I haven’t worn it in maybe 10 years now, but I can’t seem to give it away.

—Jessica, Marketing Manager

The Freakout Suit

I bought my first (and only) suit in a complete panic. I was a few months into my first job at a communications consultancy. Our office was fairly casual, but many of our clients were more corporate, and after my first few meetings, I realized I needed to step up my game. With a big pitch meeting looming, I ran down to Soho after work, and after a frenzied search through the racks at Benetton (I have no idea why this was my store of choice), I ended up with the most hideous skirt suit you can imagine: muddy brown with an odd, satin-y sheen.

Why did I choose that particular suit? Easy: I am cheap and it was on sale (for good reason). I hated it from the very moment I bought it, and I only ended up wearing it once—years later—to an interview where I immediately realized I was egregiously overdressed. Oh, well.

Tory, Creative Director of Brand

The Bat Mitzvah Suit

My first suit was for my bat mitzvah. Needless to say, shopping for it was super awkward. Everything felt way too grown-up (which, duh—I was 12). We went to Talbots, Ann Taylor, Saks, everywhere. After trying on probably 20 options, I ended up with a burgundy tweed skirt suit. Of course, I also had to wear a pair of sensible heels, and they had to match the suit exactly. We bought closed-toe mules, and I put tape on the bottom because I was so scared of slipping on the synagogue carpet while I was carrying the Torah.

—Sharon, Software Developer

The “Flight Attendant at a Bat Mitzvah” Suit

I bought a black Theory skirt suit for my first job interview. After I was hired, my manager said, “Oh, yeah, get rid of that horrible outfit. You look like a flight attendant at a bat mitzvah,” and made fun of me for ages about it. I ignored him and kept it—I still have the blazer, but the bottom half hasn’t fit me in years.

—McKayla, Branding Consultant

The Suit That Convinced Me Otherwise

My mom is a powerhouse of a businesswoman; she has spent her career working in healthcare administration, and has two masters degrees. So I followed her advice when she said, “Everyone needs a good suit.” I was 16 and in high school, and we were shopping at Filene’s Basement (remember those?) when we came across a heather grey wool skirt suit from Jones New York. The skirt was midi length with a bell-shaped flare at the bottom and came with a classic single-button blazer. To my great fortune, this suit was in my size, and on sale! It fit well and joined my wardrobe.

I wound up pursuing a career in a creative industry, and I wore the blazer only once, ever. The skirt never saw the outside of my closet before being donated to someone with a less flexible work environment. My current take on the “suit” is the Soho skirt with a button-up top (partially tucked in, of course).

—Andrea, Product Designer

The Suit That Spoiled Me

I got my first suit the summer before eighth grade. The impetus for this purchase was my decision to join the high school debate team (yes, as a middle schooler), under the encouragement of my older brother and parents. I was visiting family in Shanghai at the time, which meant I had access to relatively inexpensive tailoring. Hence, my first suit was bespoke! It fit perfectly, as expected, just not for long, given that I was a young adolescent. I continued competing in debate and speech throughout high school, and I got a few more tailored suits and shirts during my summer trips to China. Sadly, prices for tailoring have gone up since then.

—Katherine, Customer Experience Representative

The Shimmer Suit

My first suit was a three-piece in silver with grey pinstripes, two sizes too large. My alter ego Shimmer’s first suit was the Foster pant and Graham kimono in sheer rib, both black, worn with a silver boot. Shimmer did it better.

Jonny, Quality Assurance Analyst

The Victor/Victoria Suit

I was a sophomore in college when the finance recruiting bubble descended upon all Harvard economics majors. Investment banks would host fancy presentations at the faculty club with fancy bankers eating equally fancy cheeses, and in order to partake in these events and network, you needed a suit (and, ideally, some pearls). Being a full scholarship student, I didn’t have either, and had no idea where to find them. One day, I went shopping with a male friend who needed a tux, and we landed in a thrift store in Cambridge that sold high-quality secondhand menswear. I randomly found a vintage wool blazer that was $50 and fit well enough. It was designed for males, so hit me towards the crotch, but knowing nothing about suiting, I thought it looked cool and “breezy.” I wore it to several events before realizing that my hodgepodge attempt at an outfit was not, in fact, acceptable.

—Katie, Head of Sales

Our new Power Play collection offers a modern take on classic suiting, with no muddy browns or hooks to be found. Shop it here

Shop (Non-Awkward) Suits

Share this post. We dare you.

Read on.

Back to Top

Questions about styling or sizing? Chat with one of our stylists.