10 Ways to Style "BOYFRIEND" Jeans

I’ve been totally lacking in inspiration for outfits as winter just seems to drag on where I am! But i’ve been preparing for spring hard core because I cant wait to finally not freeze my booty off when I wear jeans outside. I totally think jeans, especially super cool distressed and relaxed fit denim is having a moment right now and it’s so easy to dress up or down. I’ve pulled together some awesome looks to give you either a great one-stop-shop to find some new boyfriend jeans for your wardrobe, as well as some great fashion staples. If you aren’t on the market for any certain item, then this post might be great for you to simply just find a little outfit inspiration.

Disclaimer: This post does not contain any affiliate links and I do not monetarily benefit from you clicking these links! I hope these outfits provide some great outfit and fashion inspo! Maybe even a few things to add to the wishlist ;)

Let’s get started!


  1. L’AGENCE Highline Fray Hem jeans, $265. SHOP NOW (or shop this similar pair by Free People for $78!)

  2. Madewell turtleneck sweater, $88. SHOP NOW

  3. Chloé large ‘Drew’ Nappa Leather bag, $1,980. SHOP NOW

  4. Chloé leather ‘Lauren’ sneakers, $570. SHOP NOW

For a movie date you definitely want something comfy enough to sit down for two hours but cute enough to maybe grab dinner before! I think soft high quality jeans and a loose sweater are great because they provide a comfy stretch for eating a little extra candy of course!!

Find great dupes and similar finds to these luxury items in my SPLURGE VS SAVE POST!


  1. UGG ‘Rhodyn’ Off The Shoulder Sweater ($148) SHOP NOW (Or shop this similar sweater by Gibson for $54 here!)

  2. Citizens of Humanity boyfriend jeans ($248) SHOP NOW

  3. Gucci Princetown Loafter Mule ($695) SHOP NOW

  4. Fluer Du Mal Silk Lace-Trimmed Bralette ($75) SHOW NOW (Here are some similar bralettes if this one is currently sold out: one, two, three)

  5. Nico Giani Shoulder Bag (SORRY, this adorable bag is currently SOLD OUT! But you can shop this SIMILAR BAG: All Saints ‘Captain’ Leather Tote ($378) SHOW NOW)

  6. Madewell Heart Earrings ($38) SHOP NOW

  7. Madewell Layered Coin Necklace ($48) SHOW NOW

  8. Halogen Gold Hoop Earrings ($25) SHOW NOW

Going to the library with bae can be super fun and flirty when you show a little skin with a simple off the shoulder sweater with an adorable bralette. There may not be too much studying going on cause you will look so good in these finds! I absolutely love the loafers, they are perfect with a pair of loose fitting boyfriend jeans. A great way to dress them up! Plus, mule loafers that slip on and off are great to wear to the library if you don’t want to feel restricted from folding your legs into “criss-cross apple sauce” LMAO I know I do!!! (If you don’t know what I mean then google it!)


  1. Fiorucci Crop Top ($80) (This specific style top is currently sold out. Click here to shop a similar one.)

  2. Saint Laurent distressed mom jean ($551) SHOP NOW (Or shop this similar pair from Reformation for $148!)

  3. Gucci Princetown loafer in Red ($695) SHOP NOW I own these in gold, they are such a timeless and fun loafer!

  4. Louis Vuitton ‘Palm Springs’ backpack ($2,400) SHOP NOW (Or shop this similar bag from Barney’s NY for $80!)

  5. Gorjana ‘Chloe’ Mini Layered Necklace ($85) SHOP NOW

Obviously I’m super into the “boyfriend” / “mom” jean look right now and dressing them up with a cool top and great accessories. Sushi dates call for a super cool and trendy outfit. If you are like me then you most likely will be taking pictures of your food with whoever you’re on your date with. If your date posts their food, you want your cool Fiorucci top to be in the background cause helloooo, you are a fashion KWEEN.


  1. MOUSSY VINTAGE ‘Isabel’ High Waisted Boyfriend Jean ($360) SHOP NOW

  2. Mansur Gavriel bi-color large tote ($585) SHOP NOW

  3. Everlane cashmere crew ($100) SHOP NOW (there’s a reason why the NYC Everlane store is always so crowded! Their sweaters are sooo comfy!)

  4. Veronica Beard ‘Daelyn’ Leopard Sneaker ($225) SHOP NOW (Or shop this similar pair from Superga on sale right now for $47.37!)

  5. Le Specs ‘Air Heart’ ($69) SHOP NOW

  6. Faliero Sarti ‘Kia’ Cashmere Scarf ($550) SHOP NOW (Or shop this similar scarf by Rag & Bone for $195)

For a trip to the farmers market you gotta be prepared! That’s why I threw in an adorable leather tote bag that can carry all your fresh produce and maybe some flowers too. Sneakers are your best bet for footwear because you’re going to be walk around and probably standing in line and you gotta be comfy! I’m all about practical but FASHIONABLE footwear.


  1. Citizens of Humanity ‘Emerson’ Slim Boyfriend Jean ($248) SHOP NOW

  2. Alcoolique ‘Shelly’ Maribou Fur Jacket ($650) SHOP NOW

  3. Plein Sud Turtleneck Jumper (SOLD OUT) — I found a similar turtleneck here for $140 from Re/Done!

  4. Madewell ‘Gemma’ Mules ($98) SHOP NOW

  5. Phillip Lim bucket bag (On sale now for $649!!) SHOP NOW 

You will be looking like a classy woman sipping wine and eating small plates in this dope furry coat. I think bomber type cut jackets look fantastic with a fitted turtle neck shirt. Pointed toe mules look so pretty with loose fitting boyfriend jeans. I see a lot of my favorite bloggers pairing these style shoes with boyfriend jeans. Plus sleek yet feminine bucket bag by Phillip Lim pulls the look together to make it fancy enough for a nice night out.


  1. Citizens of Humanity slim boyfriend jeans ($218) SHOP NOW

  2. Rails ‘Collins’ military jacket ($188) SHOP NOW (I JUST THINK THIS IS SO CUTE!!!)

  3. Sam Edelman ‘Hilly' bootie ($159) SHOP NOW

  4. Caslon peplum t-shirt ($39) SHOP NOW

  5. Mansur Gavriel mini backpack ($730) SHOP NOW

These white jeans are so crisp and pretty with a gorgeous suede nude bootie. I think this outfit would be perfect for spring time, or even autumn in New England! The green military jacket is light weight but adds a nice pop of neutral colors with the stripes. Paired with an easy to carry leather mini backpack you can freely move about and carry the essentials. I have been so obsessed with Mansur Gavriel leather goods! Their totes and backpacks are beautiful! This outfit just reminds me of sitting outside with friends or a significant other, enjoying a coffee and avocado toast at brunch!


  1. GRLFRND ‘Devon’ Cuff Boyfriend Jeans ($228) SHOP NOW

  2. All Saints leather jacket ($498) SHOP NOW

  3. Anine Bing lace silk cami ($169) SHOP NOW

  4. Gianvita Rossi ‘Versilia’ ankle strap sandals ($325) SHOP NOW

  5. Dolce & Gabana mini purse (The pictured purse is no longer available but I found a similar one here for $585!)

YES! You better hit the town with your girlfriends in these adorable and easy to move in jeans. Inspired by Zoë Kravtiz look pictured above. I think a silk cami with jeans and a leather jacket draped over your shoulders is so sexy and fun! Throw on your favorite black strappy heels and you will be dancing and singing all night with the girls. I threw in a super fun D&G bag that I think dressed up any outfit where you are wearing a lot of black. Instantly adds a level of FUN!


  1. FRAME ‘Le Boy’ distressed boyfriend jeans ($240) SHOP NOW

  2. Zimmerman ruffle top ($532) SHOP NOW

  3. Sol Sana espadrilles ($116) SHOP NOW

  4. Maria Black tusk gold necklace ($139) SHOP NOW

  5. Eugenia Kim embellished woven beach bag ($142) SHOP NOW

  6. Valentino sunglasses ($261) SHOP NOW

That beach bag is EPIC! Also, if you haven’t been obsessed with Zimmerman tops, dresses and sets…well it wont be long after you look at all their pieces that you will be instantly in love! Their pieces are so gorgeous, feminine and whimsical. I’m just soooo in love with that brand!


  1. Citizens of Humanity ‘Emerson’ Slim Boyfriend Jean ($248) SHOP NOW

  2. Splendid ‘Durango’ drapped cardigan ($110) SHOP NOW

  3. ATM Anthony Thomas Melillo t shirt ($85) SHOP NOWYes, I was a little confused about the price of this t-shirt BUT contrary to what I thought, people rave about this brand. Fans think this is the best t-shirt ever because it’s so soft, you can wash it a million times and the shape and color stays looking NEW! and it feels really well. So I think it might be worth it!

  4. Le Spec ‘Entitlement’ sunglasses ($49) SHOP NOW

  5. Chloé ‘medium Marcie’ shoulder bag ($1,990) SHOP NOW

  6. Alexander McQueen sneaker ($490) SHOP NOW

This is for all my mommy readers out there! This look is inspired by Jennifer Aniston. She always looks so put together when she’s spotted walking around NYC in boyfriend jeans, cool white sneakers and a long cardigan or jacket. I think it’s such a classic look that makes you look comfy but also put together. You are definitely going to be the cool mom in this look.


  1. GRLFRND ‘Devon’ Cuff Boyfriend Jeans ($228) SHOP NOW

  2. Chelsea28 Metallic Sheer Turtleneck (Currently on sale now for $35.40!) SHOP NOW

  3. Rag & Bone booties (Currently sold out — I found similar pair here for $230!)

  4. Calvin Klein bralette (Currently sold out — I found a similar pair here for $32!)

  5. Balenciaga ‘Everyday Camera Bag’ ($995) SHOP NOW

Giving me total matrix vibes with this outfit right now and I love it. I think this would be perfect for exploring a modern art museum and even to snap good pictures in! Modern art museum usually have a lot of nice open white space, which would be perfect to model off a cute outfit.

I hope you guys found some dope pieces and style inspo! Stay tuned for more posts like this and MORE!

xo, Chloe