The Looks

Après, Not Ski

Cropped fur, tall suede boots and Chanel shades for the glare. Nobody needs to know you never clipped in.

• Bomber JacketsVintage Y2K Purple Bolero Cropped Rabbit & Fox Fur Jacket Coat $245 Gone
• Manolo BlahnikManolo Blahnik Brown Suede Knee High Boots with Scallop Trim $750 Shop on eBay
• SunglassesChanel Y2K Camellia Flower Shield Sunglasses $378 Gone

Wedding Guest, Capri

Silk chiffon that moves, a low heel for cobblestones and a beaded clutch small enough to forget you are holding it.

• DressesMarjone 1920s Red Silk Chiffon Polka Dot Dress $395 Shop on eBay
• Manolo BlahnikVintage Manolo Blahnik Beige Pink Houndstooth Pointed Y2K Bow Mule Kitten $325 Gone
• La RegaleLA REGALE BAGS BLACK BEADED CLUTCH PURSE $25 Shop on eBay

The look: $420 across 2 pieces. Each one links to its own listing.

Festival, Grown Up

One piece of fringe, Cavalli flares in a colour you would not wear anywhere else and a proper heeled boot. Cowgirl without the costume.

• Tank TopsHandmade Black Leather Fringe Halter Top - Beaded Feather Detail $125 Shop on eBay
• JeansJust Cavalli Blue Python Print Jeans $212.49 Shop on eBay
• BootsGianmarco Lorenzi Limited Edition Cowboy-Style High Heel Boots $680 Shop on eBay

The look: $1,017.49 across 3 pieces. Each one links to its own listing.

Honeymoon, Dinner at Nine

Ivory satin to the floor, Galliano era Dior sandals and oversized Gucci frames you will keep on longer than you should.

• DressesVintage Cache Off-White Satin Maxi Dress $110 Shop on eBay
• Christian DiorChristian Dior by John Galliano Red Leather Diva Mule Heels $1,099 Shop on eBay
• GucciGucci GG 1100 Aviator Sunglasses Frame, Brown & Gold $169.15 Shop on eBay

The look: $1,378.15 across 3 pieces. Each one links to its own listing.

The Office, Upgraded

A lace corset blazer over whatever black trousers you own, a pointed kitten heel and a big canvas tote that fits a laptop.

• Dolce & GabbanaDolce & Gabbana 1990s Corset-Style Lace Blazer $259 Shop on eBay
• HeelsPrada Vintage Mustard Yellow Slingback Heels $150 Shop on eBay
• Ralph LaurenPolo Ralph Lauren Pony Canvas Tote Bag, Black $65 Gone

The look: $409 across 2 pieces. Each one links to its own listing.

Print on Print

Printed denim, snakeskin heels and a Zucchino Baguette to pull it together. Y2K did not believe in restraint.

• PantsRare Vintage Roberto Cavalli Crocodile Print Sand Pants $200 Gone
• HeelsManolo Blahnik Snakeskin Leopard Print Pointed Toe Slingback Heels US 6 $259 Gone
• FendiFendi Mamma Baguette Bag in Pink Zucca PVC $980 Gone

The Tom Ford Hour

A bias-cut slip, GG mules and a horsebit clutch. The 90s Gucci formula still works because nothing competes with it.

• Dresses90s Y2K Light Cornflower Blue Glass Beaded Bias Cut Slip Dress Size Medium $85.75 Shop on eBay
• GucciGucci GG Monogram Square Toe Kitten Heel Mules $650 Shop on eBay
• GucciVintage Gucci Horsebit 1955 Clutch - Tom Ford Era - Brown Caramel Monogram $2,000 Shop on eBay

The look: $2,735.75 across 3 pieces. Each one links to its own listing.