What’s Your Holiday Style: Casual or Dressy? (Plus, a Big Sale)

How do you like to dress for the holidays? Do you prefer feeling cozy or going all out? Madewell has gorgeous pieces, so here are a few picks for both approaches…

This silk top is what my 10-year-old self imagined I’d wear as a grown up, hosting dinner parties and swooping into rooms with glasses of bubbly. Now that I am grown up, I still find the look effortlessly chic and would love to wear it on repeat this season. For something more laid-back, how great is this checked sweater with contrasting stripes?

If you’re going for sexy and slinky, this number feels straight out of Bond movie. That wine red is just so good. Or, if you’d rather feel wrapped in a blanket, pull on this V-neck cardigan, which has just the right amount of slouch and comes in seven colors.

How flirty yet easygoing is a slip skirt? I’d like to wear one to our Friendsgiving dinner with pearl earrings and a French hair pin. For a movie night, a pair of ’90s jeans would be comfy for cuddling on the sofa, along with a crinkled shirt and ballet flats.

Silver slingbacks are a fun way to be part of the metallics trend, which is huge right now. Wouldn’t you love to wear them while eating dessert at the bar of a fancy restaurant? If you’re team flats, I’d recommend these velvet cuties. They’re sweet and charming and come in six colors (including silver!).

One holiday accessory that brightens any ensemble — even trusty sweatpants — is a pair of crystal earrings. I’m also a sucker for a red bag (I’ve worn one for years), so I’m loving the pop of this bucket tote.

Finally, for outerwear, a classic peacoat feels elegant for work meetings, dinner dates or holiday parties. Or if your favorite winter ritual is taking long, rosy-cheeked walks (the fresh air feels so good!), or leaning into other outdoorsy activities, go with a quilted puffer in red or blue.

Great news: Madewell is having a huge sale right now. Use the code LETSGO for 40% off your purchase, good until November 22nd. Exclusions apply. See everything here, including a shawl jacket for traveling and a million excellent gift ideas.

(This post is sponsored by Madewell, a brand we have loved and worn for many years. Thank you for supporting the brands that support Cup of Jo.)