Winter Date Outfits-30 Ideas How to Dress Up for Winter Date

Winter Date Night Outfit Ideas. 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? Outfit trends bring 30 best outfit combinations to help you nail the perfect balance between gorgeous and cosy on your date this winter.

There are hundreds of wardrobe possibilities for an outfit that’ll make your special someone’s mouth drop. We’ve compiled 30 fail-safe looks along with some tried-and-true ideas that will help you look and feel like the beautiful woman that you are.

What to Wear for Your Date this Winter

Here are a few pointers to get you started:

  • Do 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 will show that the date was important enough for you to make the effort.
  • Do Consult your friends. Often, your best pals know what suits you better than you do yourself.
  • Do keep an extra jacket or scarf at hand – being practical is the new cute.
  • 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.


↓30 – 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 yourself a winning outfit for the date. Here are 22 Stylish Outfits to Wear with Long Boots This Season

Winter Date Outfits30 Ideas How to Dress Up for Winter Date



↓29 – Cute Dinner Date

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 really trending these days, so have a look at What to Wear with Printed Blazer? 24 Outfit Ideas This Year

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓28 – Classic Plaid-and-Pullover

This look is classic because it’s a simple and 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓27 – 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 be used to 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓ 26 – Bohemian Style Sweater

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, black shoes or wear a nude watch and a matching quilted or clutch. Have a look at Sweater Wearing Ideas-17 Ways to Style Sweater with Outfits

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓25 – 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 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 in your makeup. Check out these cute Maxi Skirt Outfits for Teen Girls-12 Ways to Wear Maxi Skirt

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓24 – Smart Blazer

This look is perfect for dinner or when you really want to impress someone. 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓23 – 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 colour. Add a studded black leather jacket for extra swag. For jewellery, you can wear studded bracelets and choker necklaces. Black low vamped heels are great for adding a touch of femininity to the ensemble.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓22 – 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 jewellery is a trendy way to spice up any outfit and works just as well for this one.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓21 – Slinky Red Dress

This outfit idea is perfect for the dress-loving gals. You can wear a knee-length, figure-hugging dress for your next date. If the weather is too cold, then you can wear a jacket over it along with leggings underneath your dress. As far as accessories are concerned you can wear anything in the gold color to make it look sexy. Check out 20 Cute First Date Outfit Ideas for Girls He will Love

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓20 – Extra Cozy

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 off-white color with blue jeans underneath. Wear Ugg-style snow boots to stylishly keep your feet warm. An infinity scarf is an absolute 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.
Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓19 – 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓18 – Ruched Silk Dress

Who says silk dresses are for the summers? 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓17 – 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓16 – 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 aviators will be sure to be the cherry on top.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date


↓15 – 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓14 – Dinner Date Look

This beige dress with an embellished neckline is just 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓13 – 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 comfort.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓12 – 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.

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓11 – A Touch of Flair

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

Winter Date Outfits30 Ideas How to Dress Up for Winter Date

↓10 – 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.

What to Wear on a Date

↓9 – 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.

Cute New year outfits for teens

↓8 – Funky Animal Prints

This date outfit idea is for girls who can dare to be funky. To pull off this look, you can wear hot pink skin tight jeans with leopard printed shirt tucked inside half way through. For the shoes, you may go for striking golden pumps or the classic ankle boots.

animal print dresses for first date

↓7 – 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.

how to look cute on date


↓6 – 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 silver or golden sparkly shirt tucked inside black skinny jeans. Wear a bold red lipstick and red or black high heels with this outfit look.

how to dress up for date

↓5 – Sparkling and Casual

sexy outfits for first meeting

↓4 – Floral Vibes

Floral pattern skirts are also another great option to go for when going on a date in winters. 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.

First-Date Outfit Ideas - What to Wear on a First Date

↓3 – 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 make add a little more of your quirky personality to the dress.

black outfits for date night


↓2 – 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 couldn’t feel cold if you tried in this furry puffer style jacket. Slink it over any well-tailored pants and blouse to become the picture of elegance.



↓1 – 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.



We understand that dressing right for your date can be a panicked affair, but you need to remember that through 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. Of course, it helps if you look amazing so do give this article a once-over before your next big date this winter.

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