As much as we love swapping tips and tricks to solve our biggest fashion and beauty dilemmas, there are some questions we may not feel comfortable asking our friends about, let alone Google without going incognito. Don’t worry. We’ve got you covered. In this series, we’re tackling those embarrassing queries by turning to experts in the field to get you the answers you need — minus any awkward feelings.

For most of us, the idea of spending a whole paycheck on anything (other than maybe rent) is daunting. Now imagine taking that amount, multiplying it by 2 (or even 10), and using it toward a handbag. We know... the prospect of making a stylish splurge like this may seem totally unrealistic. Even if you've been working your butt off and are financially ready to pull the trigger (you go, girl!) there are still so many factors to consider. In this installment, we explore the sometimes embarrassing, often puzzling, and always relevant questions (and answers) about shopping for designer handbags.

SHOULD I INVEST IN A HANDBAG?

Whether you're spending $10,000 (or much more) on an Hermès Birkin or opting for a $300 Rebecca Minkoff crossbody lewk, a good purse is the icing on our sartorial cake. "A handbag is the ultimate accessory. It can elevate your look effortlessly, it always fits, and it’s also practical since it holds all of your most important items," says Mandi Meng, VP of Marketing and Communications at What Goes Around Comes Around (WGACA), a company that specializes in the resale of pre-owned, designer goods. When considering whether or not to take the high-fashion handbag plunge it's important to consider two main questions: Do you love it and will you use it? If you answered yes to both of these then it's time to pass go and *spend* $200 (or more).

SHOULD I BUY NEW OR VINTAGE?

In general, new bags are just like new cars — once you walk out of the store, they immediately begin to lose value. Although purchasing a fashionable freshie is always thrilling, it's often smarter to hunt for second-hand designer styles first. "Buying a used handbag is a great entry point into the luxury market for those who typically cannot afford full-price items," says Charles Gorra, founder and CEO at Rebag, an online marketplace for pre-owned designer handbags. "With used bags, they may either keep the value at which it was purchased or due to demand it could potentially increase." Although you shouldn't count on your vintage find appreciating in value, limited-edition collabs and rare or discontinued styles can often increase in value over time — even in vintage bags. So exactly which ones are both worth the splurge *and* will hold their value? According to Rebag, the best investment brands are Hermès, Chanel, Gucci, Louis Vuitton, and Fendi — in that order. Luxury brands hold their bags to high-quality standards, which means the materials and the craftsmanship is next level.

Hunting for vintage bags can also be a really exciting sport and is often the more affordable route for everyone — not just first-timers. "I love the thrill of finding a bag that is a great price and in great condition that is totally my style," says Zoey Washington, Brit + Co Senior Style Editor and the proud owner of a 40-piece designer bag collection. "I only buy consignment bags. I never pay the retail price [because] the markup is insane."

HOW DO I PICK A BRAND?

There are so many good bags out there at various price points that choosing the right brand and style can feel overwhelming. It's essential to decide whether you're looking for that signature silhouette to have and to hold forevs or something fabulous that's on trend right now. While we don't know exactly which bags will appreciate over time, we do know that the iconic brands will always be in style. Consider resale value, design, and overall versatility. How often will you wear it? Which designers are the most 'classic'? Which ones are more edgy and outlandish? "I go for Chanel and Céline bags above all others because I know that I can resell them if I ever needed to," says Washington. "I'm more of a casual basics kind of woman, so draping one of these numbers over my everyday clothes just makes me feel special."

If you're looking for a guaranteed investment piece, choosing from one of the above-mentioned labels is smart and almost like investing in fine art. "I tend to stick with the houses that have been doing this for a while," says Heather Whittenburg, fellow handbag collector, and former accessories editor at Marie Claire. "The attention to detail, especially with Hermès, can't be matched, there's a reason these bags are so much more expensive."

SO HOW MUCH IS *TOO* MUCH TO SPEND?

Deciding what's affordable is such a subjective decision — even when you work at a designer bag company, everyone has a limit. "Over $2,500 is too much for me," says Lalena Luba, vice president of public relations at Kate Spade New York. "And I’m probably not going to do it."

Generally speaking, if the amount in question puts you in credit card debt, causes you to be late on rent, or gives you anxiety and/or buyer's remorse, it's too much to spend. Consider putting the bag on layaway or setting some money aside each month in a special handbag savings account. Figure out what other things you can cut back on and be more mindful about daily impulse spending. "It depends on your budget," says Meng. "I don’t think anyone should bankrupt themselves, but I’ve definitely scrimped in other areas of my life over the years to purchase the perfect handbag."

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(Photos via Edward Berthelot/Getty and Christian Vierig/Getty; Illustrations by San Trieu)

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