What to Wear on a Coffee Date in Winter

If you’re back on the dating scene after many years away, you’re probably finding that dating after 40 is stressful, and figuring out what to wear only adds to the challenge!

Winter dates have a certain charm. Something about the cold weather makes a casual meet-up at a coffee shop feel cozy. The warm coffee aroma, and relaxed vibe make it the perfect setting for a date.

The key to a great winter date outfit?  Style, plus warmth.  You don’t want to feel all buttoned up and frumpy, but you don’t want to be chilly either. I always say that for women over 40, 50+,  looking fabulous is all about timeless classics with a modern twist. And when you’re dating,  it doesn’t hurt to throw in a touch of playful allure, too!

I’ve put together some cute, chic, and cozy winter coffee date ideas. Let’s find your look.

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What to Wear on a Coffee Date in Winter

You may want to wear a casual skirt or sweaterdress with tights to stay warm, but your favorite jeans or stretchy pants are more likely. Since you’ll be making an entrance and then sitting down, I’m going to concentrate on what really matters—what to wear up top.

A Relaxed, Beautiful Top and Classy Coat

When it comes to tops, you have many choices. You can wear anything from a soft, cozy sweater to a pretty flowy blouse, a cute tee with a long or short cardigan, a relaxed jacket, or a layered top look.

Your coat depends on your style personality, but a beautiful wool-blended coat, long or short, is always very classy for a winter coffee date.

Romantic and Alluring Colors

Colorwise, go right ahead and wear the colors you like and feel confident in. However, if you want to give off some feminine energy, think soft pastels and neutrals. Pink, blush, cream, light blue, soft yellow, and taupe are romantic and feminine. Or, wear colorful brights. Vibrant hues like hot pink, fuschia, aqua, purple, and red are perky and sexy.

Attractive Necklines

While chatting with your date, he’ll be focused on your face and neckline, so choose a top that highlights these areas. A V-neckline or scoop neck is elegant, slimming, and alluring, while a loose cowl neckline is soft and sensuous.

An off-the-shoulder top like this pretty blue off the shoulder sweater is sweet and a little flirty, and an open-collared neckline like a button-up shirt or polo sweater is face-framing and sporty. A sleek ribbed mock neck sweater with some shiny buttons at the neck can also look nice.

Inviting Fabrics

Soft, sensuous winter fabrics are also perfect for a winter date outfit. For example, a baby-soft, eyelash sweater is much more romantic than a thick, boxy brown crew neck cable knit sweater. However, make that cable knit sweater white,  softer and relaxed with a wide v-neck, and it suddenly becomes more feminine.

Other winter fabrics that look like you want to touch them are anything silky (like satin) or cozy textured fabrics like boucle, velvet, and buttery suede. Leather is on the sexy side (i.e., faux leather fleece leggings or a leather jacket) and can be woven into a winter date outfit if that is more your style.

Feminine Details

This beautiful pink sweater will bring a glow to your face, and the pretty silver buttons make it feel special for a casual coffee date. Embellished pieces like a jeweled belt, a zipper-front sweater, or any kind of top with feminine detail are great, too. I love the dainty rosettes on this classic sweater below.

Beautiful Accessories

Leather gloves, a classy cashmere scarf, chic boots, or booties will round off your winter coffee date outfit. For jewelry, looser, dangly necklaces and earrings, such as hoops or small drop earrings, are alluring.

Chic Ankle or Knee-High Boots

 Ankle boots and knee-high boots are perfect for a coffee date and will keep your feet warmer than trying to wear shoes in winter. Bonus points if they’re suede!

Stay Stylish and Warm in These Winter Coffee Date Outfits

Effortlessly Feminine

This outfit strikes the perfect balance between sexy and elegant for coffee dates when you want to look a little more dressed up. This gorgeous belted hip-length coat is super figure-flattering and looks great with a matching V-neck top and jeans. The chunky statement necklaces give this outfit a glam vibe.

Classic and Chic

For my classic gals, this is a lovely coffee date outfit.  Pair this elegant burgundy lady cardigan with the same-color tank to create a relaxed but polished tone-on-tone look. Animal print slingbacks add that shot of excitement you want for a first date. 

Modern Casual and Cool

A cozy cashmere sweater is perfect for a coffee date. It feels luxurious, looks gorgeous, and is like a warm hug.  It’s worth every penny! You can find cashmere sweaters in almost any color, but I really like this floral-print cashmere sweater from Talbots. They are super soft and feminine. To look warm and approachable, throw on a cozy boucle jacket. These trendy colors make the look modern and youthful.

Cozy Layers

Layers are your friend on chilly days, but you don’t want to look bulked up. The key is to wear fine layers. Try wearing a thin cashmere sweater with a lightweight, relaxed blazer. Add jeans, a cute belt, and some statement jewelry for a little pizzazz!

Slim-fit turtlenecks also make great layering pieces. 

Color Pop

In the season of dark neutrals, it can be fun to add some color back into your wardrobe! This jewel-toned purple car coat pairs beautifully with this silky satin button-up, jeans, and a stunning embellished belt. It makes for a fabulous, casually chic winter date outfit!

The Last Word

Figuring out what to wear on a first date in your 40s, or even just a simple coffee date, can be intimidating, especially if you’re dressing for the wintertime. The key is finding pieces that prioritize style, comfort, and warmth. And, of course, wear outfits that make you feel age-amazing! As long as you feel confident, you’re unstoppable.

Which looks are you excited to wear on your winter coffee date?

Visit my LTK shop to see my favorite winter wardrobe pieces. You can also join my private Facebook group, Fabulous After 40 Dressing Room, to discuss the fabulous winter date outfits you’re putting together this season.