Fashion

Not Sure What to Wear on a Winter Date? Steal These Outfit Ideas From Kemper Baugh

Published by
Rachel Aschenbrand-Robinson

Click to shop
Figuring out what to wear on a date can be tricky at any time of year, but in winter it’s especially challenging. After all, it’s hard to feel flirty when the weather calls for covering up. But shivering in an unseasonable ensemble isn’t exactly cute, either, so incorporating cold-weather staples into your winter date outfits is a must.

So how do you work sweaters, boots, puffer jackets, and the like into your date looks without sacrificing your style? Just ask Insta-babe Kemper Baugh of @joandkemp. Ahead, the longtime Lulus babe–and partner on our first-ever influencer edit–is sharing her tips and outfit ideas for winter date dressing, and well, the chilly season never looked so hot.

Shacket + Knit Bodycon Dress + Knee-High Boots + Hoop Earrings

Click to shop
“For a date night, I love to layer. That way, you can shed pieces according to the weather,” says Kemper. A shacket is a wardrobe must-have when it comes to layering, and this plaid style lends a laid-back vibe to an otherwise vampy look. You can wear it over your ribbed knit dress, tie it around the waist, or drape it over your shoulders–who doesn’t love outfit options? Tall boots mean you’re only showing a little bit of leg–and they leave room for a stylish pair of tights to peek out if you choose.

Cowl Neck Sweater + Vegan Leather Skirt + Mid-Calf Boots + Small Sunglasses

Click to shop
“Cold weather outfits are some of my favorites because you can style them so many different ways,” Kemper notes. Case in point: A boxy cropped sweater looks great tucked into a vegan leather skirt, untucked, or even layered over a bodycon dress. Sock-style mid-calf boots only add to the cozy-sexy vibe.

Velvet Bodycon Dress + High Heel Sandals + Hoop Earrings

Click to shop
For party season, a velvet bodycon dress is both sexy and seasonal. This festive pick is perfect for a holiday fete, a winter wedding, or another special occasion that calls for cocktail dressing. Strappy high heel sandals keep the look semi-formal, but feel free to try it with high boots and a cropped jacket!

Cropped Puffer Jacket + Crop Top + High-Waisted Jeans + Mid-Calf Boots

Click to shop
Crop tops in winter? Hell yes. “A cropped sweater or top with jeans or trousers, boots, and a coat is an ideal look I would typically go for,” says Kemper. A teeny top and cropped puffer balance out high-waisted jeans–and make a perfect combo for moving seamlessly between the cold outdoors and heated indoor spaces.

Knit Bodycon Dress + Knee-High Boots

Click to shop
According to Kemper, “A dress or skirt with knee-high boots is a fun, spunky option for winter.” Wearing a long-sleeve knit dress with tall boots will keep you both comfy and cute, which is always the goal, right? For extra chilly days, a statement coat or jacket adds another layer of style.

We want to see your winter date outfits! Show us how you look cute in the cold on Instagram @lulus using #lovelulus–and shop the @joankemp Edit for more picks you can wear from fall through winter!

Recent Posts

  • Fashion

Coastal Outfit Ideas: The Best Dresses for a Seaside Escape

Blue skies, salty air, sun-warmed boardwalks, and a suitcase full of cute dresses: coastal summer…

7 hours ago
  • Fashion

21 Cute Concert Outfit Ideas: Style Inspo for Every Type of Show

Choosing the perfect concert outfit, whether it’s for an arena show, a music festival, or…

6 days ago
  • Fashion

Wedding Guest Guide: What to Wear When the Invite Says Black Tie Optional

As a guest at a wedding, you want to dress your best to celebrate the…

2 weeks ago
  • Fashion

These Are the Summer Dresses You Should Own in 2026, According to Lulus Girlies

We’re kind of always dress shopping, but summer is when it really hits. The options…

4 weeks ago
  • Fashion

What To Wear To A Beach Wedding: The Complete Guest Attire Guide

Beach weddings are some of the most fun nuptials to attend–the ocean breeze, the vacation…

4 weeks ago
  • Fashion

What to Wear on a Beach Vacation: 16 Outfits to Put You in a Getaway Mood for 2026

Packing for a warm-weather trip means striking the right balance between comfortable and chic, and…

1 month ago