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How to Wear Jeans to Work

jeans-shoes-business-casualHow can you wear jeans to work — and particularly, what shoes should you wear? Which business casual outfits look the most professional? Reader B wonders…

I work in public accounting and we have “Jean Fridays,” but HR says no sneakers, tennis shoes, etc., so I can’t wear my suede Pumas or Onitsuka Tigers with my jeans. Please suggest alternate shoes a girl can wear with jeans to the office. I am a size 8 1/2 and feel like distressed oxfords or driving shoes give me clown feet. And black booties are not the look I’m going for (too motorcycle or bar night or something…). Thanks for any advice if you decide to pick this one up!

Great question, Reader B! We’ve talked about business casual for women, as well as how to wear jeans to work (but back in 2009!).  A lot of this depends on how your jeans are hemmed, but here are a few pointers:

  • A more traditional, structured shoe like a pointed toe pump will almost always elevate a denim look.
  • The wider your pants’ ankles are (bootcut, baby bootcut, etc) the more pointed your shoe needs to be — but shoes with rounder toes can even look better with skinny jeans and the like.
  • You don’t need heels — if you’re more of a flats person, look for either a teeny tiny kitten heel (found with shoes like the Stuart Weitzman Poco) or a pointed-toe flat, like the trendy Nicholas Kirkwood loafers.
  • When in doubt, go for a dark rinse denim with little to no distressing — rips are not appropriate for most offices.

I’ve rounded up a few images from Pinterest to aid you visually, below, and maybe even give you a few business casual outfit ideas…

Below, I agree with this guide to hem length with different styles of jeans (courtesy of Savvy Sassy Moms)… Personally I feel like a rolled cuff is more appropriate for the weekend than for work — even on a casual day — but you should really know your office.  (Ladies, what are your thoughts on rolled cuffs for denim?  Here’s a good guide on rolling denim from Advice from a Twenty Something.)

jeans-shoes-1

Below, I love the look of the monochromatic look with the blazer — very clean and sophisticated, particularly in a greige (courtesy of Outfit Ideas)… the nude pumps help keep the outfit clean.

neutral-jeans-work

Tall boots are still a know your office situation, but I do like the layered look of the blouse, sweater, long necklace, jeans, and boots (picture below courtesy of Bows and Sequins). I always think brown boots are more casual, and black boots are more formal, but that’s just my $.02.

jeans-tall-boots-workThe layered look also works well for work with heels and a blazer — I’d skip the distressed denim for work (photo courtesy of Fashion Inspiration), or with flats (photo courtesy of All Things Katie Marie):

business-casual-jeansI realize I’ve posted a ton of skinny jeans above, so I thought I’d do a quick roundup of a few bootcut jean ideas for work too.  I think these look better with a pointed toe, even if it’s just a slight point, but that’s just my $.02. In the Jennifer Aniston picture (courtesy InStyle), it’s such a simple outfit, but I think would still work in most casual offices — the black pointed boot (that’s taken care of – no scuffs or scrapes), the crisp white blouse, and the gray blazer.  I like the dark rinse, too.  Contrast that with the second picture (courtesy of Torrid), with the lighter distressed denim and the gray, low cut tee — she still looks professional but much less so; just a few changes (darker denim, less sloppy blouse) would make it a bit more polished.  The third, fourth, and fifth pictures are great examples of how a cardigan and a slight point to a shoe can really elevate an outfit. (The Small Things Blog / Taylor Rae Brommel / What She Wore 365).

bootcut-jeans-for-work

Ladies, which shoes do you wear with jeans to work — and what are your favorite business casual looks? Do you agree or disagree with some of these rules for wearing jeans to work?

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Comments

  1. Wildkitten :

    I wear a dark denim with no distressing and pair it with a blazer. Heels or flats both work just make sure your jeans are the right length for the shoe.

  2. I would seriously take a small pay cut in exchange for being able to wear jeans to work. It’s sadly never an option at my office, but jeans are acceptable for some offsite retreats. In those cases, I stick to most of the advice above–nothing ripped, distressed, or embellished. I wear them with an office appropriate sweater or blouse, or with a good quality tee and a blazer. Shoes depend on the location. For a beach-adjacent retreat, I went with flat, beige leather sandals; for an event at a hotel on a very snowy day, I tucked the jeans into flat brown leather knee high boots.

    • I am so with you. I promise I would only wear dark rinse non-distressed jeans. I would keep the rest of the outfit super classy. JUST LET ME WEAR DENIM.

  3. Pet peeve :

    Sorry. I know jeans are casual and you may wear them to your place of business, but they are not “business casual.”

  4. Anonymous :

    I live in CA so the weather is nice year round. I wear ballet flats a lot, mostly round toe ones. I wear them with both skinny and bootcut jeans. I agree they look better with the skinny jeans, but I don’t really care. Sometimes I’ll wear skinny jeans + knee high boots in the winter, or jeans and booties (cuffed jeans are fine in my office). I don’t do heels and jeans. I like the look, particularly skinny jeans and pointy toe pumps, but personally, if I’m allowed to wear jeans I really don’t want to bother with heels.

    • SoCalAtty :

      Second all of this! I’m in house in a creative industry, and I don’t do jeans every day, but probably twice a week. Those are pretty much the rules I follow. I want to be comfortable, and for me that is flats.

    • I agree on jeans + heels. What’s the point of wearing jeans to work if you have to wear heels anyway? My favorite shoes to wear with jeans to the office are penny loafers, flat boots, or boat shoes. (Not sure if the latter is too casual for OP’s office).

    • Yeah, all of these looks would be everyday office wear everywhere I’ve worked in the past 20 years in California. Admin to CEO. All week long, not just Friday.

      That said, I think the Jennifer Aniston pic is the most ‘professional’ of them all. It’s simple & nicely rides the line between dressy & casual, thus perfect for business casual Friday.

  5. I wear straight leg or trouser cut jeans, no skinnies, on Fridays. I pair it with a blazer or nice blouse and pumps.

  6. MBA in training :

    I did jeans a lot at my last job (in a dressed-up way, for a more trendy office), and do jeans even now for almost all but official “business formal” corporate visits. Always stick with dark wash, very good condition, well-hemmed (seriously, costs like $10 and makes things look so much better). No cuffs… I think it looks like I haven’t had time to go to the tailor.

    Shoes- usually flats with a somewhat (not totally) pointed toe. Sometimes I’ll break out a 2 in. heel, if it’s a nice day. I’m with Kat that a more pointed toe is best because many round-toe flats tend to look frumpy. Tall boots if the weather is crappy (like this entire month)

    My fallback outfit is finished off with a blazer and nice necklace, to keep things structured and polished.

  7. If the letter writer finds black booties too motorcycle/bar night, what about Chelsea boots?
    Or, if the LW likes the look of sneakers with her jeans, what about some cute oxfords? I can say from personal experience that non-bulky ones like this make one’s feet appear quite dainty…. http://www.6pm.com/miz-mooz-miley-bronze

    • These black suede ones are cute too: http://www.6pm.com/nine-west-zeau-black-suede

      • And these are a bit more dressy: http://www.6pm.com/penny-loves-kenny-north-black-metallic-tumble-matte

    • N.C. anon :

      Love the first and third ones, although the picture makes me wonder how well made the Miz Mooz ones are (the soles don’t look well attached to the rest of the shoe). Great prices too!

  8. TJ alert: I am wondering what you guys think about my issue….

    I am 1 of 5 friends (all females, some married, some single, some with job and some without) who have known each other for a very long time (20+ years). However, I’m always the one organizing events and get-togethers since it doesn’t get done if I don’t do it. No one literally does anything unless I instigate and plan. However, I’ve gotten tired of doing this lately. Its not like I don’t have time, I do but it just gets to the point when enough is enough. It doesn’t take a lot of time (email, texting, etc) so I don’t see why this is a task no one else will do. Maybe it is because I always do it so they think it will get done. Question: Is it wrong of me to just take a step back and see what happens when I don’t step in? We are having another get-together and I’ve already planned and designated tasks. Some people are dragging their feet or plain think its not important enough to remember. The event will fail because I am refusing to remind people about their tasks. They know what to do but I need to remind them and by not reminding them, they won’t do it and it will fail. What should I do?

    • Diana Barry :

      What do you mean, fail? Like someone is supposed to bring X kind of food and they won’t remember?

      Short answer, it is fine for you to step back. It may be that these get-togethers are most important to you so you are the one who gets stuck with the planning, and without your planning they just won’t happen. OR it may be that other people will step in and plan for the next event.

    • Anonapotamus :

      You are so Monica Geller.

    • I’m with Diana Barry – what are these events and what are the tasks? If it is something like a trip to Las Vegas and everyone lives in different cities, I can see why that takes a lot of planning. But if it’s just getting together for dinner on the weekend, I’m not sure why all the tasks are important. To be honest, if one of my friends was assigning everyone tasks for a simple get-together, I would probably ignore it until an hour before the get-together when I looked up what I was supposed to bring and grab that on my way over. People are busy and planning an elaborate event just might not be a big priority for your friends.

      • If I was assigned a “task” for a get together other than “bring wine” or “bring app to share” I would absolutely not do the task… you need to be more specific. That, and I bet your buds don’t like you telling them what to do (you may think you’re being organized; they may think you’re controlling), so take a step back and see what happens.

    • anonymama :

      Maybe get through this last “event”, and after that take a step back? It is understandable that you’d be tired of doing all the work, but it would be kind of… abrupt? (passive aggressive?) for you to all of a sudden just stop doing everything, without any warning to anyone else or any hints that you are tired of doing all the organizing. And it would be weird if it was kind of your event that you’re getting together and you just stop doing anything for it. I’d say either do your normal thing through this last event and then stop, maybe letting them know that you’ll let someone else step up to organize the next get together, or if you really can’t stand to do it anymore let them know (not in a drama way, just in a “I’m sure you’re as tired of me getting on your cases as I am of getting on your cases, I’m not going to send any more reminders and hope to see you at the shindig.” or even “sorry I realized I can’t make it this time, I’ll let someone else take over the group planning.”)

    • S in Chicago :

      For what it’s worth AnonCA, I think folks are being a little too rough on you. I’m the hub/planner of a similarly sized group of folks from college times and we’re all now early 40s. I totally get where you are coming from and not even in regard to something as important as a baby shower. Our group gets together only once or twice a year and even simple things–find a date that works for everyone, find a location that works for everyone (city vs. suburb), etc. gets annoying when you’re trying to work around all those folks’ schedules (and later their kids’ schedules). Even if it’s just well-meaning emails and texts as everyone tries to find times that work for the others, it gets annoying. But to give you the other side of the coin, I stepped back three years ago and now we haven’t gotten together as a group (in full) for three years. Some have made it to a birthday or dinner for one or other at times but it’s not the same. I skipped one of those dinners and was so disappointed I missed seeing seldom-seen friend. I know my group of friends values each other. Heck, we’re still friends 20 years later. But Facebook updates aren’t the same. I know I could send out a group email and get us together again–but my feelings are really kind of hurt that it takes me doing this and it just feels like a whole lot of work on top of a life that’s really busy right now. (What’s weird is that some of them will even suggest to me that I should try to get everyone together….sigh.) I guess people get used to roles. I think it comes down to balancing how much you want to see them vs. the effort to do so and you just have to accept it. It’s easy to have a bar meetup when you’re late 20s. Much harder when kiddos and hubbies and suburb migration and work travel, etc. begin working their way into not only your life but everyone else’s.

      • Just get your friends together again. Not everyone has that gift. Life is short.

  9. Sorry, this is meant as a reply to AnonCA’s comment above

    I’m having a hard time imaging what activities you guys all do that are so complex that require lots of emails to plan and assign tasks.

    Maybe just chill out a bit?

    It seems like you like to plan every detail of an event but others prefer to be more casual about get togethers. Try it their way for a bit and see what happens.

    • I agree with this. How hard is “Show up at X wine bar. Drink wine.”

    • Gilda and Diana…Thank you for your suggestions. You might be right in that it is important to me and not as much to them and perhaps I should chill out a bit. We are planning a baby shower for another friend so the dilemma is do I chill out a bit to let people do things on their own which means it doesn’t get done or do I step in a bit more so that the baby shower for this friend of ours is a nice shower?!?!? That is my issue. I vote on stepping back but my SO thinks that the end product is the pregnant friend who deserves a nice party despite all of this.

      I guess my overall issue is that I feel like I try hard to make things nice for us (which doesn’t take much effort from me) but I don’t feel it is returned. For example, I plan everyone’s birthday parties but no one plans mine. I plan someone’s going away party but they never care to plan anything for me. I host bridal showers but never got one myself. I always volunteer to do the most work, make the most food and pay for the most of anything and I’m the one with two small kids, a full time corporate job with lots of responsibilities who lives 50 miles away from everyone else. I’m not the single person or the stay-at-home mom in our group. Plus what is worst is that this baby shower was never my idea. I’m too busy but I was asked to do it by another person.

      • Not being snarky, but how old are you? Who is still planning birthday parties that require more effort than “Hey, let’s all grab dinner on Saturday at 7 pm”?

        It sounds like you have a lot more invested in these friendships and on having successful activities than the rest of your friends do. Time to step back.

      • Are you hosting the baby shower?

        If so, then yes, delegate. But i don’t think her shower will be ruined if someone forgets the salad. I really think that you chill out and remember what the point of the event is. It’s for you all to wish your friend well before she has her baby and possibly to help her out by giving her some baby supplies. Those are the only things that has to happen in order for this event to be a success. It doesn’t need to be pinterest worthy or filled with gourmet foods and decorative crafts.

        If you are not hosting, I think you need to do the piece of this that you were asked to do by the host and then just show up with a lot of love and good wishes for your friend.

        It seems like you’re making this way more stressful than it needs to be.

      • Gotcha. Replied before I saw your follow-up. Given that it’s a baby shower, I can see why it requires more effort. That said, if you are also busy and frustrated (which it sounds like you are), I’d see how many tasks you can drop while still having a nice shower for your friend. Food, cake, favors, decorations — all that stuff can be ordered rather than made.

        As for birthday parties and going-away parties, I’d just stop doing them. It sounds like your friendship group (like mine!) is no longer all that interested in birthday parties and going away parties, so save yourself the trouble and let them go.

        • I agree with Gilda re: baby shower. It’s also ok to say “no”. As for the rest: show up to bar. Drink. Say happy birthday/ goodbye. What more is there? You need to chill way out.

      • Anonymous :

        I would seriously dread going to any of those elaborately planned events. No fun at all.

      • anonymama :

        I think you need to reassess what you volunteer for, and what a “nice party” means. I mean, it sounds like either they are oblivious about how uneven the workload is, they think you just enjoy doing all the organizing, or they might actually resent that you take over everything and maybe have different priorities than everyone else in what your get togethers should be like (I suspect it might be this last one based on them dragging their feet, and you already having a to do list and tasks assigned before consulting with anyone). You mean well, and to you doing this work is clearly part of being a good friend, but I think you need to take a step back, as it doesn’t appear to mean the same thing to them. It’s okay to say no to stuff even if someone asks you to do it.

  10. You dispute the propriety of tall boots at the office, but have no issue with the way the woman in that photo has her shirt hanging out of every opening of her sweater. I’m having a hard time with the contrast. To me the untucked and possibly oversized blouse is much more sloppy and casual than her boots. I’d say both issues are definitely Know Your Office.

    • anonymama :

      If it’s the tall boots picture you are referring to, it seems like the problem would be more that the shirttails are actually not even long enough to stay tucked neatly. If it’s fitted, I don’ think an untucked shirt would necessarily be out of place in any situation where you’d wear jeans. Also, typically the collar and cuffs of a shirt do “hang out” of a sweater, so the “shirt hanging out of every opening of her sweater” made me laugh. It does look like a chambray shirt with jeans though which to me would be pushing it more than an untucked shirt.

  11. I wear jeans most days and stick to dark denim + flat/wedge + tank/shirt + cardigan. If I feel up to it, I’ll substitute the shoes with a heeled boot or tall boot (with skinny jeans). That said, I’m in a creative field where you can wear jeans to practically anything.

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