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What to Wear on a Casual Winter Date

Picking an outfit for a date in winter when it's nasty cold can be a real headache. Although it's easier to find the perfect outfit for a casual winter date rather than a dinner date, you still might need some inspiration. Scroll down for cute casual outfits that will keep you warm and still make you look special on your wintertime date.

How to wear: white dress shirt, navy jeans
White Dress Shirt Navy Jeans

You'll be surprised at how easy it is to pull together this casual ensemble. Just a white dress shirt paired with navy jeans.

How to wear: navy denim shirt, navy jeans
Navy Denim Shirt Navy Jeans

Consider pairing a navy denim shirt with navy jeans for a simple look that's also put together.

How to wear: white crew-neck t-shirt, multi colored floral pencil skirt, red crossbody bag
White Crew-neck T-shirt Multi colored Floral Pencil Skirt Red Crossbody Bag

If you wish take your casual style game to a new height, try pairing a white crew-neck t-shirt with a multi colored floral pencil skirt.

How to wear: black long sleeve t-shirt, yellow pencil skirt, black tote bag
Black Long Sleeve T-shirt Yellow Pencil Skirt Black Tote Bag

A black long sleeve t-shirt and a yellow pencil skirt are both versatile must-haves that will integrate nicely within your day-to-day casual repertoire.

How to wear: charcoal crew-neck sweater, grey crew-neck t-shirt, burgundy jeans, brown leopard ankle boots
Charcoal Crew-neck Sweater Grey Crew-neck T-shirt Burgundy Jeans Brown Leopard Ankle Boots Black Tote Bag

Swing into something functional yet modern with a charcoal crew-neck sweater and burgundy jeans. A chic pair of brown leopard ankle boots is a simple way to add a sense of refinement to this ensemble.

How to wear: white and black horizontal striped turtleneck, red pencil skirt, black suede lace-up ankle boots, brown leather satchel bag
White and Black Horizontal Striped Turtleneck Red Pencil Skirt Black Suede Lace-up Ankle Boots Brown Leather Satchel Bag White and Black Leopard Leather Belt

Choose a white and black horizontal striped turtleneck and a red pencil skirt if you're aiming for a sleek, stylish look. On the footwear front, this outfit pairs nicely with black suede lace-up ankle boots.

How to wear: white and black print crew-neck t-shirt, dark green midi skirt, black suede lace-up ankle boots, black leather tote bag
White and Black Print Crew-neck T-shirt Dark Green Midi Skirt Black Suede Lace-up Ankle Boots Black Leather Tote Bag

This pairing of a white and black print crew-neck t-shirt and a dark green midi skirt is extremely easy to throw together and so comfortable to work as well! Take a more refined approach with shoes and finish with a pair of black suede lace-up ankle boots.

How to wear: red coat, white and black horizontal striped crew-neck sweater, blue denim shirt, black skinny jeans
Red Coat White and Black Horizontal Striped Crew-neck Sweater Blue Denim Shirt Black Skinny Jeans Black Ankle Boots Black Tote Bag

Teaming a red coat with black skinny jeans is a wonderful option for a relaxed casual look. Complement your look with black ankle boots and ta-da: the outfit is complete.

How to wear: tobacco coat, charcoal cable sweater, navy jeans, black leather lace-up flat boots
Tobacco Coat Charcoal Cable Sweater Navy Jeans Black Leather Lace-up Flat Boots Grey Leather Clutch Grey Beanie

Rock a tobacco coat with navy jeans to put together a daily ensemble that's full of style and character. A pair of black leather lace-up flat boots instantly steps up the style factor of this ensemble.

How to wear: white boucle coat, navy skinny jeans, brown suede ankle boots, grey leather tote bag
White Boucle Coat Navy Skinny Jeans Brown Suede Ankle Boots Grey Leather Tote Bag

This pairing of a white boucle coat and navy skinny jeans is very easy to put together and so comfortable to rock a version of as well! Add a pair of brown suede ankle boots to the equation et voila, this outfit is complete.

How to wear: burgundy knit open cardigan, black crew-neck t-shirt, black skinny jeans, burgundy leather tote bag
Burgundy Knit Open Cardigan Black Crew-neck T-shirt Black Skinny Jeans Burgundy Leather Tote Bag Black Leather Belt

A burgundy knit open cardigan and black skinny jeans are a combo that every modern lady should have in her casual sartorial arsenal.

How to wear: light blue denim shirt, red plaid pencil skirt, black leather tote bag
Light Blue Denim Shirt Red Plaid Pencil Skirt Black Leather Tote Bag

This combo of a light blue denim shirt and a red plaid pencil skirt is effortless, totaly chic and extremely easy to copy!

How to wear: grey cable sweater, violet skinny jeans, grey leather knee high boots, violet leather tote bag
Grey Cable Sweater Violet Skinny Jeans Grey Leather Knee High Boots Violet Leather Tote Bag Black Suede Gloves Yellow Beanie Grey Scarf

This combination of a grey cable sweater and violet skinny jeans is an obvious choice for off duty. Let's make a bit more effort with footwear and introduce grey leather knee high boots to this outfit.

How to wear: grey oversized sweater, blue crew-neck t-shirt, blue jeans, black leather ankle boots
Grey Oversized Sweater Blue Crew-neck T-shirt Blue Jeans Black Leather Ankle Boots Black Suede Tote Bag Hot Pink Beanie

This casual combo of a grey oversized sweater and blue jeans is extremely easy to put together without a second thought, helping you look chic and ready for anything without spending too much time searching through your wardrobe. Black leather ankle boots will effortlesslly dress up even the simplest ensemble.

How to wear: white plaid coat, white crew-neck sweater, navy skinny jeans, white leather satchel bag
White Plaid Coat White Crew-neck Sweater Navy Skinny Jeans White Leather Satchel Bag Red Beanie

You'll be surprised at how easy it is to get dressed like this. Just a white plaid coat worn with navy skinny jeans.

How to wear: navy print turtleneck, light blue boyfriend jeans, black print suede ankle boots, black leather tote bag
Navy Print Turtleneck Light Blue Boyfriend Jeans Black Print Suede Ankle Boots Black Leather Tote Bag

Wear a navy print turtleneck with light blue boyfriend jeans to assemble an everyday ensemble that's full of charisma and character. And if you wish to immediately step up your ensemble with footwear, complement your outfit with a pair of black print suede ankle boots.

How to wear: black coat, navy crew-neck sweater, olive skinny jeans, green leather handbag
Black Coat Navy Crew-neck Sweater Olive Skinny Jeans Green Leather Handbag White Star Print Scarf

Infuse variation into your daily casual wardrobe with a black coat and olive skinny jeans.

How to wear: white plaid coat, white print crew-neck t-shirt, navy skinny jeans, violet leather tote bag
White Plaid Coat White Print Crew-neck T-shirt Navy Skinny Jeans Violet Leather Tote Bag Grey Beanie

For an outfit that provides function and fashion, choose a white plaid coat and navy skinny jeans.

How to wear: white coat, white and black fair isle crew-neck sweater, light blue boyfriend jeans, white leather ankle boots
White Coat White and Black Fair Isle Crew-neck Sweater Light Blue Boyfriend Jeans White Leather Ankle Boots White Leather Tote Bag Grey Beanie

If you're seeking to take your off-duty game up a notch, try teaming a white coat with light blue boyfriend jeans. White leather ankle boots are an effective way to add a hint of refinement to this ensemble.

How to wear: black print crew-neck sweater, light blue boyfriend jeans, black leather crossbody bag, green beanie
Black Print Crew-neck Sweater Light Blue Boyfriend Jeans Black Leather Crossbody Bag Green Beanie

For a casual getup with a twist, you can opt for a black print crew-neck sweater and light blue boyfriend jeans.

How to wear: camel leopard coat, white long sleeve t-shirt, blue geometric skinny jeans, black leather lace-up flat boots
Camel Leopard Coat White Long Sleeve T-shirt Blue Geometric Skinny Jeans Black Leather Lace-up Flat Boots

For a laid-back outfit with a contemporary spin, rock a camel leopard coat with blue geometric skinny jeans. Black leather lace-up flat boots are an effective way to inject an element of playfulness into your ensemble.

How to wear: navy turtleneck, burgundy skinny jeans, brown leather ankle boots, black tote bag
Navy Turtleneck Burgundy Skinny Jeans Brown Leather Ankle Boots Black Tote Bag

For a relaxed look, wear a navy turtleneck and burgundy skinny jeans — these items play really well together. When it comes to footwear, this outfit pairs really well with brown leather ankle boots.

How to wear: grey herringbone coat, black jeans, burgundy beanie
Grey Herringbone Coat Black Jeans Burgundy Beanie

A grey herringbone coat and black jeans are essential items, without which our wardrobes would feel incomplete.

How to wear: white and black horizontal striped coat, white crew-neck t-shirt, black skinny jeans, black chelsea boots
White and Black Horizontal Striped Coat White Crew-neck T-shirt Black Skinny Jeans Black Chelsea Boots Black Leather Tote Bag Black Scarf

Teaming a white and black horizontal striped coat with black skinny jeans is a savvy choice for an off-duty yet absolutely chic look. And it's a wonder how black chelsea boots can shake up an outfit.

How to wear: white and black houndstooth coat, black and white houndstooth crew-neck sweater, black leather skinny pants, black leather ankle boots
White and Black Houndstooth Coat Black and White Houndstooth Crew-neck Sweater Black Leather Skinny Pants Black Leather Ankle Boots Black Leather Satchel Bag

This pairing of a white and black houndstooth coat and black leather skinny pants is super easy to recreate and so comfortable to sport over the course of the day as well! Black leather ankle boots are a great pick to round off your outfit.

How to wear: light blue denim shirt, white and black houndstooth pencil skirt
Light Blue Denim Shirt White and Black Houndstooth Pencil Skirt

A light blue denim shirt and a white and black houndstooth pencil skirt are absolute essentials if you're planning a casual closet that holds to the highest style standards.

How to wear: camel coat, white crew-neck sweater, mustard beanie
Camel Coat White Crew-neck Sweater Mustard Beanie

This relaxed pairing of a camel coat and a white crew-neck sweater can take on different nuances depending on how you style it.

How to wear: black print crew-neck t-shirt, white skinny jeans
Black Print Crew-neck T-shirt White Skinny Jeans

For a laid-back and cool getup, wear a black print crew-neck t-shirt with white skinny jeans — these two items fit perfectly well together.

How to wear: grey print crew-neck sweater, blue skinny jeans, black leather ankle boots
Grey Print Crew-neck Sweater Blue Skinny Jeans Black Leather Ankle Boots

For chic style without the need to sacrifice on functionality, we love this combination of a grey print crew-neck sweater and blue skinny jeans. Infuse your look with an added touch of style by finishing off with a pair of black leather ankle boots.

How to wear: navy coat, charcoal cable sweater, white embroidered skinny jeans, burgundy leather clutch
Navy Coat Charcoal Cable Sweater White Embroidered Skinny Jeans Burgundy Leather Clutch

For a casual outfit, marry a navy coat with white embroidered skinny jeans — these items fit perfectly well together.

How to wear: camel coat, blue jeans, brown leather chelsea boots, grey scarf
Camel Coat Blue Jeans Brown Leather Chelsea Boots Grey Scarf

Effortlessly blurring the line between chic and casual, this pairing of a camel coat and blue jeans is bound to become your go-to. Why not add a pair of brown leather chelsea boots to the mix for a more laid-back touch?

How to wear: black turtleneck, grey polka dot pencil skirt, black leather clutch
Black Turtleneck Grey Polka Dot Pencil Skirt Black Leather Clutch

For a classic and casual getup, go for a black turtleneck and a grey polka dot pencil skirt — these two items play really well together.

How to wear: hot pink coat, light blue jeans, black leather chelsea boots, grey leopard leather clutch
Hot Pink Coat Light Blue Jeans Black Leather Chelsea Boots Grey Leopard Leather Clutch

If you enjoy relaxed dressing, marry a hot pink coat with light blue jeans. Inject a more relaxed feel into your ensemble by slipping into black leather chelsea boots.

How to wear: black coat, black skinny jeans, orange print scarf
Black Coat Black Skinny Jeans Orange Print Scarf

Go for a pared down but casually edgy outfit teaming a black coat and black skinny jeans.

How to wear: grey coat, grey turtleneck, black leather ankle boots
Grey Coat Grey Turtleneck Black Leather Ankle Boots

As you can see, looking refined doesn't require that much effort. Just make a grey coat and a grey turtleneck your outfit choice and you'll look stylish. A pair of black leather ankle boots will be the perfect complement to your ensemble.

How to wear: grey coat, white quilted crew-neck t-shirt, grey skinny pants, beige beanie
Grey Coat White Quilted Crew-neck T-shirt Grey Skinny Pants Beige Beanie

Such must-haves as a grey coat and grey skinny pants are the ideal way to infuse extra chic into your current off-duty wardrobe.

How to wear: black coat, grey crew-neck t-shirt, black leather skinny pants, black leather ankle boots
Black Coat Grey Crew-neck T-shirt Black Leather Skinny Pants Black Leather Ankle Boots Black Leather Crossbody Bag Orange Scarf

A black coat and black leather skinny pants worn together are a total eye candy for those who appreciate refined getups. Black leather ankle boots work amazingly well with this ensemble.

How to wear: black shearling coat, charcoal crew-neck t-shirt, navy skinny jeans, black leather lace-up flat boots
Black Shearling Coat Charcoal Crew-neck T-shirt Navy Skinny Jeans Black Leather Lace-up Flat Boots Black Leather Tote Bag Red Plaid Scarf

You're looking at the definitive proof that a black shearling coat and navy skinny jeans are awesome together in a relaxed getup. When this look appears too fancy, play it down by rounding off with black leather lace-up flat boots.

How to wear: navy puffer jacket, black embellished crew-neck sweater, black leather skinny pants, black leather ankle boots
Navy Puffer Jacket Black Embellished Crew-neck Sweater Black Leather Skinny Pants Black Leather Ankle Boots Black Leather Crossbody Bag

Try teaming a navy puffer jacket with black leather skinny pants to pull together a stylish getup. Get a bit experimental when it comes to shoes and class up this look by rounding off with black leather ankle boots.

How to wear: olive parka, black crew-neck sweater, black leather pencil skirt, black leather lace-up flat boots
Olive Parka Black Crew-neck Sweater Black Leather Pencil Skirt Black Leather Lace-up Flat Boots

This laid-back pairing of an olive parka and a black leather pencil skirt is extremely easy to put together in no time, helping you look chic and prepared for anything without spending a ton of time searching through your wardrobe. Does this outfit feel all-too-polished? Invite a pair of black leather lace-up flat boots to shake things up.

How to wear: red coat, white dress shirt, navy skinny jeans, black suede over the knee boots
Red Coat White Dress Shirt Navy Skinny Jeans Black Suede Over The Knee Boots Black Leather Crossbody Bag Black Leather Belt

A red coat and navy skinny jeans matched together are such a dreamy look for women who appreciate off-duty styles. On the footwear front, this getup is rounded off well with black suede over the knee boots.

How to wear: light blue coat, beige crew-neck sweater, white skinny jeans, pink leather ankle boots
Light Blue Coat Beige Crew-neck Sweater White Skinny Jeans Pink Leather Ankle Boots

Exhibit your styling chops in this casual pairing of a light blue coat and white skinny jeans. A pair of pink leather ankle boots can integrate smoothly within a multitude of ensembles.

How to wear: black coat, navy jeans, black leather ankle boots, grey scarf
Black Coat Navy Jeans Black Leather Ankle Boots Grey Scarf

Combining a black coat with navy jeans is an on-point idea for a laid-back yet chic outfit. Black leather ankle boots are a nice choice to complete this ensemble.

How to wear: black leather puffer jacket, black cardigan, black skinny pants, black print clutch
Black Leather Puffer Jacket Black Cardigan Black Skinny Pants Black Print Clutch Black Belt

A black leather puffer jacket and black skinny pants are the perfect way to inject extra cool into your current styling collection.

How to wear: grey coat, white print crew-neck t-shirt, navy skinny jeans, tan suede lace-up flat boots
Grey Coat White Print Crew-neck T-shirt Navy Skinny Jeans Tan Suede Lace-up Flat Boots

This pairing of a grey coat and navy skinny jeans is a safe and very fashionable bet. You could perhaps get a bit experimental with footwear and slip into a pair of tan suede lace-up flat boots.

How to wear: green crew-neck sweater, white crew-neck t-shirt, silver pencil skirt, gold clutch
Green Crew-neck Sweater White Crew-neck T-shirt Silver Pencil Skirt Gold Clutch

A green crew-neck sweater and a silver pencil skirt are a great combo worth integrating into your day-to-day casual repertoire.

How to wear: charcoal print crew-neck t-shirt, black skinny jeans, black leather lace-up flat boots, black leather crossbody bag
Charcoal Print Crew-neck T-shirt Black Skinny Jeans Black Leather Lace-up Flat Boots Black Leather Crossbody Bag

Choose a charcoal print crew-neck t-shirt and black skinny jeans for a simple ensemble that's also put together. If in doubt about what to wear in the shoe department, stick to a pair of black leather lace-up flat boots.

How to wear: black and white print crew-neck sweater, white pleated midi skirt
Black and White Print Crew-neck Sweater White Pleated Midi Skirt

Dial it down a notch in this comfy pairing of a black and white print crew-neck sweater and a white pleated midi skirt.