Us, too. Hate all the legwork involved? Oh, yeah. Let’s face it, sometimes the thrill of the hunt can be less than thrilling when you find yourself empty handed. Between digging through overcrowded racks at thrift stores, driving from yard sale to yard sale, and wondering where all those secret estate sales are going down, successful secondhand shopping can be exhausting. That’s why we’ve teamed up with some of Chicago’s top vintage vendors and asked them for suggestions to help you shop like an expert. With the advice of these seasoned vets you’ll be well on your way to building an arsenal of one-of-a-kind finds. Who's the pro now? 
Shanti Clark, owner of Very Best Vintage
What are your favorite spots to score great vintage finds?
"After being in the vintage business for so many years, I’ve found that the really great stuff sort of finds me, rather than the other way around. My store, Very Best Vintage, offers consignment, buys, and trades, which brings in a lot of stellar items, often unique and in great condition. That said, I still love shopping for myself at other vintage stores. You just never know what you’ll find! One tip I would absolutely offer to vintage newbies is that they should subscribe to EstateSales.net. It’s an invaluable resource because items in the best condition are always the gems stowed away in a closet for a few (possibly several) decades."
What are your personal vintage shopping guidelines?
"It’s easy to get caught up in the moment. When I shop for myself, I try to only buy things that are comfortable and fit well. They’re simple rules, but it’s deceptively easy to be tempted to break them because of a beautiful fabric or something that almost fits...if only the entire dress were reconstructed. Small alterations are worth it if you love the garment, but you have to be realistic or you’ll end up with a pile of clothes for the tailor and nothing to actually wear.
A personal fashion rule that I follow pretty closely (in vintage and shopping in general) is to buy timeless pieces that don’t drastically change the body silhouette. I’m talking about shoulder pads and harem pants here. They can be fun and trendy, but are unlikely to be a solid wardrobe investment. I also always stay true to the things I know I love and will always wear. For example, I adore 1960s nighties. I think they’re really fun and sexy, and have a big collection at home. A lot of my regular customers already know about my preoccupation with vintage sleepwear because there’s always a substantial collection at the store."
Any words of advice for those new to vintage shopping? "If you see something you love, buy it! You’ll almost certainly never find it again. I’d also remind everyone buying vintage that many of these pieces are at least 20- years-old. You’ll likely find a flaw if you look hard enough. Seams will come undone, buttons will fall off, but the maintenance on a vintage garment is absolutely worth it because you have the privilege of wearing–and showing off–a unique and amazing piece of history."
Tell us about your favorite vintage shopping experience.
"I saw this perfect tiny champagne bucket charm with a tiny bottle emerging from a tiny mountain of jeweled ice. It was so charming and perfect and I really wanted to wear it as a necklace pendant. I was weeks away from a once-in-a-lifetime trip to Japan, so I chose to save my cash for the trip and forget about the charm. Because of the collectability (and because it was perfect!), some other lucky charm collector scooped it up after I passed on it before my trip. The trip was amazing, but lo and behold, months go by and I was still thinking about the champagne charm. It took me five years, but I eventually found that particular charm for sale and I bought it immediately! It’s still one of my favorite pieces and was absolutely worth the chase."
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