We’ve talked a bit about that “I don’t belong here” feeling, and the best way to overcome it is to look like you belong there. The way to do that is simply to dress the part. After having made several dubious fashion choices in the past (including a cordury suit *shudder*), I’ve finally learned how to do it, and I’m going to tell you what I’ve learned.
For men, dressing the part often means putting on a suit. Buying a nice suit can get very expensive very quickly, especially if you’re going to go for old-school custom tailoring. But this can work to our advantage. See, buying a suit is a commitment; a good suit should be expected to last at least ten years. For this reason, men’s fashion changes very slowly; a suit you buy today should still look just as stylish and fashionable in 2023. Your end of the deal is that you’re promising not to gain or lose more than a couple of pounds for the next decade. Many men fail to keep their end of the bargain, and that’s good for us.
As I said, a good suit should avoid the extreme fashion excesses; if you find a suit cut on classic lines and in a subtle wool fabric, you shouldn’t be able to tell whether it was made in 1985 or just last week. That, combined with America’s obesity epidemic, means there are a lot of perfectly decent suits, some quite expensive, that their owners can’t wear anymore, and if you can find them, you can get them cheap. So where are they?
Go to the most expensive and snooty part of your town and find the nearest thrift store, ideally one that’s connected to a high-profile charity such as a hospital. Goodwill or the Amvets stores will do; you’re looking for the place where the very well-to-do dump their discards. In my area, I can choose from San Marino, La Cañada, or Arcadia, all very pricey neighborhoods. If I wanted to, I could drive down to Beverly Hills or Brentwood. You know where the rich live in your town, and you probably can guess at their pet charities. Go there.
When you find the store, look for a suit that doesn’t have any of the signs of past fashion trends; wide (or very skinny) lapels, pinched waist, big pleats in the pants, dated colors, etc.
Look for a conservative color, a nice grey or navy blue; if you’re only going to wear a suit a couple of times a year, don’t make it black unless you’re planning to hunt aliens or sing with Dan Aykroyd. If it’s a pinstripe, go for a subtle one with very thin stripes; you don’t want to look like an extra from a production of “Guys & Dolls.” For the same reason, you might think twice about a double-breasted jacket. Make sure it’s not too period looking, and make sure it fits properly. It’s really easy to look like you’re wearing David Byrne’s “Stop Making Sense” costume if the jacket is too big. Another area of excess is shoulder pads. Older suits, especially from the ’80s, will often have them. You can sometimes yank them out, but it’s better if they aren’t there in the first place.
Look inside the jacket for the manufacturer’s (or even better, tailor’s) label. If you find a name you recognize, like Brooks Brothers, Kenneth Cole, J. Crew or Armani (you should be so lucky), great. If you find a “custom tailored by ___” patch, that could be fantastic, but there are a few more things to look for, starting with the material; you can’t go wrong with wool (unless you’re allergic to it). Look at the inside of the waistband of the pants; you can tell at a glance if they’re hand-made, and how good a job they did. If the suit is hand-tailored, check it over carefully for split seams and loose threads. If you are handy with a needle, you can repair a lot of these, but it’s better to avoid them in the first place. Also look for stains, holes, snagged fabric, and worn spots that will eventually wear through.
Ideally the thrift store will have a changing room so you can try on your find. If not, at least try on the jacket. Make sure you have someone with you who will give you an honest appraisal of the fit. You can usually have the pants taken in or let out and the length adjusted, but jackets are a lot more work and cost more to do.
Here’s a really good guide to essential suits, published by Esquire (personally, I’d say skip the fourth one entirely unless you plan on wearing suits often, and please, for the love of Tim Gunn, choose something tasteful if you do go for a pattern; you don’t want to be Herb Tarlek); you can apply the principles without ponying up the $1300 they suggest. From the same site, here’s a critique of Banana Republic’s suit buying guide. These people really know what they’re talking about. If you pay attention to their advice on fit and style, then haunt the thrift stores, you’ll look sharp for a ridiculously low price. If you’re successful in your quest, you can go home with a great looking suit that will serve you for years, and you’ll probably spend around $20-30 for it. Now you are ready to, in the words of Barney Stinson, suit up.