How to style boyfriend jeans for a refined casual look

Susan B wearing ivory sweater, gold necklaces, boyfriend jeans and loafers.

I’ll admit, lately it’s been challenging coming up will new outfits without coming completely untethered from reality. 😆 And I do try to keep it real.

earrings (similar) | charm necklace | lariat necklace | sweater (Plus) | ring | jeans | shoes (similar)

Though we’re not on full lockdown, Los Angeles is still a Covid “hot spot.” So we’ve mostly been sticking close to home. Jeans And A Sweater has been my default setting. I thought I’d take that formula and tweak it just a bit.

Sweater, boyfriend jeans and loafers

This cashmere crewneck is from Lands’ End (and currently marked down with code CLEAR). It’s a little more opaque than the similar style from J.Crew, but still light enough to layer under a jacket. And it’s offered in Misses, Petite, and Tall and Plus sizes.

While sneakers are a no-brainer these days, loafers are a comfortable alternative that takes the look up a notch or two. I’ve always loved the look of straight leg or boyfriend jeans worn with loafers. There’s a fun balance between relaxed and classic, rough and refined that appeals to me.

Susan B sits wearing ivory sweater, cuffed boyfriend jeans and loafers.

Seated mirror selfies seem to be a “thing” these days, so I had to give it a try. 😉 (It’s been too windy the last few days to take photos outside.) I purchased these Dorateymur loafers a little over a year ago, deeply discounted but on final sale. (Here’s the same style in white.) They ran about ½ size large, but I loved them and decided to keep them anyway. I recently tried adding cushioned insoles, and hooray, perfect fit!

Here’s another similar loafer style: Frame

Susan B wears a cashmere sweater, distressed boyfriend jeans, yellow square-toe loafers.

While I love these raw hem boyfriend jeans, and wear them regularly, I’ve been somewhat hesitant to include them in the outfits I post. That reflexive voice in my head that says, “but they’re not flaaaattering” makes me second-guess myself.

Do they make my legs look shorter and maybe thicker? Possibly. But you know what? I’m choosing not to care. I LOVE the overall look of this outfit.

Here’s how I styled them for warmer weather last year.

Tools, not rules

I’ve been trying to practice what I preach about not letting (sometimes arbitrary) ideas about what’s flattering dictate my personal style. Sometimes we’re our own worst critics. And sometimes our notions of what’s flattering can become outdated.

I’m a great believer in “tools, not rules.” Style guidelines are just that: guidelines. Sometimes it’s the exception to the rule that makes an outfit sing. And I think feeling authentic and joyful in what we’re wearing creates confidence, which is probably the most flattering thing of all.

Do you have a favorite “unflattering” piece that you wear anyway?

Stay in touch.

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34 Comments

  1. Robyn
    February 22, 2021 / 2:33 am

    You look great in the boyfriend jeans. Adding the loafers ups the level of the outfit. I too have been experimenting with jean styles, shoes etc. here recently I’ve been wearing work trousers at home. They’re more comfortable. One thing I do know; I’m am so over lounge wear. Lounge wear was something I looked forward to wearing after a long day or on Sunday, but not now. How about an idea for a post? I’m always looking for the elusive cotton sweater. Preferably no dropped shoulders or boxy. I’m willing to pay a finders fee?

    • Susan Blakey
      Author
      February 22, 2021 / 5:50 am

      Thanks, and yes, I’m on the hunt for cotton sweaters! 😉

  2. Lise
    February 22, 2021 / 3:30 am

    You look fabulous in these jeans, just shows our own ideas are not always an accurate reflection. My unflattering piece that I wear anyway is a Teddy Bear Jacket in cognac. When it is zipped up I really look like a teddy bear (in the middle section), but I don’t care, I love it and feel snuggly in it. 🙂

  3. February 22, 2021 / 4:25 am

    Thank you for schooling us today on how to keep a more youthful look in our everyday styling choices. I feel that the combination of a more vintage piece mixed with a more classic item creates that style that keeps us more current but not trendy. I love the neutral sweater that you can accessorize with whatever color or vibe you are feeling that day. I just added a pair of slim boyfriend jeans to my wardrobe and look forward to mixing it with linen and other more refined pieces. And, love those shoes!

  4. Kris
    February 22, 2021 / 4:47 am

    Love this outfit Susan! Your boyfriend jeans look great on you. I think it’s a bit that we need to adjust what we consider flattering…? I don’t find anything about this outfit unflattering. Your loafers are gorgeous and show off your slim ankles/feet that peak out from your jean cuffs.
    I have the J Crew version of your sweater on order. Same colour as I am a spring as well and ivory is one of my best colours. I intend to style it with my boyfriend jeans too.

  5. Christina
    February 22, 2021 / 4:57 am

    Hmmm – either your exercise program is really working or those jeans are totally flattering or both! Really like this look – colors and gamine style are in your wheel house while achieving a “classic” tailored look .

    • McKlem
      February 22, 2021 / 6:59 am

      I agree about the exercise program. Top and bottom, I think you look trimmer. And very put together.

  6. Ms. Liz
    February 22, 2021 / 5:22 am

    You look smashing! I totally understand what you are saying. I second guess myself all the time – even after I have purchased an item I initially loved. I have all these “rules” (is it the right colour for me, should I have sized up or down, is the neckline too low etc. etc.) in my head and my perfectionist tendencies start to come out. Thanks for posting this – I need to just enjoy!)

    Also, I really enjoy your posts on how you style your wardrobe items. I love the mix of refined and casual. Those shoes are the bomb!

  7. Becky
    February 22, 2021 / 5:55 am

    The “ Tools , not rules “ paragraph is fashion wisdom !
    Well said and quite profound really.
    Thank you, Susan.

  8. Diana P
    February 22, 2021 / 6:04 am

    I love this look on you, so youthful, relaxes, and comfy looking while polished! It’s my favorite look. Good loafers are some of my favorite shoes. I live Mephisto and Paul Green for a comfortable, stylish loafer.

  9. February 22, 2021 / 6:41 am

    Thank you for posting this outfit, the boyfriend jeans are terrific and shows we can wear any trend if styled for our age. The necklaces bring it up a notch too. I am always unsure of the shoe to wear for my stay at home life style. I tend to go casual since my day is spent on my feet. I always appreciate your shoe suggestions for comfort. Thanks for the inspiration.

  10. KWM
    February 22, 2021 / 7:27 am

    THey look just fine on you! Had you not questioned that, I would never have even given it a thought.

  11. Wendelah
    February 22, 2021 / 7:39 am

    You always look fantastic to me. It wouldn’t ever occur to me that your legs look shorter–or whatever–in anything you wear.

    Frankly, I consider changing out of my pajamas a victory these days. Apart from walks around the neighborhood, and many visits to my husband’s many physicians, I’ve barely left the house in months. I wear running shoes (Brooks) or sandals (Finn Comfort) outside. The only shoes I’ve worn inside for nearly a year are a pair of sturdy woolen clogs by Finn Comfort. They’re comfortable and supportive–and they keep my feet warm in winter and cool in summer! They’ve gotten so much wear that I had to replace the insoles.

  12. MWG
    February 22, 2021 / 7:47 am

    Great look! You look terrific.

  13. February 22, 2021 / 7:57 am

    Well, yes, I wear “unflattering” things all the time, if we define flattering as “that which emphasizes all the ways in which my body might still comport with the lines of the male-desired archetype;). But if we define “flattering” as being “that which emphasizes an aspect of myself that I want to communicate because it makes me feel good in my being to do so,” then, no. LOL.

    Also, my first thought on seeing you in those jeans was that the workouts/eating you’ve been doing have made you leaner and more muscular, which I find very flattering in the traditional sense! So! Flattering in that sense is also somewhat subjective! tl;dr where what feels good! As you know, and as you already do;).

    • Lisa
      February 22, 2021 / 7:59 am

      Also I love those shoes and find them very Une Femme:).

  14. Jennifer
    February 22, 2021 / 8:01 am

    I’m with poster Robyn–I am totally over lounge wear! Two weeks ago I bought a cute pair of satin wide leg lounging pants and almost kept them but thought to myself “when we re-emerge and start going out again the LAST thing I am going to reach for is these pants!” So back they went. I was never a huge fan of lounge wear to begin with (makes me look and feel frumpy, generally) and I miss wearing pretty dresses, (low) heels, and carrying my handbags (which have been sidelined for smaller, hands free options.) But I do think more casual clothing will be the new norm, so I love your ideas on how to create those looks. I love your boyfriend jeans and think they look great on you! Looking for clothes that flatter but don’t try too hard is an ongoing battle after a certain age, I think. As my body shifts, so do my beliefs about what is appropriate and flattering on me. Thanks for giving us more to think about on this topic!

  15. Lily
    February 22, 2021 / 9:17 am

    You look like a million bucks here! Wouldn’t change a thing. Do you think your LE cashmere will last more than a season? Is it warm?

    As far as wearing less than flattering pieces I would say I wear the “wrong” colors all the time. Firstly, I love black. If a garment makes me smile, that smile is going to make up for any “bad” colors!

    • Susan Blakey
      Author
      February 22, 2021 / 10:30 am

      Hi Lily, thanks! The sweater is warm enough for our climate (though if you live where winters are frigid, you’d probably want another layer). It’s too early for me to tell how long it will last, though it does seem to be a tighter weave.

  16. Lisa G.
    February 22, 2021 / 9:47 am

    Thanks for your honest words of advice and showing daily looks. New isn’t always necessary. We are all looking for new ways to style our existing clothes. I think you look great in these jeans!

  17. E
    February 22, 2021 / 9:53 am

    Love the outfit. I also appreciate how your ring mirrors the circles on the loafers — intentional, I am sure!

  18. February 22, 2021 / 10:06 am

    “Do they make my legs look shorter and maybe thicker? ” Are you serious? You’re way to hard on yourself. You look fab. Give yourself a break. You don’t need to overthink this stuff for it to be appealing. Looking good lady!

    • Anon
      February 23, 2021 / 8:46 am

      I thought frayed-hem jeans were silly, until I tried them. They work so well in the right cut, color and length. People comment on them, but I just engage them in a conversation about how you never know until you try it. Is it a fad? Maybe, but what is wrong with having one fad item that you really like and wear to pieces? The fraying gets better with time.

  19. Renee
    February 22, 2021 / 10:24 am

    You look fantastic in this outfit! Yesterday, I ordered a pair of boyfriend jeans. So, looking forward to wearing something other than my workout pants (probably unflattering, yet comfortable) and skinny jeans. Thanks for the styling idea!

  20. Elizabeth
    February 22, 2021 / 10:36 am

    Great look! I love the loafers. Are you wearing socks? Do you have ones that stay up? I have small ones but they always fall down. And my feet get sweaty with no socks( Sorry, TMI) ..what is the secret?

    • Susan Blakey
      Author
      February 22, 2021 / 11:03 am

      Hi Elizabeth, thanks! No I’m not wearing socks. The padded inserts keep my feet comfortable. But I’d also wear these with my favorite no-show socks instead of the inserts.

  21. Joan Nackerud
    February 22, 2021 / 11:56 am

    Hi Susan,
    I love the idea of boyfriend jeans but find the proportions hard to work with (5’3″ and curvy). Usually I really like AG jeans. I don’t think the shape is the issue for you, but this specific jean — to my eye too much random whiskering and fading. I do like the casualness of boyfriend jeans with blouses and tops. I think AGs older versions looked better. Really enjoy and learn from your finds and combos. Thanks.

  22. Lee Rosenthall
    February 22, 2021 / 2:00 pm

    I’m in love with those loafers! And the jeans look great on you. (Everything looks good on you these days.) Need to go check out those cashmere sweaters …

  23. Ainsivalavie
    February 22, 2021 / 2:35 pm

    Sitting here in my LLBean fleece housecoat, wearing my Ryka walking shoes ( only because the Amazon delivery arrived a few minutes ago or would be wearing my lime green Crocs) hair in messy bun mode, wearing glasses because too lazeee to put in my contacts…watching the gazillion snowflakes litter the yard. I am the last person to comment on fashion/lounge wear/ style. I am retired and under lock down…lounging is my life after 36 years of professionalism. Anyway I like your comments about tools not rules. I don’t intentionally buy colours that may not be for me but I did spring for a pale lavender cashmere sweater ( it’s called opal) more blue than pink. It’s very pretty but not enough pizazz for me so I jazzed it up with a Kelly green, lavender & black Dior silk scarf near my face and it looks awesome! The opal now actually works for me tho probably not my season or whatever.
    For what it’s worth ( and I own over 20 cashmere sweaters, have a bit of an addiction ) Land’s End are a darn sight better quality than JCrew. Even in my climate under a parka they are heavy enough and no pilling. JCrew are ok if you get a really good sale but I find they are very light and pill a lot. Honestly the only non pilling cashmere item I have is a 700.00 ruana I bought for 75.00 on Poshmark. ( really!!)
    I really like the jeans but I need an edgier look with the foot wear so kitten heel pointy toed ankle boots, Converse high tops, thick soled J Slides or Docs. Leather moto jacket over the cashmere.

  24. Judy B
    February 22, 2021 / 5:20 pm

    Susan,
    I really like the refined casual outfit you’re wearing—a good model of the style. And I have to agree with your final remarks—tools, not rules, and especially the idea that feeling authentic in what we’re wearing inspires the confidence, which is what’s really flattering. More excellent ideas to think about!

  25. Janet D.
    February 22, 2021 / 8:07 pm

    I flatly stopped second-guessing myself years ago & now go exclusively by the first impression I get when I look in the mirror. If what I see pleases me, I keep it. I don’t stand there picking it apart or asking “yeah, but….” or wondering if it’s too bright, too bland, too short, too long, too this, too that. That kind of nonsense just makes you uncertain & insecure & you’ll never be confident in whatever it is you’re wearing. And I’m convinced it’s not the way the clothes LOOK on us as much as the attitude they imbue us with WHEN we wear them. If I feel good in an outfit, I strut. I feel confident, empowered, together, attractive, full of beans. That’s how I want to feel. The only other thing I think about is how it fits: does it pull anywhere? Gape? Constrict my movements? Does it hang properly, do the seams match if it’s a print, is it well-constructed (fussy ex-sewer here). Does it need constant adjusting? And then of course we all have our personal likes & dislikes. I love red, hate burgundy. Love strappy sandals & leather boots, hate big clunky shoes. Avoid wrap tops because they always gape or pull on me. Avoid anything “prim”. Love leather motorcycle jackets with lots of flaps & pockets & zippers & studs. Once I put all that together — do I like the look, does it reflect who I am, do I feel great in it, is it comfortable, does it do what I want it to do — I stop asking questions because I learned long ago that we can talk ourselves into doubting ANYTHING if we try hard enough!

  26. February 23, 2021 / 10:46 am

    Love “tools not rules!” We are all of an age when rules are not our top priority in dressing. The outfit looks fab on you. The fact that you question whether the boyfriend jeans make you look fat only shows that you are human. Most of us ask ourselves the same question. The unflattering thing I do: wear warm browns (cinnamon, nutmeg, copper) in the fall. However, I’m not changing that! Thank you, Susan!

  27. Pink Azalea
    February 26, 2021 / 8:08 am

    I love the jeans and loafers and don’t think the jeans are unflattering. They look fine to my eye. I would love to have the shoes, but in white my feet would look like boats. To me, understanding what colors, cuts, and styles are most flattering feels freeing rather than limiting. Within the “best for me” I find a lot of room for creativity. When I buy something that doesn’t match up with what I think looks best on me, those are the items that tend to get donated. Susan, you mentioned wearing sweaters and jeans often. I am working on creating a weekday “uniform” for myself. That might be a good topic for a post.

  28. February 26, 2021 / 8:33 am

    No, these jeans are perfect for you. They do not make your legs look shorter or thicker. If they were, I would tell you (in a DM haha).
    The shoes are to die for. I would love a pair like these. Provided I can wear them with bare feet which is usually not the case with closed shoes in summer.
    Greetje

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