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Happy January! It’s still quite cold here in Chicago, but that hasn’t stopped the inspiration for getting dressed up, even if I am only moving from the couch to the desk.

Headscarves: Layers are a staple in these frigid temps and I’m having fun with knit headscarves, I love these from the Verloop brand! 

Date Night Bags: For a little luxe inspiration I am channeling this Celine top handle bag, but sourcing vintage for less spendy options. 

Stirrup Leggings: Yes, the stirrup legging is back and I couldn’t be happier! I have an older Nordstrom pair already in my closet, but there are some great new options out there too. I linked a Spanx version in my recommendations! I am dreaming up ways to elevate this trend and loved this runway look from Atelin’s AW25 season. 

Knee High Boots: You have probably noticed that knee high boots are having a moment (which is probably why the legging is back in style). I’ve pulled every pair I own to the front of my closet and have been combing through eBay for gently used leather and suede options. However, I’m still on the hunt for a croc embossed version like this one from Paris Texas. I love the little micro wedge!

Wool Blazer: Last but certainly not least, a wool blazer is a cold weather MVP. Layer over a long jacket, tuck it under scarves or adorn with belts and brooches for a personalized look. The example above is from the Celine SS26 runway show and is a big inspiration with its thoughtful layering! There are so many to choose from online from new to pre-owned which makes sourcing one a breeze! 

Check out some outfit inspiration below and follow the link in this post to shop my recommendations from new to second hand. 

Outfit Inspiration with stripped sweater, leggings, coat, tall boots and leather mini bag.

Layer Up

Make the legging the statement by pairing with a cropped sweater, triangle scarf, trench coat, tall boots and a fun bag.

Pink checkard vintage blazer with black and white check wide leg pants, vintage top handle bag, tall boots and turtleneck sweater.

Play With Print

Grab a fun mini check blazer and pair with a wide leg oversized check version for a unique look. Keep underlayers to a simple turtleneck and add a fun vintage bag and tall boots for an easy outfit combo.

Oversized ski sweater with plaid maxi skirt, long scarf, bright colored bag and ballet sneakers.

Maximize Everything

Pair an oversized sweater with a maxi skirt and hooded scarf for a voluminous moment. Grab a fun bag in a pop of color and keep your shoes simple to balance the outfit.

Tight long sleeve floral printed top, wide leg fleece pants, vintage blazer, triangle scarf and short boots.

Shades Of Brown

I've been loving layering shades of browns together to add dimension to an outfit and mixing materials for texture. Recreate this with a printed top, wide leg pants, and layer your favorite vintage blazer with a wool scarf. Just add suede boots and your ready for the day!

Oversized sweater with long vintage, quilted maxi skirt, boots, skinny scarf and a Coach bag.

Embrace The Fun

One of the best things about vintage clothing is all the fun prints and textures! I am obsessed with vintage, quilted, maxi skirts and they come in a wide range of wild prints. It's important to keep the look balanced, pulling out pops of color in the print and grounding them with pieces in solid neutrals. Here I'm pairing the skirt with a solid brown sweater, brown scarf, purple crossbody bag and brown boots.

Toda Pasa T-Shirt with vintage blazer and stirrup leggings, square top handle bag and sneakers.

Monochrome Moment

This might be my favorite look in this post because it's so comfortable, easy and really versatile! Grab a great graphic tee and layer under a cool blazer. Pair that with a stirrup legging, ballet sneakers and a top handle bag and you will be ready for anything!

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