My Crazy Life—Working as a HighSchooler at Sears’ Ladies’ Lingerie Department

My Crazy Life—Working as a HighSchooler at Sears’ Ladies’ Lingerie Department

When I first decided to preach the “Gospels of a Gentleman”, I was not the master orator that I am today, but none of the world’s greatest preachers were great right out of the gate, including the late Reverend Billy Graham. For me, my path to becoming a Gentleman began as a result of applying to work at Sears, and my subsequent placement in the lingerie section.

All roads lead to Sears, but few start with a man purse.

In the summer of 2008, I applied to work at Sears after a summer spent working at Dairy Queen.  On the day of my interview, I showed up the same way that I had dressed for school – very stylish.  I walked into that interview wearing a slim fit shirt, slim fit jeans, and a pair of black Nike Air Force 1s with a gold swoosh, but also with a man purse around my waist.  Although the interview went well, the managers were caught off-guard by my swag.  They probably assumed that I was going to change clothes before the interview, but clothes do not make this man.  At the end of the interview, I was told that I had the job, but also that I was never to show up for work dressed how I had showed up to that interview, and how Sears’ dress code was dress shirt, dress pants, and dress shoes.

I truly believe that my man purse helped me get that job because of how much it helped me in other situations.  Although man purses are not that unusual now, back in 2008, all the insecure guys my age would try to diss my “euro trash” swag with ‘manly’ jokes.  Little did they know that all the girls that they had crushes on, or their girlfriends, were into the man purse as much as they were into me—a chick magnet.

Start with Ladies’ Shoes, End with Ladies’ Lingerie

My first day on the job was a Saturday morning, and I was assigned to job shadow a female co-worker at the ladies’ footwear cash.  I was told that I would only be helping ring through transactions, but I happened to ask the first customer I interacted with if they would like to take advantage of our customer loyalty program by signing up for one of our credit cards.  Their answer was yes.  I would get two more “yesses” before my shift was over.  The hiring managers were thrilled, and they told me that prior to my arrival, nobody at that cash had managed to sign up a customer in over two weeks.  It was the single greatest rookie debut in the history of Sears, and after a few more weeks at the ladies’ footwear cash, I was transferred to the lower main cash, the busiest of them all and right next to the ladies’ lingerie department.

At the lower main cash, I continued to do more of what I did at the ladies’ footwear cash, helping customers take advantage of our loyalty program, but I would be lying if I said that I was comfortable with handling all the lingerie that came my way.  Sometimes the lingerie came packaged in a box and other times it would be on a hanger.  When it came in a box, I had to open the box and authenticate the contents of that box, making sure that it was the same brand and size listed on the box.  When it came on a hanger, I would have to unclip it, fold it up and wrap it in tissue before bagging it.  Best of all, after ringing their items through the register, I would have to ask about their lingerie shopping experience.

What I never imagined was the responses that I would garner from our female shoppers, where they would say things like, “Which one do you think looks better on me?” and “If you were seeing me tonight, which one of these would you prefer that I wear?” On one occasion, one of the regular customers came to me with two different night gowns.  She asked which one I thought would accentuate her body more.

By this time, I had become a ladies’ lingerie professional, and I responded to her like a true gentleman, by saying, “Well, it really depends on what you are planning to wear underneath.”

She laughed voraciously and with such glee, that is, until she saw that there were other women standing behind her, and her whole demeanor changed.  She gave me a “how dare you!”, before walking away, only to return after I had finished helping those other women and they had left, so that she could continue to chat me up.  If you are wondering why she changed her tune, please remember that the late 2000s were still a period of conservative societal values and “women supporting women” did not catch on until the late 2010s.

At this point, you might be asking yourself how the hell did anyone think it would be a good idea for a seventeen-year-old boy to handle ladies’ lingerie and to be asking women about their lingerie shopping experience. Looking back on that experience, some 15 years later, it becomes clear that I was used as “cougar bait” and unbeknownst to everyone, myself included, was the fact that I was a “cougar charmer”.  That part of my life certainly belongs in the multiverse of American Pie movies.  However, please do not go around calling me “Stifmeister”, but I will consent to being referred to as “gentleman Steve” since we both dress similarly and are floral connoisseurs!

In the late 2000s, social media influencers were not a thing and if anyone wanted to seek out advice, they had to browse through online discussion boards.  That is why I decided to take it upon myself to share all the knowledge I acquired about ladies’ lingerie at Sears with other kids my age, kids who were on pace to turn out like Andy Stitzer from the 2005 film “The 40-Year-Old Virgin”.   Thus began the Gospels of a Gentleman.

For now though, what I can share with you is an additional story about how I also became a Sears’ sheriff and profited immensely from people that tried to steal from our glorious department store, but also how the store chose to prioritize the wants of benchwarmers over a generational talent.  A tale of injustice and, naturally, triumph, but one that will have to wait until next time.