Know Your Local Thrift Store (and Love It)
Some of your best deals are going to come from thrift stores, consignment shops, and similar second-hand markets. The selection is a craps shoot, but the prices are good enough to justify the extra time that costs you. Get in the habit of visiting your local thrift store (or stores) whenever you happen to pass by. If you never happen to, make a point of doing it every month or two anyway. The results will be varied. Depending on your body type and size, you may have a wide selection that gets picked over quickly, a limited selection that no one’s competing for, or something somewhere in between.
E-thrift — But Cautiously
The internet is, in some ways, a thrift store the size of the world. If you’re good at Googling and willing to put some time into it, you can find almost anything for cheap. Unfortunately, there’s no way to try clothes on via the internet. You’re stuck relying on product descriptions, which can be incomplete or even falsified. And there’s no way of knowing for sure until the purchase arrives on your doorstep. That means being a little cautious when you buy second-hand clothes online. Try to stick to websites that you trust or sellers with good reviews and reputations. See what other people are saying about a source before using it for the first time.
Track Sales and Coupons
Coupon-clipping is generally associated with grocery stores, but it’s an option for clothing shoppers as well. These days, you can use websites to track sales and special offers from brands you like. Sites like Dappered.com exist to highlight the best deals available every day. You should also subscribe to the mailing lists of the brands or stores you like best. This will inevitably result in some offers you aren’t interested in, but it’ll also expose you to some deals you do want. Deleting an extra e-mail or two each day isn’t that big of a hassle. And it’s well worth the effort when you’re also occasionally getting significant discounts on items you were going to purchase anyway — or that you wanted to buy but couldn’t because of the price.
Ask for Clothing Gifts
Take advantage of gift-giving holidays like Christmas to get the word out that you’re into fine menswear these days. Relatives and friends are often grateful for a few gift ideas that you’ll appreciate so that they’re not guessing completely blind. Of course, you’re not likely to have many friends who are giving away custom-tailored suits (though if you do, you should stay friends with them!), but you can let it be known that affordable accent pieces like pocket squares, colored socks, and vintage or artistic belt buckles are right up your alley.
Borrow from Relatives
If there are other men in your family about your size, check with them about borrowing clothes when you need them or about getting some hand-me-downs. This is usually a father-son sort of thing, but brothers, cousins, and nephews/uncles can help each other out too, so long as they’re about the same size. Go with whatever arrangement comes naturally to your family. Borrow a suit for an interview if you don’t have one of your own, maybe, or take a vintage suit jacket that’s seen better days out of mothballs and wear it with jeans or corduroys as a funky sports jacket.
Spend More, Less Frequently
Try to get into the mindset of investing in two or three serious clothing purchases each year and not much beyond that. (If you’ve got the budget for more frequent purchases, of course, go for it. But men who need to save for a few months between clothing investments should focus on two or three a year.) Make these significant, high-quality purchases. Focus on the upgrades that will do your wardrobe the most good, and spend to get the best quality you can afford. Buying one or two perfect items that are built to last will do you better in the long term than shopping every week or two for cheap junk. Your wardrobe will be a little less varied, but you’ll get more value for your dollar.
Adjustments Are Always Worth It
Finally, if you’re doing a lot of second-hand shopping, remember that adjustments at tailors are always worth it. Always. Spend the $10-20 per piece to get your wardrobe fitted to your body. Some adjustments will be minimal and cheap, while others will be more costly, but all of them are worth the extra investment. It’s the difference between wearing second-hand clothing and looking like you’re wearing second-hand clothing. Once the garments have been adjusted (and repaired, if needed), there’s nothing to make people think they’re anything less than the season’s newest looks, hot off the shelves.
Try not to get hung up on the idea of “slimming down.” The goal is to look good, not look like you have a different body. Simple solids, dark colors, and a clean silhouette all go a long way toward making a broad man look big and powerful rather than out of shape.