My friend Karey (the same one who told the heartwarming story about cardinals) has the best style. She has a major talent for finding eye-catching, glam, quirky, silly-chic pieces that make me smile, and make me want to up my fashion game.

She’s definitely who I would pick to dress me for a holiday party, so I thought it would be fun to ask her to share some holiday style tips and what-to-wear inspiration. And she found the best stuff!

Here’s what Karey says:

Whenever I get dressed to leave the house, I like to wonder if Jenna Lyons would approve. Probably she would not, but still I try. Style is all about the try, I think. But this approach can get me into trouble IRL because sometimes people mean it when they tell you an event is business formal or Wednesday casual, and then frown when you arrive in a tuxedo jacket and frayed denim. For both events.

I went to a ball a few weeks ago, and I just know Jenna would’ve approved of my dress. It was a long jersey tee, basically, but with a super deep vee. There was also a high slit. (It was this one except in black, and I paired it with this bag, which was too small for my phone, but ample enough for my EOS and a handful of Sweet Tarts.)

Harmless but interesting, I thought. Except. I did not take into account the amount of cleavage this tee dress of sorts showed.

It was kind of painful. And that’s all I’m prepared to say about that.

At the end of the night, after everyone tried valiantly for hours to look me in the eyes during our conversations – except for one lady drinking Fireball straight from the bottle, who passed me with a loud “Great boobs! Love ’em! Good job on the boobs!” at least three times – I spotted a woman with a similar neckline, or lack thereof.

“HEY!” I kind of yelled-sobbed. “I LOVE YOUR DRESS!”

I think she understood what I meant because she grabbed my hand tightly and leaned in like a sister.

“I KNOW.” she hisspered. “I saw you earlier and then I didn’t feel so bad!”

Wait. What?

Anyway. Except for that night, I am very good at dressing for events without breaking the bank. Here are a few holiday style tips for approaching holiday outfits with joy, and zero last-minute stress-purchases of LBDs and crushed velvet numbers you won’t wear again ’til maybe next December.

Collect conversation-sparking accessories. Make it easy for other party-goers to strike up a chat with you. Think quirky evening bags, standout chokers, and mismatched earrings.
Lipstick Tube, That’s a Wrap, Smiley Clutch, Velvet Bow Clutch, Mismatched Angel Earrings, Burst and Tassel, Leaf and Flower, Red Beaded Choker, Crystal Wrap, Ruby Red Velvet Cuff, Supernova Bib

“Faux Faux Faux! Merry Christmas!” One of my favorite responses to “Oh! Is that real?” stays in my head. “Can you see it?” I think to myself. “Then it must be real!” I love guilt-free – both for furry friends and my wallet – holiday wardrobe additions. Bonus: Other partygoers want to pet you.
Faux Fur Cuffs, Bag Charm, Cuddle Up Pouch, Swan Key Fob, Stole, Laceless PomPom Sneakers, Drusy Stone Ring, Emerald Green Stone, Regal Brooch Embellished Heel, Faux Fur Vest, Cross Body Bag

Metallic makes an entrance. Even better? It catches all the light in a room full of Little Black Dresses.
Silver Sandal, Pleated Midi, Illuminating Highlighter in Twilight, Metallic Skinny Scarf, Triangle Rhinestone Drop Earrings, Cold Shoulder Metallic Top, Copper Prom Skirt, Tom’s Gold Desert Wedge, Bronze Block Heel Boot

One last thing I tell all my friends before fancy gatherings: Don’t wear anything you have to tug on or starve in, and for goodness sake take advantage of the thick-heel trend. (I wore these the night of the fateful ball. At least my feet didn’t ache like my pink cheeks did!)

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Karey! Thank you for the holiday style tips, for the fabulous product picks, and thank you most of all for making me laugh. I wish I could have attended that ball — if only for the chance to hang out with you and play dress-up for the evening.

Tell me, friends, what’s the fanciest event on your calendar this month? A work party? The Nutcracker? Maybe church on Christmas Day? Or a New Year’s Eve gathering? And have you found something to wear that you’re excited about? I’d love to hear how you like to dress up for the holidays, and where you’re headed looking so glam!

P.S. — Karey used to have a blog, but it’s archived now. I miss her writing. So I’m thinking she could borrow mine every once in a while when she has a good story or idea to share. Also, Karey mentioned Jenna Lyons. Do you know of her? She’s the Creative Director of J.Crew and she’s the coolest. One of my life goals is to have her speak at Alt Summit.