When was your first “Million Bucks Moment?” | Men’s Style

When was your first “Million Bucks Moment?” | Men’s Style

Tell me if you can: When was your first “Million Bucks Moment?”

I’m talking about the first time you got dressed in an outfit that made you let out a low whistle in the full-length mirror when you saw yourself head-to-toe.

The look that triggered an extended round of finger guns at your reflection.

Maybe it was that first suit out of college you bought yourself with your first real paycheck?

Or the midnight blue tux with the peak lapels you splurged on for your wedding—the one that had you saying, “Bond, James Bond” all night (much to your new bride’s exasperation).

Maybe it was simply a perfectly-broken in pair of blue jeans evoking Bruce Springsteen, circa “Born in the USA” and a beautifully faded button-down.

{Paul Rudd’s I Love You, Man, midnight blue tux-induced MBM}

I hope by now everyone’s had a Million Bucks Moment—or MBM, from here on out.

And if you haven’t? Well, you deserve one.

For me, my first MBM came in high school.

As a junior, I was asked to prom by Raj, a very handsome senior, who’s a doctor now…I don’t know why I felt the need to tell you that part, it’s really not pertinent to the story…


This was a very big deal for a fifteen-year-old who’d only just gotten her braces off a year earlier and for whom puberty had yet to set in.

Truth bomb I’m about to drop on you, so get ready:

Wisconsin is not the fashion mecca you might think it is.

For most girls in my school, formalwear began and ended at frosted pastel, sparkly princess dresses.

Even then, I was totally grossed out by the idea of wearing what everyone else was wearing just because everyone else was wearing it.

Instead, I took a cue from Sharon Stone at the Oscars a few years earlier. An awkward teen in the dairy state taking fashion advice from the leg-swinging vixen from Basic Instinct? It’s innocent, I promise.

sharon stone oscars, sharon stone gap, sharon stone men's shirt
{hard to tell, but I’m on the left}

The look? What she told reporters was her husband’s white dress shirt, paired with a long satin skirt in lavender.

It was the most gorgeous thing I’d ever seen.

Looking back, I recognize that even that young, I was already into the mix of the masculine and feminine when it comes to my personal style, though I’m sure the attraction to a look like this probably wasn’t conscious then!

So off I trucked to Marshall Fields, the nicest department store in town.

It’s a Macy’s now, which is fine, I guess, but Marshall Field’s was like, classy. Classy like a symphony. Classy like a monocle.

There, I found a Ralph Lauren floor-sweeping silk skirt in pink, and paired it with a white dress shirt from my mom’s closet that I tied up at the waist (hey, if you can’t take advantage of a flat midriff as a teenager who doesn’t yet have to work for it, when can you?).

Honestly I’m the last person to talk myself up, but I. Looked. Fantastic.

I looked like a million bucks!

Total MBM moment.

When Raj saw me, that low whistle mentioned earlier escaped his lips when he saw me…not a move endorsed by my parents, standing nearby and worrying for my teenage virtue. 

They really had nothing to worry about. I ditched Raj pretty soon after he’d thrown back enough wine coolers for the both of us at the after party in a friend’s conveniently-out-of-town parents’ basement.

Which was fine by me. 

Because I wasn’t busy worrying about how I looked, or feeling insecure that others looked better than me, I had a great night.

No forbidden wine coolers required.

abercrombie patterned cardigan
Does your MBM involve a trendy cardigan, like this Abercrombie style?

This experience fits my theory about why women have these “million bucks moments” earlier than men do.

It’s because while women’s first experiences of dressing up for a school dance leaves us feeling like a princess (or, in my case, Sharon Stone), you guys feel like a frog.

You’re renting awful-fitting tuxes with technicolor vests, three inches of pooled cuffs, a clip-on bow tie.

Who could feel good in a getup like that?!

So it makes sense.

You think, Dressing up is not a path to confidence for me. Why bother caring about clothes?

Cut to: way later – like much, much later – when you guys finally begin to invest in your appearance.

corduroy deck pants
Would this J.Crew look feel like a MBM to you?

For plenty of guys, that first MBM comes not in your teen years, but in your twenties—when you start having more money to spend on your clothes, when there’s a reason to spend more money on your clothes.

Some guys, though, are still waiting on their first Million Bucks Moment!

Whether from fear of judgment, or a lifestyle they’re convinced doesn’t require a grown-up wardrobe.

Some guys just never put in the work of upgrading their style game.

For these guys, that MBM is still out of reach.

Which is a goddamn shame, and a big reason I feel so strongly that what we do here matters.

When you look good, you feel good, and that confidence impacts every part of your day…and life!

I really believe the lack of “Million Bucks Moments” contributes to the lackadaisical attitude so many men take towards their personal style.

Because once you have yours, you don’t go back.

Once you know how good you can look, you don’t want to look anything but.

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