One-of-a-kind gifts can make holiday shopping feel thoughtful again. Each item has a story and a personality of its own–which makes it easier to match the right gift to the right person.

The Criteria team and I got together last weekend to make a curated vintage gift guide inspired by some of the things we currently have in the shop. Every category reflects someone we know, love, or shop for regularly.

From the commuter braving the windy city streets, to the showstopper who treats every outing like an event, there’s something here for every vibe. 

1. The Commuter

Someone who is constantly on the go needs pieces that are stylish and functional. From subway platforms to windy street corners, they rely on outerwear and everyday staples that work hard, stay warm, and look good while doing it. 

Perfect pairings - warm coats, turtlenecks, crossbody bags, durable boots.

  2. The Nostalgia Lover 

Someone who lights up at everything that reminds them of back then–old school details, familiar colors, and pieces that instantly transport them to their favorite era. 

Perfect pairings - items that feel like childhood but updated for today: 90s sunglasses, mini purses, charms.

3. The Minimalist

Their motto is “less is more”, and their wardrobe reflects the no-drama mindset they’ll be bringing into this holiday season. A handful of thoughtful, high-quality pieces brings them more joy than a closet full of clutter.

Perfect pairings - Something they’ll gravitate to almost daily: designer belt, versatile bag, or even a gift card so they can pick the perfect piece.

4. The Maximalist

Give a gift (or two) to that person who never misses a chance to express themselves. Their secret? The more, the merrier: layers, dimensional textures, bold silhouettes, vibrant colors, and funky patterns that spark conversations.

Perfect pairings - Colorful scarves on bags, kitschy charms on bracelets, chunky belts on pants

5. The Office Dweller

Someone who stays on trend after the 9 to 5 ends. Their polished wardrobe – with just a touch of nostalgia – proves they are a true lover of timeless style who nails “dress to impress,”whether they’re in a meeting or at happy hour. 

Perfect pairings - Pinstripe pants, fitted button-downs, structured skirts, pearl accents


6. The Showstopper

Someone who considers every moment “the moment” deserves vintage pieces that shine as bright as their sparkling personality. For the friend who lights up a room, and inspires everyone around them, bold vintage is a must. Warning: Jaws will drop and heads will turn. 

Perfect pairings - Glitter tops, fringe coats, power pants, colorful shades

7. The Party Animal

Their day starts after the sun sets, and their best looks come alive under the neon lights. Every night is like New Year’s Eve, from tucking into cabs to grooving on the dance floor, their feisty fit is always cause for celebration.

Perfect pairings - Tall boots, mini purses, fur coats, animal print 

8. The Dark Academic

Their love language? Effortless layers built for long hours reading poetry at their neighborhood cafe. Their style is moody, cozy and intellectual–with enough depth to match their favorite dog-eared novels.

Perfect pairings - Corduroy pants, turtleneck sweaters, plaid blazers, wool trenches, long scarves, loafers

9. The Rebel

For the loved one who tears through life at fast speeds, and looks impossibly cool while doing it. They gravitate toward lived-in denim, tough leather, and pieces that tell a good story.

Perfect pairings - Leather jackets/vests/gloves, distressed denim, Harley tees, bandanas, silver chains

10. The Cozy Curator

Someone who thrives in soft textures and slow moments. Their style is timeless and comforting–perfect for tea on the couch, yet still effortlessly chic in that “I just threw this on” way. 

Perfect pairings: Trusty trousers, loafers, knit cardigans 

11. The Sporty One

Whether they are cheering from the sidelines, or still playing on the weekends, sports are part of their identity.Their style nods to team pride and classic athletic design.

Perfect pairings: vintage team wear, sports themed accessories, tennis skirts

12. The Hipster

For the urban explorer who spends afternoons wandering flea markets and evenings sampling local brews. They are effortlessly cool, subtly nostalgic, and chasing adventure has never looked so easy.

Perfect pairings: Flannel shirts, boots made for walking


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Vintage isn’t about buying more–it’s about buying better. When a piece is truly one-of-one it carries intention, personality, and a story worth passing on.

From all of us at Criteria--Thank you for shopping small and thoughtful this holiday season!

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A big shoutout to Veronica Cook for contributing to this article!