What I Wore Last Week: Holiday Outfit Edition

Chicago blogger shares daily outfits to wear in December over the holiday season.

Since I wasn’t posting WIWLW last year, this post is broken into two parts. The outfits I wore last week, as well as all of the holiday outfits I wore last year! I hope this post helps you find some festive outfit inspiration as you’re planning your holiday outfits over the next few weeks.

What I Wore Last Week

Chicago blogger wearing a floral jacquard blazer dress with platform heels.

My friends and I had our second annual holiday outing on Saturday night! We get dressed up in our finest party attire, go to a fancy hotel bar, and then to a very nice dinner. It’s the event I look forward to the most this time of year! So much fun. I was planning to wear the exact same thing I wore last year (see below!), but this dress I ordered for Canada ended up getting delivered on Saturday morning so I wore it instead.

Floral Blazer Dress | Sheertex Tights | Vince Camuto Platform Pumps | Amazon Earrings | Amazon Bag

Chicago lifestyle influencer Jessica Sturdy of Bows & Sequins wearing a pearl button cardigan by Abercrombie with black wide leg jeans and Chanel-esque tweed cap toe flats.

Pearl Button Cardigan | Wide Leg Jeans | Tweed Cap-Toe Flats

Chicago fashion blogger wearing a J.Crew tartan plaid maxi skirt with a green sweater for a Christmas dinner.

Ralph Lauren Crewneck Sweater | J.Crew Plaid Maxi Skirt (old; see it on the blog here) | Marc Fisher Boots | Ralph Lauren Bag (old; similar here)

Purple Faherty sweater, Citizens of Humanity Charlotte Jeans, and Loeffler Randall Leonie Dupes

Faherty Sweater | Citizens Charlotte Jeans | Sparkly Ballet Flats | Target Bag

Chicago blogger wearing a black sequin skirt with silver lug sole loafers at the Four Seasons.

Uniqlo Cashmere Turtleneck | Sequin Skirt | Opaque Tights | Silver Loafers | Hinge Cuff Bracelet | Old Navy Envelope Clutch (old; similar here)

Holiday Outfits I Wore Last Year

525 Turtleneck Sweater, Express Sequin Shorts, Black Tights, Mach & Mach Crystal Bow Platform Pump Dupes

I loved this all-black outfit with just a touch of sparkle! I thought the various textures helped break up the monochromatic outfit. I loved it with the platform party pumps, but I ended up wearing my lower slingbacks to dinner. (Shown below)

525 Turtleneck Sweater | Express Sequin Shorts | Opaque Tights | Platform Pumps | Sparkly Slingbacks | Amazon Bag

Chicago blogger wearing black sequin shorts with tights, a turtleneck, and crystal bow pumps.
Staud Sequin Mini Dress with Platform Crystal Bow Pumps

Staud Sequin Bow Back Dress | Opaque Tights | Platform Pumps

Chicago blogger wearing a festive plaid outfit for the holidays.

Ralph Lauren Crewneck Sweater | Ralph Lauren Pleated Skirt | Ralph Lauren Polo ID Bag | Lele Sadoughi Plaid Headband (old; similar here) | Ralph Lauren Tartan Flats (similar here) | Camel Coat (old; similar here + here for less) | Plaid Scarf (old; similar here)

Chicago blogger wears a holiday outfit in front of a Christmas tree. Black crystal bow going out top, straight leg jeans, crystal bow slingback heels.

Bow Front Top | Old Navy Jeans | Sparkly Slingbacks

Chicago blogger wearing a pleated top with rhinestone bow ties.

Bow-Front Top

Chicago blogger wearing a Ralph Lauren plaid midi skirt.

J.Crew Tissue Turtleneck | Ralph Lauren Plaid Midi Skirt (old; similar styles here & here) | Opaque Tights | Lugsole Booties

Chicago blogger at Ralph's Coffee in the Ralph Lauren store on Michigan Avenue.

Ralph Lauren Crewneck Sweater | Ralph Lauren Pleated Skirt | J.Crew Blackwatch Plaid Pumps (old; similar here + more below!) | Ralph Lauren Polo ID Bag | Lele Sadoughi Plaid Headband (old; similar here)

Chicago blogger wearing a plaid skirt with a Ralph Lauren dog sweater.

Ralph Lauren Dog Sweater | Ralph Lauren Plaid Midi Skirt (old; similar styles here & here) | Stuart Weitzman Sock Booties

Chicago blogger wearing a satin Petal & Pup set to a holiday party.

Petal + Pup Satin Set (sold out; similar here) | Amazon Bag

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