Mens Shorts, Button Up Wins Best Meet-the-Parents Outfit

There are three momentous occasions in which we prepare, more meticulously than ever, our most flattering and appropriate outfits. On the first day of school we select newly purchased pieces that will help us jive with the crowd of our choosing. For every job interview, we rummage through big brother or big sister’s, or our own business casual wardrobe. And for the first time we are meeting any significant person, whether it be a first-date or intimidating introduction to the folks, we thoughtfully design an ensemble that will best represent, and, dare I say, sell ourselves to the people we are trying to impress.

This, ladies and gentlemen, is where my expertise serves the most useful.

When one of my style-savvy friends solicited my help in choosing an outfit for an upcoming occasion, I knew it just had to be one of the three. Jackson is, for lack of a better word, a diva. His style is impeccable and his everyday-wear puts mine to shame. When styling for an elegant evening out, Jackson is the god of formal garb. But shockingly enough, the label-lover lacks in casual clothes, which is where I stepped in.

When Jackson’s boyfriend of six months launched the “I want you to meet my parents” missile, Jackson’s preparation for a parent-worthy outfit began. Since meeting your significant other’s parents is without a doubt the most nerve-racking point in any relationship (bar marriage proposals) Jackson was determined to select a look to wow.

The venue: The Harbor View Bar. The time and date: Late July, 5 p.m.

After hunting through some of Jackson’s overbearing collection of crisply pressed Thomas Pink button-ups and perfectly tailored suits, I decided the best strategy was to march right down to the nearest department store and do some in-store styling. 

For a casual venue and a comfortable fit, a simple J. Crew Slim Non Iron Dress Shirt and a pair of men’s shorts. By keeping the colors subtle and summer-appropriate, Jackson’s look exuded a confident, and down-to-earth personality guaranteed to woo parents.

Needless to say, the date couldn’t have gone better. As the potential in-laws feel in love with Jackson, I fell even more in love with my fabulously fashionable job, and carved yet another notch on my stylist belt for a deliciously dressed male client. 

For any man facing a clothing dilemma in one of these momentous occasions, follow my foolproof steps in becoming a stylish stud.