Style - February 11, 2020

25 Winter Outfit Ideas

Hi y’all! Hope you’re having a good start to your week :) I’m over here freezing in Denver but I think I’m slowly kinda sorta getting used to the weather (and snow!). Mid-Februrary is always that time of year when I start to get BORED with my winter outfits and basically winter in general. There are only so many boots and jackets you can wear, ya know?

Now that I live in a city that truly gets winter, it’s been a bit easier slash more fun this year, but I’m still hitting a rut. Over the weekend I spent some time looking on Pinterest and older outfits of mine to inspire me. I thought I’d share 25 of those looks with y’all in case you’re hitting a wall too. Hope it’s helpful!

Winter Outfit Ideas

1. Winter Outfit with a Classic Trench Coat

winter outfit idea business casual, white turtleneck, black booties, Hermes belt, camel trench coat

Outfit Details: Trench Coat (wearing size XS) // Turtleneck // High-Waisted Jeans (I’m wearing size 25 Short) // Booties

Have y’al noticed I’ve been really into turtlenecks lately? I’ve mostly been styling my black one but I recently got a white one and I’ve been loving the lighter option!

2. Winter Outfit Idea: Try Mixing Two Neutral Prints

Outfit Details: Striped Tissue Turtleneck (wearing size XS) // AgoldE high-waisted jeans // Madewell leopard booties // BB Dakota sherpa jacket (wearing size XS)

I absolutely love mixing prints! And I think that mixing leopard with stripes is always a winning combo! I loved how well these stripes paired with the color of this jacket and that the booties complemented the browns perfectly!

3. An Oversized Tunic and Faux Leather Leggings

faux leather leggings, tunic sweater, printed beanie, marc fisher snow boats, casual cute winter outfit

Outfit Details: Oversized Cream Sweater (sold out) // faux leather leggings (I wear size small) // Marc Fisher Lace Up Booties

You really can’t go wrong with an oversized tunic and leather leggings if you ask me! It’s literally one of my GO-TO winter outfits! I really think these faux leather leggings are some of the most comfortable and warmest options I have in my winter wardrobe – I LOVE them! I love how easy they are to dress up and down too!

4. Shorts and Tights with a Blazer

winter outfit leather paper bag shorts tights combat boots with blazer and turtleneck

Outfit Details: Leather shorts // Black Turtleneck // Blazer (old – similar) // Combat Boots

I haven’t had the chance to shoot this look yet, but HOW CUTE is this combo?! It’s certainly a little out fo my comfort zone but I think that’s why I love it. Like I said, I’m REALLY trying to challenge myself to wear all different sorts of combos for winter outfits and figure out how to make them warm! What do you think about this? Would you wear it?

5. Wide Leg Jeans & Booties

cute winter outfit idea, neutral stripe sweater, Levi's wedgie jeans, monclear jacket

Outfit Details: Sweater ($99 – wearing size XS) // Jeans // Cream leather Booties // Moncler Jacket (wearing size 3)

These exact jeans aren’t available anymore – they’re from several years ago! But I linked a similar pair above. Lately, I’ve been having fun trying different tall shaft booties with wide leg jeans. I love the casual, laid-back look the combo gives your outfit! If you want some inspiration/tips on how to wear jeans with booties, you should check out my how to wear booties blog post if you haven’t already!

winter outfit, corduroy coat, black tee, white booties

Outfit Details: Black crewneck, long-sleeved tee (such a good basic!) // AgoldE Riley High-waisted jeans // Booties // Coat (wearing size US2) // Sunglasses // Missoma Chain Necklace // Missoma pendant necklace

I’ve been wearing these jeans on repeat this season! The ones I have area actually the double pocket ones, but they’re sold out most places. The important thing is that they’re the Riley style – love how they fit oversized and that they’re super high-waisted. I got my usual size in them!

6. Midi Skirt & Booties Winter Outfit

winter outfit, business casual winter outfit, red and black midi skirt, black booties, black tights, moto jacket, black turtleneck

Outfit Details: Turtleneck // Red & Black Midi Skirt (wearing size US2) // Leather Moto Jacket // Booties // Sunglasses

I’ve been having to get a little more creative with my outfits here in Denver since it’s so much colder than Dallas! Here I paired my fleece-lined leggings with a midi skirt and booties – I love how it turned out! And I was warm all day!

7. Layering a Dress & Turtleneck Winter Outfit

casual cute winter outfit idea with jumper dress, black turtleneck, black tights, and combat booties

Outfit Details: Turtleneck // Pinafore Dress // Tights // Combat Boots

8. Pull Together All Black For a Chic Winter Outfit

all black winter outfit faux leather leggings oversized black tunic sweater snakeskin headband snakeskin bag

9. All Black with Statement Boots Winter Outfit

all black winter outfit idea with snakeskin tall boots, winter date night outfit idea

Outfit Details: Turtleneck // Faux Fur Jacket // Jeans // Tall Snakeskin Boots

I’ve loved styling all black looks lately! This is one of my favorites to date with the Tall Snakeskin Boots. It was perfect for date night a few weeks ago!

10. All Black with Statement Coat

Outfit Details: Coat // Turtleneck // Jeans // Boots

11. Statement Plaid Coat Winter Outfit

winter outfit idea, black turtleneck, plaid duster coat, black booties, casual Friday work outfit winter

Outfit Details: Turtleneck // Coat // High-waisted Jeans // Booties

12. Casual Winter Outfit With Sneakers

casual winter outfit idea with sneakers, golden goose silver sparkle sneakers

Outfit Details: Sweater (wearing size XS) // Good American Good Legs Jeans // Sneakers (my exact sneakers are sold out – they’re from several years ago)

winter outfit with cropped sweater and highwaisted jeans with scarf and sneakers

I love a good high-waisted jean and cropped sweater combo! With this look I threw on my GO-TO cashmere scarf to keep warm and completed the looks with some fun sneakers for running around town!

13. Skinny Jeans & Booties Winter Outfit

casual cute winter outfit idea, skinny jeans and oversized chunky sweater

Outfit Details: Sweater // Jeans // Split Shaft Booties (33% OFF)

14. All Black on Bottom Winter Outfit: Black OTK Boots & Black Jeans

Outfit Details: Sweater (40% OFF) // Jeans //Stuart Weitzman OTK Boots // Purse

15. Warm Coat & Chunky Scarf With Statement Boots

winter outfit idea grey coat, black jeans, white booties cozy scarf

Outfit Details: Coat (wearing size Petite 0) // Jeans // Booties // Scarf

16. Winter Whites Outfit

rolled up and tucked in winter white jeans
winter white outfit all white look with brown suede boots

I don’t wear a lot of winter white, but when I do I LOVE how it looks! I love mixing winter whites with creams, tans and other shades of brown like tan and cognac.

17. Winter Athleisure Outfit With Puffer Coat

Outfit Details: Jacket // Long Sleeve Workout Top (I wear these ALL the time! I wear size 4) // Wunder Under Leggings (I wear size 4)

18. All Black Outfit with Statement Belt

winter outfit all black with statement belt

You really can do so much with an all black outfit! For this look, I tucked in my fitted shirt to high-waisted jeans and completed the look with a statement python belt. I love how it turned out! I think this look would also look great even with a black belt if it had some gold or silver hardware to break things up.

19. Coordinating Sweater and Booties With Statement Beanie

Coordinate Your Sweater and booties winter outfit statement red beanie white booties grey cashmere scarf

I wore this while in New York during late November and it was perfect for walking around and exploring the town. I loved how the grey cashmere scarf added a little break to my white sweater, white coat and white booties. And then the red hat with pearls was the perfect touch of color to tie the look together!

20. Winter Outfit Pairing Blush and Tan Together

tall suede boots black jeans cropped sweater

I love playing around with different shades of blush and tan – I think they look so great together. I’ve paired the two with grey, black and white before. In this look above, I paired tan and blush with black high-waisted jeans and I love how it looks!

21. Layer a Turtleneck Under a Faux Fur Vest

turtleneck with vest winter outfit

I don’t usually wear vests but I loved this one! I love layering vests over a long sleeve fitted tee or a turtleneck like I did here!

22. Pair Black and Brown Together for a Neutral, Classic Winter Look

black and brown winter outfit

23. All Black Winter Outfit with Statement Booties

I shared a similar outfit above with snakeskin tall boots, but I love this more casual look with the oversized sweater and shorter boots! This would also be cute with sneakers or honestly any kind of printed shoe too! I love doing all black looks and pulling together the outfit with either my shoes, a coat, scarf or accessories!

24. Winter Outfit With OTK Boots and a Blazer

how to style over the knee boots

I don’t really wear over the knee boots very often because I feel like they’re hard to pull off, but I think wearing high-waisted pants really help pull the look together. This crewneck, long-sleeved tee is one of my most worm items when it comes to putting together winter outfits! It’s such an easy base piece for putting together all kinds of outfits!

25. Layering a Cardigan Over a Turtleneck

winter outfit black jeans cream turtleneck cropped cardigan western belt

As I’m sure you might have noticed, I love playing around with layering turtlenecks to create different looks. I love any sort of tighter-fitted turtleneck with a layering piece; I think it creates such a sophisticated look! And recently, I’ve been pairing my turtlenecks with cardigans like in this image above.

The 5 Itmes I Grab The Most

As I was putting this post together, I realized that there are a few items that I wear frequently and wanted to round up a few those for y’all! I love all of these items and have been wearing them on repeat this season!

  1. Good American Good Legs High-Waisted Jeans 
  2. BB Dakota Wubby Jacket
  3. Black crewneck, long-sleeved tee (such a good basic!)
  4. White + Warren Cashmere Travel Scarf
  5. faux leather leggings (I wear size small)