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The Jeans I Wear Every Day

A Cup of Jo: How to Style Jeans

Jeans. Was there ever a staplier staple? Since their birth as work pants in 1873, jeans have come a very long way. Here, along with my favorite Mott & Bow jeans, are five tips for how to wear and style jeans…

A Cup of Jo: How to Style Jeans

Here, I’m wearing the slim boyfriend jeans and the fitted crew.

Give it a test run.
First things first, before you commit to your jeans, you must try them on. Ask yourself: Can you sit down easily? Could you comfortably eat a burrito? Can you frolic? We love Mott & Bow’s home try-on option, which lets you choose a couple different sizes, try them out, and includes a free return label so you can easily send back whatever you don’t want. It eliminates the need to deal with unflattering dressing room lighting, or a horrid my-calves-are-stuck-and-I-can’t-get-out-of-these-jeans-and-the-salesperson-is-asking-how-I’m-doing situation. (This has happened to me more than once, and it wasn’t pretty.)

A Cup of Jo: How to Style Jeans

Wearing my favorite mom jeans in 100% cotton denim and the cashmere raglan crew.

Venture outside your comfort zone.
For years, I was afraid of high-waisted styles, as I feared they’d make me look like I’d just walked out of an 80s sitcom and not flatter my five-foot frame. One day, I tried a pair on a whim and fell in love. Now, these are my very favorite pair. They hold their shape nicely and look good with absolutely everything. (Although these are a close second.) Why not experiment with a silhouette, wash or material you don’t usually go for? You might be surprised!

A Cup of Jo: How to Style Jeans

Dress them up.
A pointy toe pump instantly elevates everyday denim. It’s almost like adding lipstick — just that one thing immediately makes you look polished. I love pairing heels with a boyfriend jean, for a look that feels more fun than fussy. Pairing heels with jeans in a dark blue or black wash skews more profesh. Bonus: A pointed toe creates an uninterrupted line, visually elongating the leg.

A Cup of Jo: How to Style Jeans

Cuff it.
Showing a peek of ankle is a subtle way to change your whole silhouette. When it comes to cuffs, my rule of thumb is: Roll them twice to wear with flats. When pairing jeans with boots, booties or chunky mules, opt for one big cuff. To demonstrate, please refer to my everyday style icon, Timmy from Lassie. The look is classic, requires zero effort, and works for all sorts of adventures.

A Cup of Jo: How to Style Jeans

Joanna wears the high-rise skinny jeans.

Play with a tuck.
The front tuck — This is where you grab just a small section of shirt and tuck it into the front waistband. It can be centered, or slightly to the side. The result is a casual way to define your waist and bring the look together.
The French tuck — (Any Queer Eye fans in the house?) This tuck takes it one step further. Here, you tuck in the whole front half of your shirt, then subtly billow it out just a bit. (See above.)
The full tuck — This is the all-around tuck you want for cleaner ensembles, or when you need to appear polished. A full tuck works especially well if you want to snazz up your look with a decorative belt.

A Cup of Jo: How to Style Jeans

If you’re in the market for jeans, we highly recommend Mott & Bow. Their jeans are made at premium denim mills, but cost less than designer denim. Plus, they’re super comfortable and don’t fade over time. They also offer multiple inseam lengths and carry sizes 14-20.

What’s your go-to jeans style: skinny, boyfriend, high waisted? We’d love to hear…

(Photos by Christine Han for Cup of Jo. In the top photo, I’m wearing these jeans. This post is sponsored by Mott & Bow, a brand we love for all our basics. Thanks for supporting the brands that help keep Cup of Jo running.)

  1. Liz says...

    I’ve bought jeans from here! They’re great! Particularly their high rise skinny. prefer these over madewell’s anyday.

  2. Danielle says...

    I am glad they have plus sizes! Nothing like a good pair of jeans! With jeans, trousers, and shoes, I have learned that quality is better than quality. With jeans, I have like 2-3 styles. I am short, petite, yet curvy, so I like high waisted and skinny (or a combo if at all possible).

  3. Hi – I read your blog every week and I know sponsored posts are carefully considered by you all. I actually decided to get Mott and Bow jeans a while back after learning about the brand from Cup of Jo. Both times I have ordered from them, I have had TERRIBLE customer service. I voiced my complaint to Mott and Bow and it was the worst online shopping experience I’ve ever had. It seems I am not the only one as there are very similar experiences posted to HighYa (https://www.highya.com/mott-and-bow-reviews). Just thought you should know. Thanks.

  4. Ally says...

    Oh my goodness, I clicked on “Timmy From Lassie,” thinking that it was some kind of cute offbeat style blog and completely burst out laughing when it opened on precisely, Timmy from Lassie.

  5. Liz says...

    I love reading cupofjo, especially your sponsored posts that are recommending your favorite products to us in an organic way.

    One caveat. There is only one style of jeans that is above a size 32 at Matt&Bow. Please do more research for your curvier readers! I was so excited for mom jeans in my size, but was subsequently disappointed as usual.

  6. Andrea says...

    I recently bought the most perfect jeans from Old Navy (I’ve never found jeans I absolutely love so saying this still sounds surreal). They are a little high waisted but don’t feel too constricting for my curvy figure. I was inspired by this post to tuck in my shirt today for the first time really ever. I feel a little self concious, but I’ve already gotten two really wonderful compliments!! Thanks for giving me the guts to try it!

  7. Alice says...

    If my arse looked that good in jeans I’d probably spend my days admiring it in the mirror. Arse goals. I’m a mid rise boyfriend kind of woman, I so want to do high rise but they NEVER work on me. Determined to master the tuck though…

  8. Emily says...

    If it’s not too personal, would love to know what size you wear, Caroline? We appear to have a similar body type/height/frame. I have been on a never ending quest for jeans and LOVE the way these look on you. It’s always hard to know sizing when ordering online. Thanks so much :) :) :)

  9. R says...

    Caroline, what inseam did you choose? I am the exact same height as you (woohoo) and never have any clue how online purchases are going to end up… These look great on you!

    Thanks :)

  10. Meredith says...

    Sizes 14-20, but only in one style. Ugh.

  11. Alycia says...

    I agree! And it means less jobs for people. So many store fronts in my neighborhood are empty because everyone is shopping online. I guess we favor not having to “deal” with dressing room lighting over less traffic/less pollution/more jobs.

  12. Carrie says...

    The photo of the black shirt and converse is perfect. That’s pretty much my exact daily uniform. Definitely going to give these a try. I love to hear that they don’t stretch too, I love my Levi’s but they make my ass looks like I’m packing a massive pee diaper after about 2 hours of wear.

  13. Ann says...

    I have had great luck with madewell and jcrew lately. I’m glad the high waisted is back because I was tired of pulling up my jeans! Sorry, sponsor!

  14. Kate says...

    Love these and love the price point!

  15. Taylor Imhoff says...

    Love my Mott & Bow Jeans! Super comfortable and excellent fit. I’ve recommended them to a number of friends who love them too!

  16. Catherine says...

    Gotta get me some of these!

  17. Geena says...

    I’m a big fan of these jeans! So glad they’re making an appearance here on my favorite blog!

  18. Kelleigh says...

    I LOVE my Mott & Bow jeans!! The best fit and my go-to for day to day jeans! Looking good!

  19. cynthia says...

    Beyond my budget. I wore Gloria Vanderbilt’s for years. I bought them from Costco. Unfortunately, they made changes to the sizing, so I’m looking for a new affordable brand.

    • gracemarie says...

      Have you tried Lee jeans?

    • Cynthia says...

      Thanks! I will try them the next time I need a new pair.

    • Krista says...

      I love Old Navy jeans. There are many sizes and styles and they’re very affordable. I’m from Canada and we don’t have Madewell here. I was so excited when I was in L.A. last year to get a pair of Madewell jeans. For me, with the exchange rate, they were quite expensive, and in the end I prefer all my Old Navy jeans.

  20. Sasha L says...

    The slim boyfriend jeans are so cute! I feel like I’ve been wearing a version of those my whole life, always cuffed.

    I’d love to see reader recommendations for their favorite jeans too, in other price ranges, and great for what type of figure?
    I mostly thrift (which can be kinda hell when looking for jeans), but the last couple pairs of new jeans I’ve loved are good ole men’s Levi 501s off Amazon, about $45 I think, and I wear them loose. And Lola stretch boot cut, they have a waist band that’s like maternity so are incredibly comfy. I think they’re about $80 full price (I found on clearance at an outdoor store). I’m built like a 12 yo boy and can’t do anything constricting around my waist (my very favorite *jeans* are overalls).

  21. Beth says...

    Am I the only person who HATES high rise jeans? They look Terrible on me, make my saddle bags look huge and sit right at the fattest part of my stomach. :(

    • Katie says...

      I agree… I am a size 0 and I think they are so unflattering!

    • Sid says...

      I felt this way forever until I found a pair that fit. Now I’m just worried the high waisted trend will disappear too quickly! I am so sick of fighting low waisted pants to keep my butt covered and having to wear a belt. Try on a ton of different brands before you give up.

    • TJ says...

      I think they are awful. I am unclear how Caroline makes them look cute…some kind of spritely magic.

  22. Helen says...

    What are the dressy pumps? Thanks!

  23. Emily says...

    “Could you comfortably eat a burrito?” 😆 You’re the best, Caroline! An important factor in any ensemble selection.

  24. Mónica says...

    Oh my gosh, those glittery heels! 😍 Where are they from??

  25. Michelle says...

    Multiple inseams! *Gets excited* Oh. Right. Very average offerings. Could you please find a cool denim company for tall girls? I mean like 34 – 38 in inseams. Because legs.

    • Cait says...

      Hudson jeans, Michelle. Their “supermodel” length (their term, not mine, haha.) I’m 6’0 with super long legs and they work for me.

    • Bec says...

      I haven’t double checked but Nudie jeans might…they’re not cheap, I wait for sales but they last forever, I’ve had one pair on high rotation for 4 years! Despite mostly being pictured on men they look great in women too! One of my friends is about 5’9 and they look great on her I’m 5’7 and love mine

  26. Motunrayo Shafau says...

    Didn’t expect to see Joanna… felt like the best surprise!

  27. Susan says...

    So tired of jeans that wear like leggings. And ‘boyfriend’ jeans only fit as pictured that if you’re very thin.

    • Sid says...

      I totally get what you’re saying but, having just finally found a company that makes (affordable) pants that actually FIT me, I can promise that just about any style can look good on any body type if you get a proper fit. It might mean “kissing a lot of frogs” but don’t write anything off before you’ve tried it.

  28. Ali says...

    Are they ethical? I can’t see anything on the website about whether they pay workers a fair price, being in Honduras.

    • Raquel says...

      Yes, can we get some info about their factory please? Lovely to hear that it started as a family business but would love to hear more about their employees in Honduras. Thank you!

  29. I love these jeans and I have them in blue, they make me feel so comfortable and they hardly stretch out

  30. Love new-to-me brands, I’ve never heard of Mott & Bow so thanks for the recommendation!

  31. I LOVE that they go up to a size 20. I’m a short girl (4’10) to be exact but I’m also plus sized so it makes it almost impossible for me to find jeans. I’m not sure if these would be too long (I’ll have to look into it) but I love the fact they are plus size friendly!

  32. Nicole says...

    It bothers me that people sell this “try it at home and return them no hassle” bit with zero pause. Having things regularly delivered and sometimes returned to individual homes by delivery trucks (blue apron and every other small internet business that advertises through blogs included with this jeans company) does not help our climate. At yet us blog reading-left leaning ladies care about the environment?? It’s frustrating to say the least.

  33. Sarah says...

    Hmm, anyone know which inseam you would go with if you were 5′ 5”?

    • diana k. says...

      I am 5’5″ and I get a 30inch inseam in most brands. On me this gives me a slightly generous, full length pant leg. It also gives me the option to cuff it it into an ankle-length. This varies though depending if you have tall legs vs long torso (I have short legs), so your best bet is holding a string from your crotch seam to your ankle and measuring it.

    • Nina says...

      You need to measure. Really depends on if your legs are long or short. Mine are short (and so is my torso) but my sister’s are SUPER LONG with an average torso so…just grab a tape measure and measure from your crotch to the top of your foot down the inside of your thigh. If you don’t have a tape measure, take a string and then put it up against a ruler. Now you’ll always know.

  34. Margaret says...

    So glad youre featuring these jeans. They’re my absolute favorite. Best fit and they never stretch out.

  35. Samantha says...

    I know this isn’t the point of the post, but… your butt looks FANTASTIC in those jeans, Caroline! Strut yo’ stuff :)

  36. Jessica says...

    The high-waist, wide leg thing has taken over my wardrobe. I found this pair at the consignment store from some odd brand called “Yoga Jeans” in a nice clean, dark, not-whiskered color that have single-handedly changed my fall sweater style (cropped and cozy is everything) this fall. They are stretchy, go all the way to my waist (and I have a long torso) and make my ass look great.
    I don’t know if I can ever go back to skinny jeans. Even my vintage Levi’s “mom jeans” are taking a back seat.
    Sadly, Yoga Jeans doesn’t seem to make wide legs right now. But for curvy gals, man, wide leg is a game changer.

    • GG says...

      Yoga Jeans are a little company from Montreal who make THE BEST JEANS. They’re also made in Canada, ethically sourced, etc. There’s no going back once you try them on. I now live in Switzerland and every time I go home to Canada I buy a new pair “just in case”.

    • Emmi says...

      Yes! I never wear skinny jeans unless they are tucked into a tall boot. Ladies, try on a pair of bootcuts or flares. So much more flattering on many bodies :)

    • Amy says...

      Yoga Jeans are a Montréal brand! Their jeans are very comfy :)

    • Eloise says...

      These look great. Anyone know if they are available in the US?

  37. Marissa de Souza says...

    I recently read the Rosemary Wells edition of Lassie (beautifully illustrated) to my kids and completely bawled my eyes out. What a story.

    High waisted skinny ankle jeans are my jam lately.

  38. Lynn says...

    Do they stretch out at all? I hate buying jeans that stretch a whole size or 2 bigger after a couple hours. Ugh.

    • Joanna Goddard says...

      they don’t stretch out, which is great. they’re really consistent. i LOVE the boyfriend pair. i have them in black and wear them all the time.

  39. Amy says...

    Would be interested to hear about the environmental aspects of the company. I’ve just listened to 99% Invisible’s ‘Articles of Interest: Blue Jeans’ episode and environmental impacts of denim manufacturing are massive!

  40. I’m all about high or mid waist!! No low cut jeans for me pleaseandthanks. I like to pull them up a little and make me feel cozy and all together once I’m sitting down.
    Allie

  41. Maggie says...

    I love these jeans too! My go to pair when I need to look put together, but also comfortable!

  42. Abby says...

    omg I LOVE these jeans! They’re my absolute favorite. I’m never taking off my Moore Skinny jeans :)

  43. Colleen S. says...

    I wear jeggings. I’m a weird length, because some jeans a 30-inch inseam is great, while others it’s too long. These jeans don’t seem to come in different inseams in all the styles, just select ones. The skinnies are either 30 or 32, and the mom jeans seem to be the length I need (32 inseams were what I wore in high school, and that is something I’ll never repeat.

  44. Amanda says...

    Would love if they made my size! See @12ishstyle (IG’s) effort to get companies to make a broader size range!

    • Sarah says...

      And sorry, having one style of “curvy” jeans available beyond a size 32 in is not really the same as offering an inclusive range of sizes. You babes look great though!