Back in 2007
In 2007 this was the Dear Looks page, a gallery of outfit ideas.
Welcome to the Dear Lookbook, our moodboard of Y2K outfits built around one tiny, mighty piece: the heart-and-star baby tee. Think of it as a page torn out of a 2000s magazine, refreshed for now. Every look below is a formula you can recreate with what’s already in your closet, plus one sweet white micro-rib tee with a pink heart and a baby blue star (coming soon, join the waitlist at the bottom of this page).
Our one styling rule? Keep it playful, keep the proportions balanced, and wear two throwback pieces at a time, max. One baby tee plus one Y2K hero item looks like you. Six at once looks like a costume party (which is also fun, just a different plan).
How to use this Y2K lookbook
Each look has a vibe, the core pieces, and a little “make it yours” tip. Mix and match freely. If you’re not sure how a baby tee should fit before you start styling, read our baby tee sizing and fit guide first, then come back here for the fun part. For the full styling deep dive, see how to style a baby tee.
- Fitted on top, relaxed on the bottom is the easiest balance for a cropped tee.
- One color story per outfit: pink and baby blue, pink and white, or all pastel.
- Shine in small doses: a glossy lip, a rhinestone clip or a metallic bag is plenty.
Look 1: The Everyday Sweetheart
The baby tee with baggy or wide-leg jeans is the look you’ll wear on repeat. The fitted crop meets the waistband, the denim does the relaxing, and the heart-and-star print gets to be the star of the show.
- Heart-and-star baby tee
- Light-wash baggy or straight-leg jeans
- Chunky white sneakers
- Tiny shoulder bag worn high under the arm
Make it yours: add a thin skinny belt in pink or white to pull the colors together.
Look 2: Pleated Mini, Big Energy
For coffee dates, campus days and anything that calls for cute. A pleated mini skirt with a baby tee is peak 2000s, and it still feels fresh.
- Baby tee, tucked in at the front
- Pleated mini skirt in white, plaid or baby blue
- Knee-high or slouchy socks
- Mary janes or platform sneakers
Make it yours: swap socks for bare legs and ballet flats when it’s warm out.
Look 3: Cargo Cutie
Cargos bring the utility, the baby tee brings the sweetness. This mix of soft and sporty is one of the most searched Y2K outfit formulas for a reason.
- Baby tee
- Low-slung or mid-rise cargo pants (or a cargo mini)
- Chunky trainers
- Layered thin necklaces to keep it girly
Make it yours: a butterfly clip or two in your hair takes it straight to 2002.
Look 4: Layered Lace
The 2000s loved a layer. Pop a lace-trim cami under or over your tee, or let a thin strap peek out at the shoulder. Lace plus a heart print is pure sleepover-diary energy.
- Baby tee
- Lace-trim cami or slip layered underneath
- Flared or bootcut jeans
- Flip-flops or kitten-heel sandals
Make it yours: keep the lace in white or blush so the pink heart stays the focus. Not sure what a shrug or a cami is? Our Y2K glossary explains every term.
Look 5: Shrug It Off
A cropped shrug or tiny cardigan over a baby tee is the softest way to layer when there’s a chill in the air. It frames the print instead of hiding it.
- Baby tee
- Cropped knit shrug or bolero in baby blue
- Denim mini or a flowy midi skirt
- Ballet flats
Look 6: Pastel Track Day
Comfy can be cute. A zip track jacket or hoodie worn open over a baby tee is a lazy-day look that still feels put together.
- Baby tee
- Zip hoodie or track jacket, left open
- Matching joggers or flared track pants
- Sneakers and a claw clip
Make it yours: match the jacket to the star (baby blue) or the heart (pink).
Look 7: Weekend Denim on Denim
Double denim is a 2000s classic. The white baby tee breaks it up so the outfit never feels heavy.
- Baby tee
- Denim mini skirt or jeans
- Denim jacket tied at the waist or worn open
- Tinted sunglasses
Look 8: Night-Out Sparkle
Yes, a baby tee can go out. Tuck it into a satin skirt or sleek trousers and let the accessories do the glam.
- Baby tee, tucked
- Satin midi skirt or black straight trousers
- Strappy heels or platforms
- Rhinestone hair clips and a shiny mini bag
Make it yours: a glossy lip and a little shimmer on the cheeks, very 2000s.
Look 9: Polished Off-Duty
Tuck the tee into tailored wide-leg trousers and throw an oversized blazer on top. The playful print peeking out keeps it from feeling too serious.
- Baby tee
- Tailored wide-leg trousers
- Oversized blazer, worn open
- Loafers or pointed flats
Styling the baby tee by season
Spring and summer
Wear it on its own with shorts, denim minis, linen pants or sundress-style skirts. Light colors and bare arms are the whole point. Pack sunscreen.
Fall
Layer with shrugs, cardigans, a denim jacket or an open flannel. Jeans and cargos come back in.
Winter
Use the baby tee as a cute layer under a zip hoodie or over a fitted long-sleeve top, the way the 2000s did it. Add leg warmers or chunky boots.
Color pairings that always work
Our first tee is white with a pink heart and a baby blue star, so it plays nicely with almost everything. A few combos we love:
- Pink + baby blue: the full Dear color story.
- White + light denim: clean and classic.
- Pastel everything: lilac, mint, butter yellow.
- Black + pink: a little edgy, still sweet.
Lookbook FAQ
What do you wear with a baby tee?
Almost anything with a little volume or a high waist: baggy jeans, cargos, pleated or denim minis, flowy skirts and wide-leg trousers. The fitted, cropped tee balances out relaxed bottoms.
How do I make a Y2K outfit look modern?
Stick to one or two throwback pieces per outfit, choose good fabrics, and keep shoes simple. A baby tee with modern jeans and clean sneakers reads current, not costume.
Should a baby tee be tucked in?
It depends on the bottom. With high-waisted jeans or skirts, a front tuck or no tuck at all both work, since the hem usually lands near the waistband. With low-rise bottoms, wear it out for that classic cropped look.
Can I wear a baby tee if I don’t like showing my stomach?
Yes. Pair it with high-waisted bottoms so the hem meets the waistband, layer a cami underneath, or size up for a little extra length. Our sizing guide covers how length works.
Is the Dear baby tee available yet?
Not yet. It’s coming soon, and waitlist members will hear first. Check Drop News for updates and the FAQ for everything else.
More from Dear
Want the full story behind the name? Visit our About page and read about the original Dear line from 2007–2008. Want first looks and members-only extras? Join the Dear Club. For more style notes, head to the Dear Journal.
Join the Dear waitlist ♡
Be first to know when the heart-and-star baby tee drops. Pop your email in below and we’ll send a sweet little note the moment it’s ready.