Adam Glassman
Photo: Alex Beauchesne
1. You can never go wrong in a little black or red dress.

2. I love dressed-up denim. Dark wash jeans paired with a shiny or embellished top makes a great look for an afternoon event.

3. Let's say you wear all black or neutrals—you can instantly update your look with a long, oblong scarf (as opposed to a square, silk scarf) in a chic pattern. Find bright styles at Club Monaco and pretty, ruffled versions at the Gap.

4. Mix fancy pieces with everyday items. Do a dressy top with jeans or a gray flannel pant with a silky top. Instant party outfit!

5. My rule is: Shop your own closet. Pair together things you never would for a completely different look.

6. If you're going to buy something, buy one special thing that will get you through more than just the holidays. It should last you into early spring. No guilt if it's a piece you'll wear forever.

7. An on-trend handbag or a shoe automatically updates your look. For extra oomph, try a satin shoe in a bright color.

8. Consider a clutch. Yes, this trend will be around for a long time.

9. Anything metallic goes. Clothing, shoes, bags, accessories—you name it. They're classic and seasonless—and all over the spring 2009 runways.

10. Wear cashmere! Get a sweater or a top in a fun color. Uniqlo is great—and cheap! Turtlenecks are $89.50; cashmere blended V-neck sweaters are $49.50.

11. Don't rule out pants: The tuxedo suit is a great holiday outfit. Wear it as a suit, or the pant or jacket alone. Express and Bebe have both for reasonable prices, or check your local vintage store.

How to Accessorize

12. The number one accessory is a statement necklace. For a vintage feeling, wear one with a lot of rhinestones.

13. Number two: big bangles. No need to splurge either—Claire's Accessories is great for these types of things. Banana Republic and J.Crew also have great jewelry.

14. Number three? A big, giant cocktail ring. They're everywhere! Loulou de la Falaise has an inexpensive, great line on HSN.com.

15. Go big and bold with hair accessories. Feathered clips are in! It's an instant way to be festive without spending a lot of money.

16. If you do go with a statement hairpiece, keep the jewelry to a minimum. You don't want them to compete.

17. Keep nails dark or metallic.

What to Avoid

18. Three words: Big. Holiday. Sweaters.

19. A matching set of jewelry. If you go with the statement necklace, skip the earrings (or wear a small, simple pair); if you wear large earrings, skip the bold necklace.

The Bottom Line

20. You should never look like you tried too hard. You want to present a notched up version of yourself—not a completely different person.