The Pick: Snapshot Colorblock Small Camera Bag, $295, marcjacobs.com.
Why It's Worth the Splurge: There's nothing overtly trendy about Marc Jacobs' Snapshot bag—which means you can keep it in your outfit rotation for years and years—but it's definitely fun, thanks to the designer's knack for pairing unexpected colors and finishes. Prices start at $295 for color-blocked styles, including some with American flag-print straps, but there are also jewel-studded and glitter-finish versions in the $500 range.
The Pick: Soho Leather Mini Chain Bag, $850, saksfifthavenue.com.
Why It's Worth the Splurge: Even the tiniest Gucci bags are in the four-figure range, except for this guy, probably because it's more pared-down than most of creative director Alessandro Michele's embellished-to-the-hilt designs. It's hard to think of an outfit that the super-popular Soho bag wouldn't work with, and if you've fallen hard for it (but not for its price tag), you can always stalk resale sites like The Real Real, where we've seen them sell for a few hundred dollars less.