Do these cargo shorts make me look old?

Image from The Sartorialist. 

I work in fashion. That, perhaps, sounds a bit too glamorous. I don't send Supermodels down runways or have Diet Cokes with Isaac Mizrahi while discussing whether or not we think schiffli is appropriate for men to wear (Answer: I don't. Isaac, I believe, does.) But I do work in retail and have for the last 10 or so years.

I feel a certain need to be somewhat fashionable in the way that I dress. I figure, if I look like a slob, why would anyone trust my opinion about what clothes they should buy? I am however, pretty conservative in my sartorial choices. I am not our good friend Patrick, who told me the other day that his fashion aesthetic was "Shipwreck Chic." (Can't you picture it? Cut-off shorts, striped shirts, knit caps.) I want to look cool and relevant, but I also want to be age appropriate. Most of the people I work with are in their early 20s, so I am clearly the Grandpa of the store by a long shot. I can't wear the same things they do without looking like a dork.

A few weeks ago, I bought my first pair of skinny jeans. I feel like since that was the hip thing to do in 2007, it had now crossed the Rubicon into "acceptable for old people" category. I wore them and got compliments and liked them and I felt it was then OK to go and purchase these:

Image from Old Navy. 

Is this a bridge too far? Am I too old (or perhaps too young?) to wear slightly pink slim-cut khakis? They are in a box on their way to my house right now, so I'll let you know what the final verdict is.

There are a few rules I know and stick by that I feel like keep my clothing age appropriate. I reserve the right to change any of these rules (I remember telling my sister about 5 years ago that I would NEVER wear skinny jeans.) but I share them with you now. Perhaps you will find them helpful.

1. I don't wear cargo shorts. I don't think men who are older than 25 should ever wear cargo shorts (unless you are mowing the lawn.) Why do you need all those pockets? Did your house burn down and you have to carry everything you own? I am fine with shorts, but I try and get something with a better fit. Cargo shorts make you look like a frat boy.

2. I don't wear t-shirts and polo shorts and windbreakers that I got for free from work, or from a pharmaceutical rep, or from a soccer league that you were a part of in 1999 (Note: I was not in a soccer league in 1999 but you get the idea.) These are only acceptable for sleeping in or, again, mowing the lawn. (In my book, mowing the lawn is pretty much a free for all. You can wear hot pants and a fedora and it would be OK.)

3. I wear button up shirts as much as possible. (This requires ironing.) A button up shirt helps hide a gut, and that is a good thing. And I just look much more professional than the guy in the two-sizes-too-big "Syno-tech" polo.

4. I wear cardigans (or a blazer) whenever possible. A cardigan makes any outfit look better. Ironic tee shirt to work: too young. Ironic tee shirt under a cardigan to work: golden. If you don't own a cardy, why not? (Is it because I called it a cardy?) Come to my store and I will sell you one. Here is what I plan on wearing with the red pants:

Image from Old Navy. Is this, perhaps, too shipwreck chic?

5. Lately, I am trying to add more accessories.  Hats, tie clips, even a slightly hipster-ish scarf. Older people own accessories. Have you seen this guy:

He wears hats and is older and doesn't look like a kid. Also, he is really cool. 

I am not saying you need to follow these rules (although if you want to, feel free. Also, send me a small royalty.) Clothing should be about personal expression and feeling comfortable and looking good. You should wear what works for you and what works for me is trying to look like a professional 30-something guy in a casual environment. Maybe what works for you is wearing exclusively cargo shirts, free soccer-league t-shirts and baseball hats. Maybe what works for you (Patrick) is dressing like you are stranded on an island during a Vogue Uomo fashion shoot. And maybe it is wearing a white fur coat and white fur boots. Who am I to judge? It's not like I am Isaac Mizrahi.