17 Trendy Winter Street Style Outfits For 2021 That You’ll Love

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This week on the Chic Pursuit I’m back with some fresh winter street style inspiration. Now that we’re officially entering the Christmas period, I’m sure that most of you will be looking for cozy jumpers, fuzzy knits and warm cardigans to wear.

We all want outfits that aren’t too fussy, because the mornings are dark and cold and it can be difficult to get out of bed, right? Well, I’ve got you covered.

I went over to some of my favorite bloggers’ Instagrams and picked out a couple of street-style outfits that have inspired me these past few weeks. As per usual, expect to see a lot of nude color schemes, but also a few outfits with bolder prints and more colorful garments.

Scroll down to see some of the best fashion blogger looks from this season, and shop the items from the links provided! Also, check out the bloggers mentioned in this post – they have some amazing content!

 

Trendy Winter Street Style Outfits To Try:

 The Over-Sized Sweater Dress

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Red sweater dress. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © ChampagneAndChanel. #winterfashion #winteroutfits #streetstyle #sweaterdress

© ChampagneAndChanel

 

 The Pop Of Color

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Pink sweater look. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © EmilyAnnGemma. #winterfashion #winteroutfits #streetstyle

© EmilyAnnGemma

 

Colorful sweaters are an easy way to make sure you stand out from the crowd. During this time of year, people tend to start hiding in black and navy clothes, but don’t be like them!

Injecting a bit of color into your wardrobe can have a huge impact on your mood too, so choose bright and joyful colors to cheep yourself up.

Bonus tip: If you can, try to co-ordinate colors in your outfit. Pair a colorful jumper with a small accessory that’s similar in color, like shoes, small bags or even nails!

 

Plaids, Plaids, Plaids

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Plaid Overalls with Over The Knee Boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © EmilyAnnGemma. #winterfashion #winteroutfits #streetstyle #overalls #plaid #overthekneeboots

© EmilyAnnGemma

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Red Plaid Skirt with Over The Knee Boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © InteriorDesignerella. #winterfashion #winteroutfits #streetstyle #plaid #overthekneeboots

© InteriorDesignerella

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Plaid Dress Look. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © JuneSixtyFive. #winterfashion #winteroutfits #streetstyle #plaid

© JuneSixtyFive

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Plaid Blazer Look. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © JuneSixtyFive. #winterfashion #winteroutfits #streetstyle #plaid #blazer

© JuneSixtyFive

 

Plaid has been such a hit this season and it’s not going anywhere! Like these bloggers show you, you can inject plaid in a number of different ways into your wardrobe.

You can be a bit more daring or get an item that will last you for many seasons, like this skirt. There’s something undeniably sexy about a plaid skirt and it keeps coming back in style year after year.

Another surefire way to get the most use out of your plaid investments is to get a plaid scarf or a plaid blazer. These are wardrobe staples that you know you can get use out of for years to come.

If you’re feeling extra splurge’y, you could even opt for the ultimate plaid scarf of all times, the Burberry check scarf.

 

The Baker Boy Lover

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Grey Sweater Dress. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © Alyson_Haley. #winterfashion #winteroutfits #streetstyle #sweaterdress

© Alyson_Haley

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Suede Skirt with Baker Boy Hat Look. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © CmCoving. #winterfashion #winteroutfits #streetstyle

© CmCoving

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: White tunic with baker boy hat and Louis Vuitton bag. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © Alyson_Haley. #winterfashion #winteroutfits #streetstyle

© Alyson_Haley

 

The Over The Knee Boots

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Ruffle top with over the knee boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © LauraBeverlin. #winterfashion #winteroutfits #streetstyle #overthekneeboots #ruffles

© LauraBeverlin

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Burgundy sweater dress with grey over the knee boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © LC_Steele. #winterfashion #winteroutfits #streetstyle #overthekneeboots #sweaterdress

© LC_Steele

 

Over the knee boots aren’t going anywhere! How else would we be able to survive cold winter weathers?!

The most popular OTK boots that fashion bloggers wear are from Stuart Weitzman, but luckily there are a few more affordable options that fit exactly the same. If you’re on a budget, check out these retailers: Marc FisherChinese Laundry and Goodnight Macaroon.

 

Detail Oriented

 

17Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Khaki pants with fringe cardigan. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © InteriorDesignerella. #winterfashion #winteroutfits #streetstyle

© InteriorDesignerella

 

The Versace Vibe

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Versace style baroque skirt. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © StylinByAylin. #winterfashion #winteroutfits #streetstyle #versace

© StylinByAylin

 

Versace might be expensive, but you can get the look for cheap. The ‘Versace look’ is now extremely in, so you’ll be able to find similar prints across the web, for example on Asos and Anthropologie.

The trend is called ‘Baroque’, so if you’re interested in finding similar items from your favorite retailer, try typing ‘baroque’ into the search bar.

 

Hat Trick

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Black sweater dress with nude wide brim wool hat and OTK boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © ChampagneAndChanel. #winterfashion #winteroutfits #streetstyle #sweaterdress #overthekneeboots

© ChampagneAndChanel

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: Mustard yellow sweater dress with nude wide brim wool hat and OTK boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © LC_Steele. #winterfashion #winteroutfits #streetstyle #sweaterdress #overthekneeboots

© LC_Steele

 

If baker boy hats aren’t really your thing, try adding a bit of elegance to your wardrobe with a wide brim wool hat.

Not only will these keep your head warm during the cold months, they will also instantly elevate any outfit that you’re wearing and THAT’S the real hat trick.

 

The Neutral One

 

17 Trendy winter street style outfits and outfit ideas to step up your game this fall and winter: White sweater dress with OTK boots. These winter street style looks are perfect to cosy up with in any urban city. Click over to the article and get inspired by more casual winter fashion looks! Image © CellaJaneBlog. #winterfashion #winteroutfits #streetstyle #sweaterdress #overthekneeboots

© CellaJaneBlog

 

Neutral outfits are always a great choice to combat winter blues! An easy but effective winter outfit is a white sweater dress with brown boots like shown here. Wearing white will make you stand out from the crowd in a major way, because almost everyone else will be wearing black and other dark colors to match the changing weather.

Which of these outfits inspired you the most? Would you be willing to copy one look from head to toe, or would you rather mix & match and create your own winter outfits? Let me know in the comments!

 

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