Holiday Party Dressing – The List

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by Allison Hamilton-Rohe

In the run-up to the holidays, nothing provokes outfit panic like the holiday party.  This year, I’d like to suggest a different approach to the holiday party — think of it as just as important as the presentation you lobbied to give, the coffee you’ve set up with a new lead or the talk you volunteered to do at your upcoming conference.  Holiday parties are an opportunity for visibility.

Putting Together the Look

When putting together a new look, there are a couple angles I consider when interpreting my own or a client’s personal style:  the trends, color story and style language.  For the holiday-party look, Style Language rules all!

  • Leveraging the Trends:  Trends this season lend themselves beautifully to holiday dressing:  sparkle, velvet, jumpsuits and printed suits are all great go-to items for this event.  To read more on this season’s trends, click here.
  • Color Story:  This season, your holiday look is less about color story and more about texture and fabrication due to the trends.  To read more about color story, click here.
  • Style Language:  Because you’re focused on making a positive impression and the trends this season are all about texture and fabrication, style language is everything.  It’s about looking composed and polished, elegant and sophisticated and rounding out your peers’ image of you while burnishing your visibility with those senior to you.  This is achieved through sharp tailoring, modest necklines and sleeve length and those luxurious fabrics and textures.

The Shopping List

The Dress:  Eliza J Velvet Wrap-Inspired Dress ($118)

velvet dress, holiday party, personal style, the three tomatoes, how-to, working woman wardrobe

This universally-flattering style in a universally-flattering color is an instant classic for your holiday party.  Dress it up with a statement necklace or keep things simple with stud earrings.  Pair it with suede boots or heeled loafers to make it more practical for Winter.  Finish your looks with a simple clutch to hold your wallet, keys and phone.

Available in 0-18.  For a Plus size option, try this fit & flare Millie Dress ($108).  For another Petite or Misses option, try this Alex Evenings Dress (ON SALE $113).

The Jumpsuit:  Eliza J Surplice Jumpsuit Misses ($148) or Plus ($168)

jumpsuit, holiday dressing, how-to, working woman, the three tomatoes, personal style

This fabulous jumpsuit will stay fabulous all year ’round.  Dress it up with a statement necklace or keep things simple with stud earrings.  Pair it with suede boots or heeled loafers to make it more practical for Winter.  Finish your looks with a simple clutch to hold your wallet, keys and phone.

Available in 0-18 or 14W-24W.  For a different take, try her Bell-Sleeve version in Misses or Petite sizing ($138).

The Blazer:  Halogen Satin Blazer Misses or Petite or Plus ($99)

satin, blazer, wear to work, holiday party, holiday dressing, working woman, the three tomatoes,, personal style, how-to

Pair this fabulous satin jacket with velvet jeans or leather leggings for a more casual holiday-party look or layer it over the velvet dress or jumpsuit for extra coverage and polish.

Available 1X – 3X, XSP-XLP and XS-XL.

The Necklace:  BaubleBar Crystal Statement Necklace($68)

statement necklace, holiday dressing, holiday party, the three tomatoes, how-to, personal style, working woman

This fabulous portrait necklace reminds me of RBG’s or Elizabeth I’s amazing lace collars.  Use it to evoke a most feminine type of power.  The color palette is white and clear, to indicate (ahem) clarity and a fresh start for every new project.

The Earring:  Kate Spade Pave Earring ($44)

fashion, holiday style, stud earrings, the three tomatoes

Simple, elegant and understated, these earrings allow your face to take the stage while adding the requisite sparkle and shine to the occasion.  Depending on your skin tone, go for gold (warm) or silver (cool) to reflect the right kind of light onto your face.

The Loafer:  Sole Society Heeled Loafer ($85)

Thanks to Michelle Obama, we can now wear flats with dresses and jumpsuits, but some women do need a little heel.  Whether it’s for your heel spur or just to elongate the leg, this heeled loafer is comfortable, provides a little lift and remains practical for winter wear.

Available in 5-11.

The Boot:  Geox Felicity Knee-High Boot ($274)

knee-high boot, suede boot, problem feet, working woman, holiday dressing, what to wear with dresses, working womanWondering how to pair a dress and Winter weather, problem feet or both?  Problem solved!  I wear my suede knee-high boots almost exclusively from November to March with absolutely everything from jeans to dresses for every occasion.  The suede lends elegance, the height of the boot elongates your overall look (plus it’s warm) and the flat nature of the boot keeps you grounded in any kind of weather.

Available in 5-10.5 or 35-41 EU.  For removable arch-support and sizing to 11, try Born’s version ($219) or a wide-calf option, try Vince Camuto’s version (ON SALE $150) or at a lower price point, try Chinese Laundry’s version ($99).

The Clutch:  Nina Avis Pleated Classic Clutch ($45)

holiday style, style tips, clutch bag, the three tomatoes, style how tosThis classy, inexpensive clutch finishes your look for evening.  Stow your phone, keys and wallet in this beauty, use the strap when navigating drinks and hors d’oeuvres or “clutch” it under your arm as the name implies.  Many women neglect this key accessory for evening but it is final element for you to look complete head-to-toe.

The Lipstick:  Sisley Hydrating Long-Lasting Lipstick($57)

classic red, sisley, long-lasting, lipstick, personal style, thethreetomatoes, working woman, holiday partyThere is nothing more classically feminine yet progressive than a bold, red lip — just ask Aryanna Priestly or Alexandra Ocasio-Cortez, our two breakout female political stars this season.  Even if you normally do not wear make-up, the bold, red lip is one you might want to consider employing for your holiday look.  This formula is beautifully long-lasting, the packaging is beautiful and Sisley is well-known as an early pioneer in the use of plant extracts and essential oils for wonderfully-effective skin care and make-up.

Styling The Look

From head-to-toe, we want to be sure your look is fully composed.  Wash and style your hair down or up, do your make-up or spritz on fragrance if you wear it.

The Dress Look:

The Jumpsuit Look:

The Satin Jacket Look:


Allison Hamilton-Rohe is a Personal Style Coach. Through her unique formula, she helps you create a personal style you can inhabit with ease.  She is a global nomad who currently lives in Silver Spring, MD with her husband, two kids and a sweet Dutch bunny.  Would you like to learn more about how to create your personal style and inhabit it with ease? Sign up today to receive your Personal Style Starter Series

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