Leslie Willmott | Wardrobe Strategies for Career, Travel & Casual Lifestyles

Wardrobe Strategies for Career, Travel & Casual Lifestyles

Easy Wardrobe Strategies for the Holidays

By on Dec 1, 2017


shutterstock_526014424The holiday season has arrived and with it the fun and frenzy of parties and pageants, cocktails and dinners. What to wear to meet the multiple demands of the season?

If you streamline your wardrobe you won’t waste time and energy wondering. Don’t get stressed – keep it simple and follow these guidelines:

•  Make a list of what’s on your calendar, special events you’ll be attending, and when you’ll need to go from one venue to another (for example, from the office to a cocktail party; from a day of sightseeing right into dinner; or from your child’s school event to a holiday concert).

•  The good news is that “dressing up” is no longer the norm. But you do want to look polished and put together. Choose just a few go-to pieces that will meet your needs. These looks can be as subtle or overt as you like, but the goal is that these pieces be versatile, comfortable, and stylish and make you feel great!

•  If a party invitation specifies attire such as “cocktail” or “semi-formal”, or “festive” or “casual chic” read my previous holiday post for guidelines on how to interpret holiday dress codes.


Streamline Your Dressing

Office to Party

Start with one core item and build from there. Here are three strategies for three lifestyles:

1. Career – Your core might be a dress or a suit. Use accessories and fabrics to change your outfit from desk to dinner-appropriate: Switch to a silk or silky blouse and from your classic pumps to a strappy heel for the evening.

Note: If you have a holiday business event to attend, you’ll want to wear something business appropriate that also feels festive. No slinky or overly sexy dresses! Let your jewelry, or perhaps a satin blouse, add the holiday flare to your business suit, be it with a skirt or pant.

2. Casual – Think “casual chic”. Start with a pant, legging or dark wash skinny jean. Then choose a top for each event on your list. You might find a glittery sweater on sale! And you can get lots of mileage from one pair of dark solid-color pants – no one is going to remember you wore them at the previous party.

•  If leggings are your bottom choice, be sure your top is long enough to cover your backside! If choosing a jean or pant you can opt for a shorter, more fitted top.

Casual Holiday•  Pair a weekend staple with something glamorous — for example, a nice pair of dark jeans with a bow blouse or glittery top. 

•  Slip on a pair of embellished flats or heels, perhaps something in a glittery metallic.

3. Travel – Scarves, costume jewelry and glitter – in a top, a shawl or scarf – and an evening clutch are my favorites for dressing up basic black pants and a long-sleeved black tee that can take me from museum to shopping to dinner on a holiday city visit. I’ve also packed red flats, a red belt and sparkly earrings for festive Christmas evening accents on my basic black pieces. For New Year’s Eve, I switch to gold!

A note about “sparkle”: Don’t overdo it; moderation is key but you want it to have an impact. Stick to one or two pieces of jewelry and don’t forget a dressier bag or clutch – anything that has a little bit of sparkle. Accessories should relate but they don’t have to match.

With so much else going on, now is the time to stick to what you know, and most of all, what feels good. Just because it’s comfy doesn’t mean it’s not chic – when you choose the right pieces, your simple uniform can take you through your day and into your night without missing a beat! That’s being smart!


Do you have the pieces but lack the confidence to put it all together for this season’s parties? Or do you need a little guidance on exactly what to buy to fill your party wardrobe gaps? Don’t hesitate to give me a call or send me an email for a complimentary 30-minute consultation. It will be my pleasure to assist you!


  1. Leslie,

    Thanks. So very timely. A great help for my holiday events.

    Merry Christmas and Happy New Year to you and Jeffery,


    Carole DeDomenico

    December 1, 2017

  2. Thanks Leslie for such practical tips. I was almost ready and now i have a plan!! Have a great Christmas! Ann

    Ann Ashley

    December 1, 2017

  3. Wonderful advice and so timely!

    Susanne Nehlsen

    December 1, 2017

  4. What to pack to wear outdoors shoes wise in NY at New Year


    December 2, 2017

    • Hi Monica, as the weather will be cold my advice is to wear warm, flat boots for walking. And be sure to spray them with a water repellent shoe spray before you leave. If you have an evening event to attend think about packing a bootie, unless it’s a more formal event, then be sure you can take a cab or Uber! And depending on where you’re going you might be able to wear your boots there and carry your evening shoes, checking the boots and changing before you enter the main event. Have a great time! By the way, you might want to read about my December 2016 trip to NYC — and what I packed — in our Tips for Travelers newsletter. Click here.

      Leslie Willmott

      December 8, 2017

  5. Thanks Leslie!
    Classic and easy! This is a great plan. Thank you for sharing!


    December 3, 2017

  6. Thank you all for your nice comments and holiday wishes! Here’s to stress-free planning and dressing for all of the events on your calendar!

    Leslie Willmott

    December 8, 2017

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