Winter Date Night Outfits

Winter doesn’t mean ditching dresses. It’s all about styling them to suit the weather, destination and vibe.

See the colder seasons as an opportunity to play with different silhouettes or prints you wouldn’t typically wear in summer. You’ll be surprised by all the different ways your winter dresses can be worn when the temp drops!

What we’re loving:

• Go for long sleeve dresses with fluted or bell sleeves, an open back, or off-shoulder details for an effortlessly romantic vibe
• Ribbed or knit fabrics and fun patterns like stripes, polka dots, or checks
• Coats or oversized faux leather jackets for cool girl energy
• Polka dots, deep V-necks, and midi lengths are key if you’re after something timeless and chic

Cold weather is the perfect excuse to elevate your top game. The right long sleeve or knit can take you from casual everyday vibes to elevated in seconds.

What we’re loving:

• Long sleeve fitted tops in lace or sheer fabrics are super flattering and perfect for winter date nights
• Try cinched waists, off-shoulder styles, or slouchy knits for a cozy-but-chic look
• Don’t forget elevated knitwear! Fine knits and sweaters with feminine details instantly dress up your denim or mini

Spend a little extra time curating your winter bottoms and your date night getting ready routine instantly becomes easier. From timeless denim to statement minis, this season is all about mixing shapes and layering versatile pieces.

Here’s what we’re loving:

• Jeans! Go for dark or mid-blue washes in bootcut or wide leg fits. These pair perfectly with a pointed boot peeking out the bottom.
• Wide leg pants with belt, stud, or eyelet details will add an edge to your look
• Mini skirts in faux leather, faux suede, or plaid, layered over sheer tights with tall boots. Pair with a staple black long sleeve and a jacket to complete the look. This is your sign to keep your mini skirts in your rotation for cute winter looks!

Matching sets make everything easier. Effortlessly get dressed before your date without thinking more than one minute about your outfit.

What we’re loving:

• Knit cardi and shorts sets look super chic paired with loafers and a coat
• Polka dot matching sets are a fave right now, especially for romantic dinner dates
• Elevated maxi skirt sets in ribbed or soft fabrics are another dreamy winter option!

Outerwear is the finishing touch that pulls your entire look together. Think of your jacket or coat as the statement piece that takes your outfit from cute to chic.

What we’re loving:

• Faux suede bombers are the jacket of the season
• Oversized faux leather jackets will be the most reliable layer in your wardrobe, definitely a must-have!
• Long-line coats are timeless and chic, perfect for staying warm while looking elevated

Accessories are the cheat code to adding an elevated touch to any outfit. They bring personality and texture without taking up much of your getting ready time.

• Jewelry: Think stacked resin bracelets worn over long sleeves, chunky rings, or statement earrings
• Bags: Go for slouchy faux suede or faux leather styles with fun details like studs or eyelets
• Hats: A fluffy hat or beanie adds a playful (and practical) touch if your date’s outdoors

Unless you’re cozying up for a movie date indoors, you’ll need a cute pair of shoes to complete your look. From sleek boots to preppy loafers, the right pair can make or break your OOTN.

• Boots: A black heeled pair is a must. Ankle or mid-calf styles work perfectly under jeans, while knee high boots pair effortlessly with minis
• Loafers or ballet flats are our top pick for casual dates. Cute, comfy, and versatile, you’ll wear these on the daily too!
• Hot tip from our Global Styling Director, Char: “Pair tall boots with sheer tights and a mini skirt. It’s one of the most flattering silhouettes and our go-to look for winter date nights.”