Styling Boyfriend Jeans for Winter & Friday Five

The Cutest Way to Wear Boyfriend Jeans for Winter
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The Cutest Way to Wear Boyfriend Jeans for Winter

Step outside of your comfort zone and style boyfriend jeans for winter in the cutest way possible.

Who says they’re reserved for the warmer seasons? Boyfriend jeans are one of my favorite kinds of pants to wear. They’re comfortable and different than the skinnies I typically reach for. Usually I find myself pairing them with tighter tops (even bodysuits) or front-tucked t-shirts, but for this outfit, I actually chose an oversized sweater. I wanted to prove that it’s possible to wear two “oversized” pieces together without them looking chunky or shapeless.

Two ways to easily add definition to your body while wearing larger items is with belts and “skinny” shoes. I decided on a patent belt with a larger buckle and sock booties that go higher up on my leg – hiding themselves beneath the hem of my jeans. Just by wearing these two pieces, my outfit looks less bulky and more chic. I even grabbed a larger tote bag which makes my body appear smaller – and the icing on the cake was my baker boy cap. I’m still not over how cute these are, and I’ll probably be wearing them for months (maybe even years) to come.

[ Outfit Details ]

sweater c/o Chicwish | pants | hat c/o Scala via Lipton Publicity | necklace | belt (available in beige and red) | similar booties | earrings | bag

The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter

Friday Five Vol. 2

Clothing Items I’m Eyeing //

This sweatshirt my friend Summer posted about. It’s so cute and so affordable!

It might still be cold outside, but that doesn’t mean I can’t bring more springtime colors into my wardrobe! I’m obsessing over this sweater.

Is it so bad that I just wish for a good pair of black skinnies? This pair is my favorite style.

Articles You Loved //

I may have written this post a year ago, but it’s still getting tons of love. You’ll especially want to read it if you love coffee as much as I do.

Our wedding ceremony was beyond beautiful, and it seems you all loved reading about it as well! Click here to relive it with me.

Not even surprised that ya’ll enjoyed this outfit post as much as I did. Certainly my favorite ensemble from 2019 so far.

Movies I’m Excited About //

Isn’t It Romantic seriously looks adorable. I’m a sucker for a good rom-com.

I’m basically counting down the days until Captain Marvel. If you’ve been reading my blog for long enough, you’ll know I’m a huge superhero buff!

Comedy and action? Yes please. Shazam! seems like a hit waiting to happen, plus it stars one of my favorites: Zachary Levi.

Aaaand of course you might sense a running theme when I say I’m most anticipating Avengers: Endgame. It’ll be an end to an era, but I’m certainly looking forward to it.

New Beauty Products I’m Eyeing //

It’s only a few days until Urban Decay releases their Naked Reloaded eyeshadow palette. I’m a huge fan of the Naked line of products, so I’m beyond thrilled to try this out!

I’ve always loved Origins face masks. Their new release sounds super intriguing.

I keep hearing about this concealer at a drugstore price. Hmmm – time to test it for myself.

Recipes I Want to Try //

I haven’t made anything with seafood yet, and these wraps sounded beyond delicious to me.

It’s been so cold outside that I’m nearly always craving soups and stews. Gimme gimme this goodness.

My husband and I really enjoy spicy things, so naturally this casserole caught my eye!

Related Posts: Casually Stylish Way to Wear a Chunky Red Sweater // Practical Street Style That Is Wintery and Warm

The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter The Cutest Way to Wear Boyfriend Jeans for Winter

Are boyfriend jeans something that you like to wear in the winter?

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The Cutest Way to Wear Boyfriend Jeans for Winter



  • Reply
    February 15, 2019 at 10:22 AM

    This look is SO cute! I love boyfriend jeans and that sweater is everything!

  • Reply
    Anna English
    February 15, 2019 at 10:42 AM

    As a girl with wider hips and bigger thighs, I love boyfriend jeans! They are my go-to denim for sure.

  • Reply
    Katie N
    February 15, 2019 at 10:57 AM

    I love how you paired those booties with your jeans! I always think booties styled like that will look silly on me, but I totally need to try it!

  • Reply
    February 15, 2019 at 11:07 AM

    I love these jeans and sweater together! You look chic and effortless. Your hat style was all over the runways in New York last week for fall 2019-you are ahead of the curve! Love that!


  • Reply
    February 15, 2019 at 11:40 AM

    I SO wish I could pull of boyfriend jeans! They look amazing on you and you styled them perfectly!

  • Reply
    February 15, 2019 at 1:12 PM

    Sock booties and boyfriend jeans do seem like the perfect pair for winter! No cold ankles – my favorite!

  • Reply
    February 15, 2019 at 4:26 PM

    Girl you are ROCKING those bf jeans! They are a trend i just have no been able to make work for me. Going to try again with some of your tips! *wish me luck* lol
    Lee | LegalLee Blonde

  • Reply
    February 15, 2019 at 8:54 PM

    You always look great in whatever you wear! I am a big fan of this look on you.

  • Reply
    February 15, 2019 at 11:05 PM

    I love this look! I wouldn’t think to pair an oversized sweater with boyfriend jeans but you look absolutely adorable! Thanks for the outfit inspiration!

  • Reply
    Indya | The Small Adventurer
    February 16, 2019 at 4:27 AM

    I simultaneously cannot WAIT for Endgame, and I also don’t want it to happen. I know it’s going to heartbreaking, and I know it’ll be the end of so many beloved characters, whether they survive or not, simply because the actors are moving on. I love the Marvel universe so I know this one is going to be a tear-jerker for me!

  • Reply
    February 16, 2019 at 9:38 PM

    You are totally working those BF jeans! Super duper cute!

  • Reply
    Hillary Conheady
    February 17, 2019 at 1:18 PM

    Totally in love with this whole look! And love how you added the hat!

    xo, Hillary |

  • Reply
    Azanique Rawl
    February 17, 2019 at 3:36 PM

    I wish I looked this chic in boyfriend jeans! This outfit is so fun for winter 🙂

    -xo, Azanique |

  • Reply
    Lauryn Hock
    February 17, 2019 at 3:37 PM

    Thank you for the tips! I have the hardest time styling them, but they look amazing on you!

  • Reply
    February 18, 2019 at 9:31 AM

    I love wearing mine all year round too! And I like how how you paired them with the tall booties!

    How 2 Wear It []

  • Reply
    February 18, 2019 at 9:52 AM

    So gorgeous and chic as ALWAYS, Stephanie!! The photo location is perfect for it, too! Love those jeans paired with those boots – the options are endless with them. And yes!! I can’t get enough of that sweatshirt!

  • Reply
    Taylor Mobley
    February 18, 2019 at 9:56 AM

    I love the way that you styled these with those velvet boots. SO CUTE.

  • Reply
    Abbie Gatherum
    February 19, 2019 at 8:28 AM

    Boyfriend jeans are the best! Love this post so much.

  • Reply
    Laura Leigh
    February 19, 2019 at 8:39 AM

    They are SO good!!! And of course, you styled them absolutely perfectly! Really love them paired with those boots gal!

    xo Laura Leigh
    Louella Reese

  • Reply
    February 19, 2019 at 11:59 AM

    SUCH a cute outfit! I really love those boots! Wish I could pull of the jeans lol!

  • Reply
    Laura || Walking in Memphis in High Heels
    February 19, 2019 at 1:32 PM

    I love boyfriend jeans, they’re so comfy! I love how you styled them!

  • Reply
    February 19, 2019 at 1:47 PM

    This is such a cute look! It’s perfect with the hat!

  • Reply
    Jordyn Sifferman
    February 19, 2019 at 3:45 PM

    Okay, I have never really liked how boyfriend jeans look on me but your outfit in this post is SO cute its making me want to give them another shot. Head to toe you look ADORABLE!

  • Reply
    Alyssa Avant
    February 19, 2019 at 6:03 PM

    The sweater is very cute! I don’t think I could pull off those jeans though.

  • Reply
    Kait | Slumber & Scones
    February 19, 2019 at 6:54 PM

    That whole outfit looks so cute and cozy! I love the hat on you so much.

  • Reply
    February 19, 2019 at 11:35 PM

    You look so cute! I love the red door behind you and the brick makes your outfit pop. Cute jeans!

  • Reply
    February 20, 2019 at 12:42 AM

    These boyfriend jeans are so cute and I love how you styled them!! Love it with the oversized sweater too!

    cute & little

  • Reply
    February 20, 2019 at 11:33 AM

    Boyfriend jeans are my favorite right now. So loose and comfy and they look great with sweaters!

  • Reply
    February 20, 2019 at 11:43 AM

    Love how you styled these! and your tote is perfect! x

  • Reply
    February 20, 2019 at 11:55 AM

    I am loving these boots with this outfit! XO


  • Reply
    February 22, 2019 at 6:52 AM

    Love your sweater! You look so cozy.

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