Tricky Story: Story 2 Level 27 Walkthroughs & Guide
Help Riley and Maddie choose the perfect outfits for the party
Help Riley and Maddie find outfits that match their styles for tonight’s party

Tricky Story: Story 2 Level 27 — Help Riley and Maddie choose the perfect outfits for the party Guide Overview
Getting Riley and Maddie ready for that party took me more tries than I'd like to admit. The outfit choices seem straightforward, but Tricky Story 2 Level 27 throws a curveball: you're not just picking clothes, you're defusing a silent rivalry. Anna's watching, and her jealousy messes with the sequence. I missed the choker my first run and had to restart. The key is to dress Riley first with edgy pieces, then soften Maddie — but Anna's reactions dictate the order. I kept dragging the floral dress early and got stuck — until I realized the game wants you to build contrast. Riley needs to steal the spotlight before Maddie can shine. Pay attention to the dialogue; Anna's "I can't let that girl steal the spotlight" tells you everything.
Pattern Overview
Tricky Story 2 Level 27 is about dressing two girls while managing Anna's envy — a fashion showdown with emotional stakes.
The Emotional Sequence
- Camisole Before Leather Jacket: Riley needs a neutral base before the edgy jacket defines her rebellion.
- Cardigan Before Tote Bag: Maddie's soft cover grounds her look before accessories add personality.
- Choker Before Sunglasses: The choker sparks Anna's jealousy, which sunglasses then amplify with mystery.
- Heavy Makeup Before Light: Riley's bold face forces the contrast that makes Maddie's natural glow more charming.
- Leather Shoes Before Headphones: Shoes set Riley's stance; headphones isolate her attitude.
- Black Socks Before White: Color clash emphasizes the rivalry before the final dress reveals who wins.
- Floral Dress Before Pearl Necklace: The dress is the centerpiece; pearls elevate it for the party spotlight.
Why This Level Feels Tricky + The Key Insight
- The order of items isn't obvious because Anna's interjections mislead you into thinking you should dress Maddie first. You see her dialogue about "Riley looks so beautiful!" only after certain steps, so you might assume any order works — but the game punishes early floral dresses.
- Some accessories like the hair tie appear late and feel optional, yet they're required to complete Riley's look and trigger the final scene. Missing them locks you in a loop. I thought I could dress both girls in any order, alternating items to keep things balanced. I put the floral dress on Maddie early, then tried to add Riley's leather jacket. Anna's line "Riley looks so beautiful!" only appeared after I gave Riley the jacket — not before. That's when I realized in Tricky Story 2 Level 27 the sequence must first make Riley the center of attention to satisfy Anna's jealousy, then dress Maddie to balance it.
Step 1. Drag the Camisole for Riley
Start with the camisole — it's the foundation of Riley's look. Tricky Story 2 Level 27 forces you to begin with a neutral base before adding attitude. Anna mutters "I knew it" as you drag it over. This step grounds Riley's silhouette, preparing for the edgy layers to come.
Step 2. Drag the Cardigan for Maddie
Now Maddie needs a soft cover. Tricky Story 2 Level 27 pairs the cardigan as her gentle start. Anna's "Thanks a lot!" echoes — she's relieved you're not ignoring Maddie. This contrast sets up the rivalry: Riley edgy, Maddie sweet. Don't skip this; the cardigan anchors her whole outfit.
Step 3. Drag the Leather Jacket for Riley
Here's where Riley's rebellion emerges. In Tricky Story 2 Level 27, the leather jacket transforms her from plain to punk. Anna's thought "Can't you stand me being the center of attention?" fits perfectly — Riley is about to steal the spotlight. The screen brightens as her outfit gains attitude.
Step 4. Drag the Denim Skirt for Riley
The denim skirt follows the jacket — can't have a top without a bottom. Tricky Story 2 Level 27 demands this sequence: jacket first, then skirt. Anna whispers "Riley looks so beautiful!" The look is cohesive now, setting the stage for accessories.
Step 5. Drag the Choker for Riley
A choker adds that punk edge. Tricky Story 2 Level 27 uses it to complete Riley's neckline. Anna's "No way... Why are all eyes on her" shows her jealousy flaring. This small item triggers a shift in the narrative — the rivalry intensifies.
Step 6. Drag the Tote Bag for Maddie
Maddie needs a practical bag. Tricky Story 2 Level 27 wants a tote to match her sweet style. Anna says "Wow, a whole treasure!" as you add it. The tote grounds Maddie's look, giving her a functional anchor before the cute charm.
Step 7. Drag the Bag Charm for Maddie
The bag charm adds personality. Tricky Story 2 Level 27 makes this a small but crucial detail — it softens Maddie's appearance. Anna's "Calm down a bit, Claire!" seems directed at the charm's cuteness. Now Maddie's bag is complete.
Step 8. Drag the Flats for Maddie
Flats keep Maddie comfortable. Tricky Story 2 Level 27 chooses them over heels to maintain her gentle vibe. Anna's "These balloons won't get wet" is oddly fitting — maybe a metaphor? The flats finish her lower half, contrasting Riley's leather shoes later.
Step 9. Drag the Leather Shoes for Riley
Riley gets leather shoes to match her jacket. In Tricky Story 2 Level 27, this step solidifies her rebellious look. Anna's "Your feathers will grow back soon" is cryptic, but the scene shifts — Riley's outfit is almost done. The shoes make her stance confident.
Step 10. Drag the Sunglasses for Riley
Sunglasses add mystery. Tricky Story 2 Level 27 uses them to give Riley an air of confidence. Anna's "You can't touch me!" fits perfectly as you drag them on. Now Riley's face is hidden but powerful. The screen reveals a new dialogue: "She looks so beautiful!"
Step 11. Drag the Heavy Makeup for Riley
Heavy makeup completes Riley's bold persona. Tricky Story 2 Level 27 demands this before light makeup on Maddie — contrast is key. Anna's "That damn girl!" erupts as Riley becomes the center. Her jealousy peaks. This step unlocks the next phase of dressing Maddie.
Step 12. Drag the Light Makeup for Maddie
Now Maddie gets natural makeup. Tricky Story 2 Level 27 balances the heavy look with subtlety. Anna's "It seems like she's planning something... I must be on guard" suggests she's wary of Maddie's softness. Light makeup keeps Maddie approachable, opposite of Riley.
Step 13. Drag the Hat for Maddie
A hat tops off Maddie's sweet style. Tricky Story 2 Level 27 places this after makeup to complete her face area. Anna's "Hey... look!" indicates the party guests notice the contrast. The hat adds a playful touch, softening her even more.
Step 14. Drag the Headphones for Riley
Headphones give Riley an aloof edge. Tricky Story 2 Level 27 uses them as a final accessory to isolate her from the crowd. Anna's "Get out of my way!" shows her frustration with Riley's dominance. Now Riley's look is fully detached and cool.
Step 15. Drag the Black Socks for Riley
Black socks match Riley's dark theme. Tricky Story 2 Level 27 forces you to choose her socks before Maddie's white ones. Anna mutters "Your feathers will grow back soon" again — perhaps meaning Riley's plumage? The black socks complete her monochrome palette.
Step 16. Drag the White Socks for Maddie
White socks contrast Riley's black. In Tricky Story 2 Level 27, this step reinforces the good-girl image. Anna's "But they look a bit different" echoes the visible difference. The socks are a small but clear visual cue of their opposing styles.
Step 17. Drag the Belt for Riley
A belt cinches Riley's waist. Tricky Story 2 Level 27 places it here to structure her outfit before the final dress. Anna's "I can't let that girl steal the spotlight" confirms your progress. The belt adds definition, making Riley's silhouette sharp.
Step 18. Drag the Leather Bag for Riley
Riley gets a leather bag to match her shoes. Tricky Story 2 Level 27 saves this for near the end. Anna's "You lost again" is aimed at Maddie? The bag completes Riley's accessory set. Now her look is fully coordinated and intimidating.
Step 19. Drag the Floral Dress for Maddie
The floral dress is Maddie's centerpiece. Tricky Story 2 Level 27 holds it until after Riley's accessories are done. Anna's "You look very beautiful today. Wanna hang out over there?" is said to Maddie — a boy notices her. The dress transforms her from plain to party-ready.
Step 20. Drag the Pearl Necklace for Maddie
Pearls elevate the floral dress. Tricky Story 2 Level 27 adds this as the final touch for Maddie. Anna's "Alright!" signals acceptance. The necklace adds elegance, contrasting Riley's choker. Now both girls are complete — the rivalry is set.
Step 21. Drag the Hair Tie for Riley
The hair tie is the last item. Tricky Story 2 Level 27 uses it to give Riley a practical finish. Anna's "Just let me borrow it for a bit" might be about the tie? This step locks Riley's look. Now the scene transitions to the party with both outfits perfect.
The Logic Behind It
The method for Tricky Story 2 Level 27 is to build Riley's edgy look first to trigger Anna's jealousy, then dress Maddie softly to balance the spotlight. Each item either escalates or soothes the rivalry based on the emotional contrast required.
Final Scene Description
When I finished the last drag, I watched Riley and Maddie walk into the party. Riley's leather jacket caught the light, her sunglasses hiding her eyes. Maddie's floral dress swayed as she smiled. Anna stood in the corner, muttering "That damn girl!" under her breath. The pearls on Maddie's neck glowed. Tricky Story 2 Level 27 ended with the perfect contrast between punk and sweet.