Great — here are the best places in Singapore to shop for authentic Y2K pieces (especially dresses-over-trousers looks), plus quick tips on what to hunt and where to check online.

Brick-and-mortar neighbourhoods and stores

• Haji Lane / Kampong Glam — the epicentre for curated vintage and Y2K-friendly boutiques: Vintagewknd, Flame Vintage, Two Worlds and other independent shops there carry frilly camis, slip dresses, reworked pieces and one-off Y2K finds. These stores are great for dresses you can layer over trousers. (girlstyle.com)
• Golden Landmark / Bugis area — multistore thrift hubs and $10 thrift outlets (e.g., Woofie’s Warehouse, Lucky Thrifty) with lots of streetwear, baggy pants and retro tops you can pair under dresses. Good for budget Y2K staples like cargoes and graphic tees. (confirmgood.com)
• Queensway Shopping Centre — known for secondhand and rework stalls (Bhabie’s Market, Un Wastelands) with Y2K silhouettes: low-rise/flare trousers, mini skirts and oversized outerwear. Useful if you want authentic early-2000s bottoms to layer under dresses. (fzine.com)
• Bras Basah / Orchard / Lucky Plaza bazaar — several multi-vendor thrift/consignment spaces that refresh stock often; good for digging out unique dresses, sheer tops and small accessories (but requires rummaging). (blog.maxthon.com)

Online / social resale (fastest way to find specific Y2K pieces)

• Instagram-based thrift shops and regular drops (examples: @retrothriftsg, @seasonthrift.sg and many curated sellers) — follow for scheduled restocks, themed drops and DMs to buy. These sellers specialize in 90s–Y2K items. (shopperboard.com)
• Carousell (local classifieds) — huge local resale market where many sellers list Juicy-style velour, slip dresses, low-rise jeans and late-90s/00s branded items. Search with “Y2K”, “2000s”, “slip dress”, “low rise” or brand names. (mothership.sg)
• Regional marketplaces (Shopee, Lazada) — cheaper fast-fashion Y2K-style pieces and accessories if you’re after trend versions (not vintage/authentic). Good for experimenting before committing to a one-off vintage buy. (mothership.sg)

Specific store tips for “dress over trousers” styling

• Look for long slip or maxi dresses, mesh or sheer dresses, or short sundresses in Haji Lane / boutique stores — layer over straight-leg low-rise trousers, capris or flared jeans (Queensway and Bugis are good for those bottoms). (girlstyle.com)
• Hunt for lightweight sheer blouses, long camis and corset tops in curated thrift stores for layering under/over dresses. Two Worlds and curated Haji Lane shops frequently stock these. (femalemag.com.sg)

Extras — markets & events

• Pop-up markets and vintage weekends (check Vintagewknd pop-ups and local market listings) — good for unique one-offs and reworked pieces. (girlstyle.com)

Quick practical advice

• Follow shops on Instagram/TikTok — most small vintage stores and IG sellers restock and announce drops via social. (shopperboard.com)
• If you want authentic labels (Juicy, early 2000s denim), prioritise Queensway and Haji Lane hunts. For budget/fast-fashion Y2K looks, check Shopee/Lazada listings. (fzine.com)

If you’d like, I can:

• Pull together a 1-day shopping route (Haji Lane → Bugis/Golden Landmark → Queensway) with addresses and opening hours, or
• Search current Instagram sellers and list active accounts that have recent Y2K drops.

Which do you prefer?