More Thoughts on Fall Fashion

A few weeks ago I went to the Gap to buy this pair of wool shorts that caught my eye on the website. They reminded me of a pair I wore back in the early 90s, also from the Gap. They were promoted on the website as wear-to-work shorts and pictured on the model, they looked preppy and conservative. In the store though, they seemed considerably shorter. “I just don’t think I can wear these’” I regretfully told the plucky young sales dude. “With some dark tights and boots they won’t seem so short,” he assured me. Not yet convinced, I left the store empty handed, promising to think about it. Think about it, I did, and a few days later I went back to buy them.

Yesterday I put them on for the first time since the Gap fitting room. “How do these look?” I asked Jeremy. He paused, searching for a diplomatic answer, well aware that such inquiries are relationship land mines. He countered my question with another question. “Would you wear a skirt that short?” Point taken. I changed into a knee length dress and went to work

Still determined to make them work, I solved the length problem by letting the cuff down. That gives me another inch and a half of fabric making them at least, office appropriate. I’m wearing them today with a cream button down top, brown tights and brown riding boots. I suppose I look a little silly but I still love these shorts. The outfit is very east coast retro, and makes me think of Alison Bradbury in The Sure Thing. If you’re not familiar with this reference, I recommend you go out and rent it. It’s one of the great John Cusack movies of the 1980s. An underated classic.

How adorable is circa 1985 John Cusack?

Ok then…getting back to the shorts. There are a few lessons to be learned here. For online shoppers, if you’re planning to order a pair of these for yourself, be aware that they’re shorter than they appear. For me, it’s yet another reminder that I’m now well into my 30s and look like an ass trying to wear the kind of clothes I wore in my late teens and early 20s. I’m still going to try though.

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