Dressing The Boyfriend

If he's not preppy, I'm not interested.

I used that litmus test over and over again when I was single and dating. I never would have met my long-term boyfriend, Ben, if his Craigslist personal ad didn't include that most important keyword: preppy.

When we met, Ben was a 22-year-old from California who described himself as preppy. But he was only grasping for the concept of prep style. He shopped at Abercrombie, Old Navy, and Hollister (not my idea of preppy). He wore baseball caps backwards. He popped his collar. He wore flip flops a lot. He owned a blue blazer. As my real estate broker might say, Ben was a fixer-upper with potential.

Fortunately our personalities clicked. Ben admired my taste in clothing and was willing for me to help him dress better. I'm a bit of a control freak, so I suggested that Ben let me decide what he should wear on a daily basis. Ben tends to be passive and I wasn't surprised when he agreed.

Given a green light, I jumped into action. I wanted to dump Ben's entire wardrobe right away and start from scratch, but our budget necessitated upgrading a little at a time. I had to prioritize. My first task was to eliminate the baggy and frayed clothes Ben liked to wear after work and on weekends. I wanted him dressed neatly at all times. All of Ben's cargo shorts, blue jeans, and oversized shirts went to Goodwill. I replaced them with Bermuda shorts, chinos, fitted polo shirts and Oxford cloth button downs. I also got Ben a pair of penny loafers. That was a good start.

After four years, most of Ben's old clothes are gone. I continue to upgrade Ben's wardrobe and, in general, he's cooperative and appreciates my guidance. It is interesting to observe Ben's reaction the moment he opens a package I've brought him from the store. A cheerful expression is most gratifying for me. When his expression is doubtful I am satisfied knowing that I'm pushing Ben's boundaries; it means we're making progress. Occasionally, Ben resists one of my ideas (pink Oxford cloth shorts, for example) but I always manage to coax him along.

Ben's new wardrobe is ultra preppy, like mine. At this point I think Ben could choose his own clothes, but I like dressing him up and I plan to continue doing it. To be honest, this is not only for Ben but also for myself. What he wears reflects on me. A well dressed boyfriend is the best fashion accessory.