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How To Show Up With Style & Confidence For The Holidays

Debra Schwartz Images November 2022 2

Signature Styling Thought Leader: Debra Schwartz

November ushers in the holiday season.

“Are you ready to get dressed and show off your style?”

Every year it’s the same thing—once the Halloween decorations come down, the social season amps up. Before we know it it’s Thanksgiving, Black Friday, and then the heart of the social season. Are you ready to get dressed and show off your style? Styles for the holidays is a whole new ball of wax.

You can prevent that staring into a closet-full-of-nothing-to-wear feeling, the one that makes you feel like “just phoning it in” for that night’s invitation. Take the time now to get holiday-ready and eliminate that inevitability. You want to totally step into the party feeling festive and fabulous!

Use This Three-Step Style Strategy And Enjoy Stress-Free Dressing:


Assess what you already have in your wardrobe, strategize what things you need or want, and create your outfit options in advance:

Take time now to do a little early intervention, a wardrobe prep, and save the stress of getting dressed at the last minute for those planned or popup parties. This is a surefire way to prevent hurried compromise outfits that fall short of making you feel fantastic.

This means assessing your wardrobe now, to take inventory of your “holiday-wear”. Figure out what you’ll need or want so you can be on the lookout (before sizes are scarce). I know this feeling, especially when it came to shoes. The boots that I hesitated to buy early in the season (hoping for a markdown) were going gone by the time I was ready to pull the trigger.

This goes for online shopping as well as in-store. The stores carry far less than ever before. When you shop online, add time for delivery and possible exchanges.

TIP: Look at reviews for comments on sizing and quality for brands you don’t typically wear. You may be able to pick up the fill-ins and finishing-touch pieces that “make” the outfit during the post-thanksgiving shopapaloozas. When you plan, you’ll prevent last-minute compromise buys. They’ll always seem like also-rans, not things that give you style-confidence. 

Find New Ways To Style:


Look at the sites, blogs, PINTEREST pages, and magazines to spark ideas.

“Take cues from what you see and make a note of what grabs your attention.”

Stop relying on the “same-old, same-old” go-to outfits from holidays past by simply sleuthing a bit. Resources are at your fingertips, literally. Is there an influencer whose style you love? Or a designer or brand that features how-to holiday looks on their site? Take cues from what you see and make a note of what grabs your attention. Use these finds for styles for holidays outfit ideas.

Find new ways to style things you already own by searching on PINTEREST —type in the item (for example: outfits with black velvet blazer) within search bar. Results will be images of outfits that you might be able to replicate with what you own or provide you with ideas on what you may want to buy.

TIP: Use GOOGLE LENS to find similar items: simply take a screenshot of an item or upload a personal photo of an item you want to locate. GOOGLE LENS will come back with shoppable items from stores as well as Poshmark and Ebay.

Styles For The Holidays – Classic Jewel Tone Colors:


From classic looks to on-trend outfits style, your choice of shoes, bags, and accessories can easily update and upgrade.

So, what are we going to wearing? First thing we all think of for styles for the holidays are classic pieces that are a bit more sparkly, with more luxe textures in classic jewel tone colors like red, dark green, blue and, of course, lots of black. Satins, velvet, sequins, and lurex lead the looks for a dressier event like a cocktail party or a black-tie event – all things synonymous with the season. 

“Shine has come out of the night and into the day.”

However, the trend is towards mixing high and low both in type of clothing and in materials, which allows our wardrobe to work for us double-duty. That’s smart dressing (and shopping!). Shine has come out of the night and into the day. So, top the satin skirt is with a bulky pullover, or throw a tweedy blazer, belted, over a satin slip dress, and wear boots with both looks.

Always Keep The Proportions:

The beauty of these looks are that they can smoothly transition from day to evening with a quick change of shoes and accessories. Replace daytime boots with edgy platform sandals, your structured crossbody with a soft clutch. Great news: the rules do not apply anymore! For example, I love pairing sequin skirt with a crisp white tailored button-down and strappy sandal.

And the coated denim jeans are a fantastic foundation for anything from at-home parties to club nights (again, it’s the shoes and bag that shift the mood and attitude). 

TIP: Always keep the proportions balanced to ensure the most flattering look: for instance, a slimmer skirt calls for roomier top and vice versa. A wide-leg trousers look especially leg-lengthening with a more fitted waist-cropped top.

Keep A Record:

NOW document your holiday looks with a photo. Keep it in its own album on your phone and/or create a PINTEREST board of these looks and have a ready reference.

Download my HOLIDAY WARDROBE list of essentials and trends, and CHEERS to a fabulous you for the holidays, and for every day!

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About the Author:

Debra Schwartz, of CRUSH.STYLE, is a stylist and designer with more than three decades in fashion, cosmetics, corporate design, branding, and digital media.

As a Confidence-Creator, an Amplifier of Self-Image, and an Architect of Empowerment for women her goal is to have you show up with confidence and style in chapters two, three, (or four!) of life. “My passion and mission is to bring elevation and joy to women through signature style… and reclaim your fabulousness”.  

Find Debra on Instagram @crushstylenow. Visit http://www.crush.style to learn more about Debra and how her signature style services can elevate you to the next level.