September 25, 2006 12:00 PM

“I rarely wear the same bag two days in a row,” says Nicky Hilton. “And I never throw one away.” Do the math, and it’s not hard to see how this clothing and bag designer might end up with the 300 purses that she estimates now clog her closets. “I always try to match my shoes and belt with my bag. It ties a look together,” says Hilton, who this November will add hotelier to her résumé with the debut of a Nicky O hotel in Miami and later one in Chicago. Here’s the inside scoop on what she takes out on the town.

Nicky by Day

“I tend to like big bags because I have a lot of stuff to carry,” says Hilton, who counts this two-tone Balenciaga among her favorites. “It’s floppy and cute.” And that stuff inside? Much of it is of her own design.

CONTENTS

1 Judith Leiber card case

2 Giorgio Armani lip gloss

3 Car keys on a “7” key chain from the Samantha Thavasa by Nicky Hilton collection

4 Samantha Thavasa by Nicky Hilton wallet

5 Laura Mercier makeup brush

6 Sidekick

7 Scott Barnes bronzer

8 M.A.C Studio Fix

9 Apple iPod

10 Chick by Nicky Hilton scarf

11 Chick by Nicky Hilton ring

12 Disposable camera

13 Valentino aviator sunglasses

14 Chick by Nicky Hilton “Icing” lipstick holder

15 Chick by Nicky Hilton notebook

16 Rosebud Salve lip gloss

17 Chick by Nicky Hilton cell-phone holder

Nicky by Night

While not a fan of the clutch (“You lose them,” she says), Hilton saw Sarah Jessica Parker carrying this Judith Leiber bag and fell so hard she got two: one in silver with black initials and one the other way around. (The O, by the way, is for Olivia, Hilton’s middle name.)

CONTENTS

1 Car keys

2 Cell phone

3 Judith Leiber card case

4 Giorgio Armani lip gloss

Watch it! Go to people.com/bestandworst and see Nicky talk about her handbags.

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