Holiday Attire Do’s & Don’ts

Written and styled by Tracy James
Photography by Chuck St. John

December delivers smiling family photo-emblazoned greeting cards, as well as invitations to gatherings with stressful dress code instructions like “festive attire” and “holiday cocktail.” First of all, let’s talk about what NOT to wear to these seasonal fetes. While I am a wardrobe stylist who rarely quotes hard and fast rules, this is a worthy exception. Do not, do not, DO NOT wear any garment that features reindeer, wreaths, snowmen, holly berries, etc. In fact, resist the temptation to wear red and green together, period. You will just end up looking costume-y, cliché, and like you are headed to assist the local mall Santa. The fact that there are tacky Christmas sweater parties being held across college campuses should be a huge red flag. Also, resist seasonal accessories that include but are not limited to ceramic or plastic (gasp!) snowman pins, bell earrings, themed scarves, and flashing Christmas tree broaches. Rudolph’s red nose blinking in the 1964 stop-motion animation classic is one thing—on your lapel is quite another. With the exception of a watch, jewelry should not have batteries.

Now, I can appreciate the desire to be a little festive during the holidays; I welcome the opportunity to kick up the flash a notch. But there is a way to be high-spirited without being hokey. Metallics and sequined garments have evolved from trendy to firmly classic, and both accents are a great way to add a little sparkle to an ensemble. Think black sequin pants paired with a cold-shoulder metallic knit sweater. Fur embellishment (either real or faux) can add a celebratory element, as can bold color. Look for rich jewel tones, such as emerald, plum, and peacock blue, as well as vibrant shades, such as tomato red, cobalt blue, and fuchsia. Incorporating black is a great way to ground bolder tones as well as keep the look decidedly nighttime.

Accessories are an important part of holiday dressing. Select beautiful, interesting jewelry that will last you throughout the year and coordinate with a variety of outfits, not just holiday attire. Even then, don’t get carried away. Choose focal pieces, instead of over-accessorizing, but don’t be afraid to try statement pieces. Anything too delicate will simply get lost on you. Try chandelier earrings, chunky cuffs, multi-layer necklaces, and sparkly cocktail rings—just not all at the same time. The statement that a piece of jewelry is trying to make gets lost if there’s too much going on all at once. A good rule of thumb is to give some breathing space between bold pieces, so instead of big earrings AND a big necklace, try big earrings and a cocktail ring or embellished cuff.

Above all, be joyful! ’Tis the season to spread cheer, so start with your appearance. When you feel good about what you have on, it shows and inspires others.


1. A Sassy, Short Cocktail Dress – either in a metallic, a dressy material like double ply silk satin or jacquard, and/or with a little sparkle or embellishment
2. A Chic Evening Clutch – sized only to hold the essentials like lipstick, an iPhone, and a credit card
3. An Evening Coat, Jacket, or Wrap Nothing ruins a party dress more than throwing on a big bulky overcoat over it. Even worse is wearing your husband’s suit jacket by the end of the night! An appropriate outer-layer can be anything from a knee-length satin coat to a cashmere wrap to a tailored leather jacket. To ensure the most wearability, choose black or a metallic.
4. Bold Jewelry – like a statement necklace, jeweled cuff, or cocktail ring
5. A Statement Shoe – With gorgeous options in stores this season, shoes are a great opportunity to add color, texture, or bling to an ensemble.

For the classic ladies: The exaggerated shoulder-to-back bow detail on this Tahari ASL floral jacquard shift dress (Belk, $138) makes it dramatic and demure at the same time. The addition of pockets makes it even better. To match the boldness of color and texture, a perfect addition is statement accessories in the form of a stretch rhinestone cuff (Etsy, $35) and limited-edition Nina “Isabell” crystal-covered black suede pumps (Belk, $129).


For those who want long sleeves: This Nanette by Nanette Lepore ruffle-neck shift dress is a great go-to. To amplify it’s cocktail appeal, add a dramatic chandelier earring (vintage, stylist’s own) and a statement shoe  – here, the festive Nina “Reign” merlot velvet peep-toe pump (Belk, $99). This look could be taken in a slightly more casual and edgy direction by paring it with opaque hose (my favorite are Hue’s Super Opaque) and black suede high-heeled booties.

For those who prefer pants: A slim, tailored ankle pant in a dressy fabric is not only tres chic, but versatile as well. Pair with a structured jacket, Jackie O inspired knit, or evening blouse. Trina Turk “Aubree” pant (Saks Fifth Avenue, $268); Calvin Klein flutter-sleeve top (Belk, $79.50);  Pour La Victoire “Camilla” Pom-Pom pump (Belk, $325); Betsy Johnson “Garden of Excess” necklaces: mesh bow and lightweight gold (Belk, $52 and $75).

For the bohemian: Someone who prefers flowy over structured might like this Michael by Michael Kors Leopard Print Cold-Shoulder dress (Michael Kors, $225). Jessica Simpson “Bliths” Booties (Belk, $119) keep the look modern, while an Ann Taylor jeweler leopard broach (Ann Taylor, $39.50) pinned to a Nina “Keiko” clutch (Belk, $55) adds sparkle.

For the Tomboy: Staying true to your own personal style year-round is important. Just because you’re not a dressy girl doesn’t mean you can’t don appropriate party attire. Familiar textiles like leather and 90’s vibe plaid combine with minimal accessories for an overall look that is holiday-ready.  Jessica Simpson “Rosalind” dress (Belk, $119) French Connection “Chariot” jacket (Belk, $218), Stella & Dot “Marcel” Collar necklace (, $39); Nadri oversized gold hoop earring (Belk, $65); Nina “Alexy” clutch (Belk, $45)

For those who demand comfort: Festive doesn’t have to mean structured, certainly should never be stuffy. If you have a relaxed style, try this Vince Camuto metallic cold-shoulder sweater with Free People’s “Just a Dreamer” sequin pant (Free People, $148). Betsy Johnson “Skeletons After Dark” long necklace (Belk, $75) + vintage strands (stylist’s own); Jessica McClintock lurex miniaudiere (Belk, $36); Jessica Simpson “Bliths” bootie (Belk, $119)

Other Favorites

Limited-edition Nina “Isabell” crystal-covered black suede pumps (Belk, $129)

Nina “Reign” merlot velvet peep-toe pumps (Belk, $99)

Betsy Johnson “Garden of Excess” necklaces: mesh bow and lightweight gold (Belk, $52 and $75)


Nina “Keiko” clutch (Belk, $55) and Ann Taylor leopard broach (Ann Taylor, $39.50)



Leave a Reply