35 Cute Winter Date Outfit Ideas & Styling Tips

Ah, the date night. After hours of giggling with your girlfriends and waiting in anticipation, the day is finally here. No matter what stage of the relationship you’re in, wearing just that right outfit can often feel like a mission impossible.

Throw in the winter chills and you’ve got another dilemma: to look hot or keep warm? We say – why not both?

In our last post, we talked about some influencer-inspired winter outfits but today we’ll be focusing on the more natural, practical winter date outfits. The aim of course is to help you nail the perfect balance between gorgeous and cosy on your date this winter:

What to Wear for a Winter Date?

Here are a few pointers to get you started:

  • Go for a little shopping spree – if you can afford it. A little can go a long way. Something as simple as a new scarf or top will show that the date was important enough for you to make the effort.
35 Cute Winter Date Outfit Ideas & Styling Tips
  • Do Consult your friends. Often, your best pals know what suits you better than you do yourself.
35 Cute Winter Date Outfit Ideas & Styling Tips
  • Do keep an extra jacket or scarf at hand – being practical is the new cute.
35 Cute Winter Date Outfit Ideas & Styling Tips
  • Don’t wear something that makes you feel uncomfortable. An outfit will only shine if you feel good in it.
  • Don’t over-accessorize – unless the situation calls for it. In most cases, though, less is more. Too much bling can make you look tacky.
35 Cute Winter Date Outfit Ideas & Styling Tips

Outfit Ideas

35 – Casual Black Sweater

People often limit sweaters to their ‘at-home’ wardrobes, but you can easily style your black sweater over virtually any cocktail dress and convert it into a cute skirt.

Throw in some knee-high boots, and you’ve got a winning outfit for the date. Here are some more Stylish Outfits to Wear with Long Boots.

35 Cute Winter Date Outfit Ideas & Styling Tips

34 – Blazer

Dinner Dates call for something a bit more formal, so bring out your lacy pink dress and top it with a blazer to keep yourself comfortably warm.

A jacket and a blazer are both ideal for layering as they keep you warm without making you look bulky.

Printed blazers, in particular, are trending these days, so have a look at my guide on What to Wear with Printed Blazer.

35 Cute Winter Date Outfit Ideas & Styling Tips

33 – Classic Plaid-and-Pullover

This look is classic because it has a straightforward appeal.

If you want, you can glam up the look with a chunky statement necklace and boots to die for.

For casual dates, it’s important to wear soft, natural makeup. Let your hair down in loose waves or a messy hairdo.

35 Cute Winter Date Outfit Ideas & Styling Tips

32 – Put on a Cute Jacket

Layering is the magic word to solve all your winter wardrobe problems, and it applies to dates as well.

A cropped jacket can freshen up your dress and keep your shoulders safe from the chills.

With the right accessories, you can make this look for a dinner and just as well for a movie date. This would be a really cute outfit for teen girls.

35 Cute Winter Date Outfit Ideas & Styling Tips

31 – Bohemian Look

The boho-chic style is THE style to keep an eye out for this year.

This outfit is elegant and super easy to recreate. All you will need is black skin-tight jeans, and pair them up with any printed loose sweater.

For accessories, you can add as many as you want.

You can go for a black scarf or black shoes or wear a nude watch and a matching quilted or clutch. Have a look at these Sweater Wearing Ideas for more tips.

35 Cute Winter Date Outfit Ideas & Styling Tips

30 – Simple Box-Plait Skirt

For a semi-formal occasion, you can wear any coral or nude-colored knee-length skirt.

With this skirt you can wear a white lace skirt tucked in or out.

For accessories, strap on some nude espadrilles and a messenger bag.

An advantage to wearing corals is that you can easily incorporate the shades into your makeup.

35 Cute Winter Date Outfit Ideas & Styling Tips

29 – Smart Blazer

This look is perfect if you want a preppy look.

You can pair it with a blazer, but be sure that the blazer is well-tailored so that it fits you in all the right places.

Sloppy tailoring is arguably the least attractive way to dress unless you’re going for an intentionally oversized look.

35 Cute Winter Date Outfit Ideas & Styling Tips

28 – Biker girl style

Not all girls are comfortable in a dress or skirt, and they don’t have to be.

Again, how you feel about your outfit is more important than anything else.

You can wear black skinny jeans with a shirt in a contrasting color.

Add a studded black leather jacket for extra swag. For jewelry, you can wear studded bracelets and choker necklaces. Black, low-vamped heels are great for adding a touch of femininity to the ensemble.

35 Cute Winter Date Outfit Ideas & Styling Tips

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27 – Stripe It Up

Little pops of patterns can bring your outfit to life.

Take, for example, the ensemble below.

A simple striped shirt with a bold red jacket and cutwork skirt.

This outfit is really versatile and is a great option if your date is keeping the plan as a surprise. High-heeled boots are all you need to really get the winter outfit into shape. Chunky jewelry is a trendy way to spice up any outfit and works just as well for this one.

35 Cute Winter Date Outfit Ideas & Styling Tips

26 – Red Dress

This outfit idea is perfect for the dress-loving gals.

You can wear a knee-length, red sweater dress for your next date. If the weather is too cold, then you can wear leggings underneath your dress.

As far as accessories are concerned, you can wear anything in the gold color to make it look sexy.

35 Cute Winter Date Outfit Ideas & Styling Tips

RED QUARTER ZIP SWEATER MINI DRESS $48

RED TURTLENECK SWEATER DRESS (SIMILAR) $48

SANDSTONE COLORED KNEE HIGH BOOTS

25 – Extra Cozy for Coffee Date

One does simply not complete a winter outfit without a cup of steaming Starbucks coffee.

For this dressing style, you can wear a loose sweater in an off-white color (or any other pastel shade) with blue jeans underneath.

Wear Ugg-style snow boots to stylishly keep your feet warm.

An infinity scarf is a must-have for this season and goes great with sweaters. 

For accessories, try to keep the color tones cool and neutral, for example, shades of nude or light brown.

35 Cute Winter Date Outfit Ideas & Styling Tips

24 – Strawberry Affair

Strawberry red goes great with any skin color and better suits the winter season than its warmer counterparts.

This printed dress, for example, looks great with a black jacket and can even be worn over jeans or stockings, depending on the formality of your date.

35 Cute Winter Date Outfit Ideas & Styling Tips

23 – Ruched Silk Dress

Who says silk dresses are for the summer?

Throw on a leather jacket to create a fusion of styles and really impress your date. Dangling earrings and heels can add a formal element to your ensemble.

This look is especially fun to recreate because of its vast possibilities.

35 Cute Winter Date Outfit Ideas & Styling Tips

22 – Sequined Glam

Sequins will never go out of style. This look works especially well if your date is going to be in a low-light setting, say, a club or a cozy restaurant.

You can spice up your dress with a belt or a furry shrug to channel your inner queen.

35 Cute Winter Date Outfit Ideas & Styling Tips

21 – Preppy Shirt

This fresh schoolgirl look is great for girls who are not afraid to show how smart they are.

The lacy fabric of the skirt can be a welcome update to the classic look. A bold red lip and black aviator sunglasses will surely be the cherry on top.

35 Cute Winter Date Outfit Ideas & Styling Tips

20 – Smart Pencil Skirt

Pencil skirts are a great way to highlight your legs. For dates, especially first dates, it’s best not to bare it all, rather use selective focus to make your favorite assets stand out.

This outfit pairs a lime yellow skirt with a contrasting purple cardigan and blouse. A slim belt and simple jewelry can really enhance your outfit.

35 Cute Winter Date Outfit Ideas & Styling Tips

19 – Dinner Date Look

This beige dress with an embellished neckline is sparkly enough to keep things interesting.

There may be certain elements to date you can’t ensure to be successful, but a minimalist dress like this is a sure winner. Create a messy side bun to complement the dress.

35 Cute Winter Date Outfit Ideas & Styling Tips

18 – Simply Chic

Sequins can be adjusted easily into casual wear, for instance, this cream-colored blouse goes great with the champagne gold sequins in the skirt to make you look effortlessly sophisticated.

You can pull off wearing the skirt with stockings or leggings for added comfort.

35 Cute Winter Date Outfit Ideas & Styling Tips

17 – B&W

The bestest friends in history: black and white. These colors used together are the instant recipe for making you look totally in control, which is great if you, too, turn into a nervous mess sometimes before a big date.

35 Cute Winter Date Outfit Ideas & Styling Tips

16 – A Touch of Flair

Sculptured silhouettes are no longer limited to high fashion. This peplum top with a sculptured flair is nothing short of inspiring.

35 Cute Winter Date Outfit Ideas & Styling Tips

15 – Simple Dress with a Cinched Waist

This simple knee-length dress with a belt gives off major cowgirl vibes and makes it look like you’re not trying too hard to look as good as you do. Grab a gorgeous handbag to finish off the look.

35 Cute Winter Date Outfit Ideas & Styling Tips

14 – For an Extra Glamorous Night

This super glittery strapless dress can be worn over jeggings and would go great with a shrug or cropped jacket, too. The dangling gold earrings together will create a perfect look, especially if you’re gonna be dancing.

35 Cute Winter Date Outfit Ideas & Styling Tips

13 – Funky Animal Prints

To pull off this look, you can wear hot pink skin-tight jeans with a leopard printed shirt tucked inside halfway through. For the shoes, you may go for striking golden pumps or classic ankle boots.

35 Cute Winter Date Outfit Ideas & Styling Tips

12 – High-waisted Skirt and Blouse

A white blouse is great if you don’t want to give too much about yourself away, especially for first dates.

The high-waisted mini skirt and belt will complete a striking look. You can also top the blouse with a snug vest to play it safe in this weather.

35 Cute Winter Date Outfit Ideas & Styling Tips

11 – All that Glitters

Is definitely gold. You can wear a sparkly shirt if you are a sparkle and sequence lover.

For this style, you can wear a silver or golden sparkly shirt tucked inside black skinny jeans. Wear bold red lipstick and red or black high heels with this outfit look.

35 Cute Winter Date Outfit Ideas & Styling Tips

10 – Sparkling but Casual

35 Cute Winter Date Outfit Ideas & Styling Tips

9 – Floral Vibes

Floral pattern skirts are also another great option to go for when going on a date in winter. You can wear it with black and white striped shirt, either tucked in or not.

This combo of feminine and masculine patterns is perfect if you are planning to go for a decent lunch or dinner on your date.

35 Cute Winter Date Outfit Ideas & Styling Tips

8 – Little Black Dress

Chanel was on to something when she started this trend. The LBD is going as strong as ever and works great for girls who like to keep things simple.

Gorgeous red boots and a matching fedora will add a little more of your quirky personality to the dress.

35 Cute Winter Date Outfit Ideas & Styling Tips

7 – Furry Puffer Jacket

If you’re one of those gals who are hesitant to step out because of how cold it is, this look is just for you. You won’t feel cold even if you try, in this furry puffer-style jacket.

Slink it over any well-tailored pants and blouse to become the picture of elegance.

35 Cute Winter Date Outfit Ideas & Styling Tips

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6 – Suit Up

As the fashion world grows more and more inclusive by the day, you can simply don a pinstriped suit over your favorite T-shirt to create a look that shows you are creative and way worth his interest.

Complete the style with a sporty ponytail and sneakers.

35 Cute Winter Date Outfit Ideas & Styling Tips

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We understand that dressing right for your date can be a panicked affair, but you need to remember that although your dressing is undoubtedly fabulous, it is you who has won the date and not your fashionable attire. If your date is ‘the one’, then you’ll look appealing no matter what you wear – as long as you’re you.

Celebrity Style

Below, we look at how some of our favorite celebs are dressing up this Winter. We’ve specifically chosen the outfits that we feel would be great for date nights (or days).

But if you want a summary, here are some common trends we observed when looking at their Winter date looks:

  • Lots of focus is on neutral colors and black.
  • Lots of leather elements.
  • Oversized fits.
  • Minimalist Accessories (sunglasses were seen A LOT).
  • Boots seem to be the most popular type of shows.

5 – Hailey Beiber in Denim Dungarees and a Long, Oversized Black Coat

35 Cute Winter Date Outfit Ideas & Styling Tips

Denim dungarees (similar)

Long black coat (similar but in leather)

4 – Kendall Jenner in Black Tank Top, Matching Trousers and a Cherry Red Sweater for Concert Date

35 Cute Winter Date Outfit Ideas & Styling Tips

3 – Gigi Hadid in a Button Up Cardigan and Matching Knee High Boots for Dinner Date with Bradley Cooper

35 Cute Winter Date Outfit Ideas & Styling Tips

Black tall boots (similar)

2 – Zendaya in a Silky Slip Dress and Contrasting Camel Colored Trench Coat for a Romantic Dinner Date in London

35 Cute Winter Date Outfit Ideas & Styling Tips

1 – Avril Lavigne in an All Black Fit

35 Cute Winter Date Outfit Ideas & Styling Tips

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