How to Step Up Your Working Wardrobe

How to Step Up Your Working Wardrobe

2017 Update: We still stand by this advice on how to step up your working wardrobe (and links have been updated below!), but you may also want to check out our more recent discussion from our Next Step series on the different tiers of professional clothing brands.

How do you step up your working wardrobe when you want to be considered for a promotion or raise? Reader U wonders for her business casual office…

I work at a company where there are no strict guidelines to what we should wear. Most days, we are fine wearing casual to business casual. Even with my position as a forecasting specialist, i am not requested to wear something more formal. Jeans with a formal top or a dress are my go-to when we are requested to wear something more presentable. However, I am applying for a supervisory position and have start wearing more formal clothes, specially because I need to be at my best. What is the most appropriate clothing that I could look presentable enough but won’t look like I’m trying hard to impress people? Slacks don’t really fit me well – tiny gal with longer torso. Thanks!

We’ve talked about how to look professional in a laid-back office, how to transition your wardrobe from a very conservative workplace to a more casual office,  as well as how to look professional without being overdressed, but we haven’t talked, directly, about how to step up your wardrobe when you want to be seen as more managerial.  I’m particularly interested to hear what the readers say here.  For my own $.02, this is how I would approach it:

– Buy a black or gray suit.  Yep, I went there. I say this not because you need to wear a suit, but because the pieces that I’m going to recommend you start to add to your wardrobe are all pieces of a suit — nicer pencil skirts, nicer sheath dresses, nicer blazers — and your first few purchases may as well just be suiting separates that all match each other (particularly because it’s a waste of time to try to make a suit out of different fabrics).  There are a number of inexpensive suiting options out there for women; in this case I would recommend buying matching suit separates such as a sheath dress, pencil skirt, and a matching blazer.  Check out the EDV line at Macy’s — I’m a fan of the AK Anne Klein suiting separates, but there are also suiting separates from Calvin Klein and others.  If you are really uncomfortable with the concept of a suit, let’s compromise and say you buy a ponte knit suit (like the one pictured in pink above).   Now that you have a suit, you’re all ready for the interview you’ll be getting soon — but more importantly you have some building blocks to work with, like a blazer, a pencil skirt, and a sheath dress.  Even wearing the pieces as separates will step up your game.

– Ditch the jeans.  I like jeans as much as the next person, and maybe there are occasions where your jeans are the only appropriate thing to wear.  But if you can’t wear a dress or skirt (or trousers) instead, at least wear your black or gray blazer with jeans.  (Again, a ponte knit blazer or a sweater blazer is a great way to make a transition.)

– If you feel weird ditching jeans entirely, wear structured denim pieces instead.  If you feel too “dressy” not wearing jeans, try adding a chambray or denim fitted top with trousers.  Alternately, I’ve had fitted denim jackets that I’ve worn to death on top of sheath dresses, how to step up your working wardrobe in a business casual office: wear a denim blazersuch as these budget blazers.

– Sleekify your look.  That may sound odd, but I think overall, “sleek” is a good goal in a lot of places, such as shoes, hair, makeup, and accessories.  Opt for the skinnier heels in your wardrobe, the simpler earrings, the controlled hairstyle.  I’m not saying you have to wear 4.5″ Louboutin heels and get a weekly blowout, but I am saying that if you normally wear comfortable/frumpy/funky shoes and have slightly out-of-control hair, go for a skinny kitten heel or a sleek flat and try to pull your hair back into a neat ponytail, bun, or other easy office updo.

– Wear a watch.  There are a million little things you can do to seem more professional, but I think adding a watch (even an inexpensive one) is a great outward way of showing you’re responsible.  As a bonus, it avoids that awkward moment where you need to fumble in your purse for your cell phone if someone asks the time.

 Readers, how do you step up your working wardrobe when you’re hoping for a promotion or raise — particularly in a business casual office?


  1. Sydney Bristow :

    A friend of mine works in a construction environment and wears jeans a lot. She adds a jacket to dress it up when she needs to look more formal, which I think works well for her.

    I recommended this a few days ago, but pencil skirts are my to to item. If you want to transition slowly to dressing up a bit, then maybe try a skirt with flats, less dressy top, and casual accessories and slowly ramp up to dressier pieces as people become more used to seeing you in skirts. NY&Company has a fabric that looks more like denim that I think is called called “hidden blue” and I’ve seen both skirts and trouser jeans in the fabric. It seems like a good choice to use in the transition as well.

    • Leather Bag :

      Totally second adding a blazer to the jeans! Nordstrom’s Gibson Linen blazers are perfect for this.

    • Not a lawyer :

      Start slowly; every day adding increasing the importance of “business” in business casual. Pencil skirts, more structured tops, blazers. Classy statement jewelry may help (think sheath dress + simple statement necklace). If you must wear jeans, add skinny heals and a blazer.
      Oh, and have shirts pressed! Nothing says I’ve got it together like a well-pressed shirt.

  2. Leather Bag :

    So, I purchased the bag featured here last Thursday. It arrived yesterday and is gorgeous and the perfect size. However, it smells fishy – as in, like fish. I assume that the leather was treated with fish oil, but of course that’s just a guess. Any suggestions for how to get rid of this smell, since I really want to keep the bag?

    • Wow, that is really weird. I have never heard of fish oil being used to treat leather. I would see if you can exchange it because a bag really isn’t supposed to smell like fish and I would be very surprised if all these bags smelled that way.

      • I just googled this and apparently this is actually a thing. Gross!
        I would still try to exchange it, maybe you just got a defective one?

    • Fill it with coffee beans and hang it outside?

  3. In addition to a watch, i’d suggest only wearing high-quality pieces of clothing and jewelry. Thing substance. Since Reader U doesn’t have to spend a lot on clothes, shopping sales and buying high-priced pieces on sale or close-out will also help her stand out and without spending a fortune.

  4. On a similar note, can anyone recommend a moderately priced “summer” skirt suit? TIA ladies. :)

    • Lord & Taylor has a bunch of skirt suits on sale right now, but many in lucky sizes only.
      This one is available in lots of sizes though and is $104 less an additional 15% off. Not sure what you had in mind with “summer suit” but I feel like this one has a good warm weather feel to it.

  5. Olivia Pope :

    Pencil skirts are excellent for this. Ponte knit pencil skirts are comfortable but formal looking, if you want to step it up without wearing a suit. Blazers also ramp up an outfit.

    Kat’s advice to buy a ponte knit suit is a good place to start. Then, I would find high-quality resale store in your area to supplement. Clothes mentor is a resale shop in 25 states, and I bought work clothes there for very reasonable prices (e.g. $6 for a Banana Republic work appropriate top).

    • Orangerie :

      +1 to ponte knit pencil skirts. Loft makes a great one that I’ve picked up on sale in a couple colors for roughly $30 each.

    • Thank you for the Clothes Mentor recommendation! I’d never heard of this store and there’s one along my commute. I will definitely check it out!

  6. I know the LW said she doesn’t wear slacks, but I think the one first step I’d take here is to replace the jeans with a tailored trouser. There are a kazillion options, as a petite woman myself I prefer the J. Crew cafe capri, but the BR Hampton (also petite) or Anthro Charlie pant are good options as well. Next, I would work blazers into your wardrobe as much as possible, over dresses, instead of cardigans, anywhere you can. I think a blazer signifies authority more than any other women’s wardrobe item. And then, like the previous commenter said, look at stepping up your accessories, a good watch, or classic bag can go far.

    • This is good advice. Or you c0uld do skirts & button down shirts. In general, I would look at some places like the banana republic website. I think they do “casual dressy” very well. There are always those people who look dressier than others no matter what; I would try to emulate them. Part of the look is always having things perfectly tailored, pressed, neat, to wear things with more structure, etc.

    • Pants just don’t work for some people’s bodies. I have spent probably close to 20 years (and I’m only 35) trying to find khakis that work for me. They all look terrible no matter how many different fabrics, cuts, or designers I try. Jeans, no problem. I can even find wool dress pants occasionally that work (although that’s still a tough one) but cotton pants are a nightmare. Overall, skirts just work way, way better on me. (And I promise that if you met me, you would think I was pretty normal looking. Nothing freakishly out of proportion. And yet, no khakis for me.)

      • Merabella :

        Khakis are the Devil’s play thing. I have NEVER ever been able to find cotton pants that look good on me. They make me look like the Michelin man. Skirts all the way, and dresses.

        • Khakis are dreadful and are unflattering on most bodies – even people who have bodies that are easy to dress look better in Not Khakis.

      • Maybe because khakis are just abominable in general. I sympathize with women who have to wear them as a work uniform, but otherwise I really think there is always a more flattering option.

      • Me too! What is it about khakis? I’ve tried on hundreds, they never fit right.

      • WorkingMom :

        Try a tailor! You might be able to find a pair of dress slacks that fit *almost* perfect, then take them to a tailor and he/she can make it a perfect fit! Same goes for the OP, sometimes middle-of-the-road items (not designer but not big box store, think J.Crew outlet) tailored to fit your body perfectly can make you look & feel like a million bucks!

  7. Semi-thread jack: I am about to transition from a mid-level position at a university in DC (business casual most days, a little more formal for meetings) to being a full-time PhD student in LA. Everything I own is either not weather-appropriate, too formal, or too boring for my new life. I don’t want to stand out as the “Ann Taylor type” when I go back to school, how can I freshen my wardrobe on a budget?

    • Former grad student here. To give some context, I was in the humanities at a very competitive school (not showing off, just giving context). My colleagues wore khakis, corduroys, jeans, sweaters, oxfords, t-shirts, cardigans, scarves, Birkenstocks and Chuck Taylors. So, yes, the stereotype.

      I wore minimal makeup (lip gloss, blush mascara), good fitting jeans or a casual skirt, top and cardigan and comfortable flats or boots.

      In my experience, dressing down in academia is a good bet. Otherwise we wonder if you really need your stipend and grant money. There was a great site called Academichic or something. They address way more than I can in a small post.

    • Does the department have an annual picnic or something? Maybe you can google for photos and see what everyone is wearing.

    • Actually I think your experience in dressing more formal could be helpful in academia. Just graduated and most grad students (myself included) did not really seem to have a handle on how to dress well for events like conferences etc. That’s part of the reason I started reading this site. Granted, I work in the sciences where you don’t want to mess up your best clothes in the lab, however on some occasions stepping it up would be nice.

      Avodah’s suggestions above are good and will not break the budget. For shoes, you can find comfortable options in leather if you will spend most of your days on your feet. I happen to like Clarks although some styles can look stodgy. You can also try dressier sneakers as opposed to running shoes for example. Don’t get rid of your blazers you can still use them or you could find more casual options. For bags, I carry a backpack which holds laptop and a handbag. If your laptop is light, you might consider a nice tote which holds everything. Or you could do a small handbag and a nice looking backpack. I also think the environment defines the style. I am in a big state school in New England, the style here is way more casual and less trendy than say NYC or Boston would be. So, I’m sure when you get to L.A. you will gather more inspiration from the people around you. In fact I dare say you can be more daring with your style (but not over the top) since there are such few rules in academia.

    • I am a grad student in LA, and since moving here from San Francisco 6 years ago, I have probably completely turned over my wardrobe. People in LA dress casually but usually not preppy.

      If you feel like you your current wardrobe is too preppy for LA, I would say “deconstruct” your current clothing first. Meaning, rather than wearing the matching cardigan and shell of a twinset, wear the cardigan with a shirt in a contrasting color, white or black, or the same color but a different shade. The modern “j crew” preppy is popular in LA, which is preppy elements with modern silhouettes (like slim pants) or contrasting colors or patterns that still go together (actually pretty tough to pull off) with oversized glasses and bright lipstick.

      Honestly, I would save your money to shop when you get to LA. People in LA get rid of a lot of nice things, so resale places (like crossroads or buffalo exchange) can often have a lot of stuff. Also, the summer get HOT, and unlike DC, people dress like it is hot outside (skirts, maxi dresses, shorts, sleeveless shirts).

  8. Orangerie :

    This is the skirt:

  9. You’re going to have to do this your way. Find clothes that make you feel authoritative and then tailor them to a business environment. Confidence is more important than any clothing item when you are looking to move up (unless there are serious issues with your wardrobe).

    I *wish* I could wear button down shirts because I think they look so powerful and crisp, but I don’t feel comfortable in them so they don’t get me where I want to be for big meetings.

    Adding to the recommendations for ponte, skirts especially. I could live in ponte skirts.

    • Yes! Thank you! I was wondering if I was the only person who feels like she just can’t pull off a button-down shirt.

    • Same here, I love the look of button down shirts but for me they usually get creased up by day end and also looks very frumpy from the back when tucked in. I feel like it looks so much more polished for guys or women on tv, I can never pull off that look.

      • I’ve debated whether to get one of those body-suit type button downs that VS sells, seems like that would be the only way to achieve the polished look. but i think i’d feel a little ridiculous wearing one :)

        • I debate it too! But, as from my experience with most VS clothes, I’m pessimistic that it will just look cheap.

        • Katie Anne :

          I own two of those (one black, one white). I have constantly looked for other places to start making something similar so I could avoid the ignominy of buying business attire from Victoria’s Secret… but to no avail. I do like them though. The quality is higher than probably most other things that VS makes. For me, they actually solve the busty-girl gaping problem – keeping it tugged down in front means that it’s just overall smoother in front. My caveat is that they have snaps at the bottoms of the body suit which can be sort of uncomfortable – digging in to you in a somewhat unfortunate place. But if you’re curious, give it a try – they are not my absolute favorites but they are definitely in the rotation of things I wear frequently.

      • The reason that TV people look awesome in clothes that look stupid on normal people is that EVERYTHING is tailored to fit their body exactly. Even t-shirts are altered to be the most flattering possible. So unless you have a personal tailor who follows you around, evaluating the fit of all your clothes and making alterations as needed, it’s an unreasonable standard. :)

        • They can also put on a new shirt between takes if the one they’re wearing gets horribly wrinkled.

          A couple of summers ago, I started paying close attention to the men I saw walking around at the end of the day and I noticed you can always tell if someone’s been wearing a dress shirt for hours. Even if the shirt is starched, the back is pretty wrinkled by 5:00.

    • i hate button downs! :

      I have the same problem. I look uncomfortable and stiff in cotton button-downs, and prefer silk blouses (with or without buttons) if I have to dress that formally. My theory is that button downs work on people whose bodies are proportioned well for button-downs. Flat stomach OR bigger ta-tas and not too much difference in waist to hip measurements, I think.

  10. Related questions:

    I am starting a new job this summer. I’ll have about a month off beforehand. I am excited to start work and also excited for the time off!

    My 1st question is– what would you buy to vamp up your wardrobe for a new job? This is my first “real” full-time job. I have a wardrobe full of law school internship clothes but I want to step it up a bit… thoughts?

    Second (unrelated but fun) question is: any professional/life advice for transitioning from school to work? this is my first real, full time job after years and years of being in school…

    • To your second question: Observe everything. Spend a lot of time looking and listening and figuring out how things are done. Ask questions, but only after you’ve used the resources available to you to find an answer. When in doubt, be quiet. No one will remember what you say in your first months, except if you say something dumb or inappropriate or talk too much. That might be controversial advice, especially to a woman, but I mean it only in the very early going, while you’re assimilating. Listening is so much more important than talking!
      Also, be patient. It takes *at least* six months to get used to a new job, and often longer. You might feel like an idiot or an imposter or overwhelmed or overworked, or all of that . Ride it out until you get through the break-in period. Even in great jobs, there’s often an adjustment period, and it’s important not to panic.
      Good luck!

      • +100 to “observe everything.” I am an observant person by nature and it has served me very, VERY well in the business world. I know that Bigwig Y likes to be addressed as Robert, not Bob; I know that Partner B is a stickler for grammar and powerpoint formatting. I know Linda over in sales will FREAK OUT if someone changes the formatting in her presentations. I know how to kick people out of a conference room without being rude. And I remember everything.

        You’d be really, really surprised how many people go about their jobs in a bubble.

        If someone asks you a question, you probably won’t know the answer. That’s ok. Tell them you’ll find out for them by X, and hunt that answer down. Don’t just send them looking elsewhere.

        Figure out if most people bring lunch, or buy lunch. I’ve worked places where those that brought lunch (or brought lunch and ate at their desk, not the cafeteria) were left out of the loop because so much work got done over the tables in the cafe.

        Introduce yourself. Finish the introductory convo by repeating the person’s name, “looking forward to working with you, Jane.” If your office is big, either make sure to ask for last names, or see if the company has a “facebook” for employees. That was my bible for a while!

        When you’re sent to someone to get something done, try to learn how to become “self service”. Example: instead of asking the same sales ops person to run a report for you every month, ask if it would be easier for you to do it yourself (assuming the person in sales ops is slow and often forgets, which mine does). The old “teach a (wo) man to fish” mentality.

        Stay politically neutral and avoid office gossip. If you can’t say something nice, shut up. It’s OK to listen to others complain (if you can tolerate it), and it’s nice to be well informed, but don’t contribute to the gossip.

        If you’ve got nothing to do, ask for more work in an area you’re interested in. Don’t get yourself pigeon-holed in your role, esp. if you’re entry level.

    • Katie Anne :

      My recommendations for coming out of school mostly have to do with how you interact with the work you’re being assigned. In school, you get given an assignment, you do it independently, and then hand it in for a grade. But your “assignments” can be a little different at work, depending on your industry. My advice:

      1. Keep people posted on the things they are interested in. If I’m working on something for someone, or I know that my director is particularly interested in a project I’m doing, I’ll drop a quick line to them, even if it’s just to say, “Hi, just wanted to let you know that this is still on track. We are currently doing xyz and the estimated completion date is xx/xx/xx.” I often do this at the end of the week via email. This also serves the purpose of letting people know sooner rather than later if there are problems or delays. This was a weird transition for me coming out of school, where I would get assignments completed and only reach out to a professor with questions / concerns.

      2. Follow up on projects after they’re finished. I typically aim for at least one “formal” and one “informal” check-in. By formal, I mean I send an email or set up a meeting to confirm that everything is completed and that they don’t have follow-up questions or concerns. By informal, I try to remember a month or so later to casually ask about the project if/when I see the person; i.e. “Oh hey, is that report still meeting your needs? How’s that going?”

      3. Find work! This is always a tough one – people say “you should be seeking out things to do” but it’s kind of difficult to figure out how. If you need more work, here’s my advice on how to get it: go to meetings and listen for the phrase “WE SHOULD”; i.e. “we should create some documentation around this” or “we should probably reach out to them”. If you hear a “we should” that sounds like something you can do or would be interested in, pounce! Most people say “we should” to mean “someone other than me should”. If it’s appropriate during the meeting, say “I can take follow-up on that.” If it’s not appropriate (know your office), reach out to your manager afterwards and say, “Debbie mentioned she’d like someone to create some documentation; I would love to work with her on that, what do you think?”

  11. Related… How are pencil skirts / skirt suits supposed to fit in a semi-professional environment? I’m fairly curvy, at least on the bottom, and in my mind any skirt that curves along with me is too Mad Men for the 2013 office. I guess my ideal is a skirt that tapers to my knees in a STRAIGHT diagonal line, but that’s sometimes hard to manage.

    I’m asking because my boyfriend and best friend both disagree with me on what constitutes “unprofessional.” (Then again, my boyfriend works in a very casual environment, and my friend things that visible bra straps and scuffed shoe are “totally fine.”) So, HELP PLEASE. Especially with photos of “good” examples, if possible.

    • Was wondering that very thing this morning when I put on a new pencil skirt. My view (and I work in BigLaw, so pretty conservative office) is that some curve is ok — it doesn’t have to go to your knees in a straight line — but not total curve, if you get my drift. In other words, it’s ok to follow the curve some, but the fabric of the skirt should not be touching the back of your thighs (at least at the top of them).

      • I think it should skim not hug your body. So, nothing Kim K would wear. If it looks like it’s pulling or whiskering, it’s probably too tight and you should size up. I think this is a pretty good example of “good” pencil skirt:

    • Maybe just go with an a-line skirt? I have one from Banana that doesn’t get too tight where I gain weight (…in my rear). No pictures, sorry :(

    • oil in houston :

      in the same way some people above can’t wear khakis, I can’t wear pants nor pencil skirts, it looks way to ‘joan’ on me (to use your reference :)). So I stick to a-line or full skirt, a nightmare when I need a formal suit, but thankfully my office is business casual so I wear mostly separates.
      I like boden, as well as eshakti although their quality is a bit hit and miss. Talbots does nice things as well.

    • Midwest Transplant :

      I have quite the curve on the bottom, and in my ideal world a skirt would fall straight down from the largest width. However, in reality, I have generally wear skirts with a slight hug at the bum, because even with taking everything in at the waist, I just have that issue. I think this fit is perfectly professional:

      By the way, that is a great skirt too!

    • I have a similar body type, and I find that the proportion of a pencil skirt looks best when it hits at the bottom of my kneecaps, not above or in the middle. And definitely skim the curves, don’t hug them. I often size up and let the waistband hit a little below my natural waist, which also helps de-emphasize my hips and booty, because the waist-to-hip ratio isn’t as severe.

      • Oh, and one more pointer: if there’s a slit in the skirt, it should never gape open when you’re standing still. Never.

    • I have a curvy/athletic lower half, and I have to tailor all my skirts. I get the best results when I buy a skirt that sits comfortably- neither too loose or too tight around the widest part of my lower body. I then ask my tailor to take in the waist, such that it is a tad bit snug. (This helps with the rotating skirt issue and keeping skirts tucked in.)

      The final result should have a little shape but still leave something to the imagination. Personally, the Duchess of Cambridge is my style crush, and I think she wears pencil skirts quite well. If there are creases across the hips, it’s probably too small. If the skirt is too big, it will visually add pounds and do nothing good for your image.

      Side note- there is an HR girl at my office who has managed to violate every corporate dress code rule ever written. She has one pencil skirt, and it is tight enough that it touches the top of her thighs. On top of that, it has a slit in the back that goes halfway up her thighs. She wears them with knee-high boots, skin-tight turtleneck, and an obvious fake tan. At least she doesn’t pair the skirt with her open-toe leopard print stilettos. She saves those babies for skinny jeans or leggings.

  12. This looks really pretty, I always where dark colours for work stuff, but the other day I wore a red dress at a corporate event and I felt amazing.

  13. I think the recommendation to add blazers to your jeans is right on point. Even more casual blazers will make you look more authoritative & professional than jeans and a top alone, and it’s not too much of a step up from what you’re already wearing that it will make you seem out of place.

    I’d also reevaluate the quality of your jeans – definitely nothing ripped or faded, and I recommend dark washes in a straight, boot or trouser cut. Black jeans might also be a good way to subtly up your look, with a non-black neutral or colored blazer.

    If you’re already wearing dresses to the office, I’d start wearing dresses more often. This might also be a place where Kat’s “sleekify” suggestion also applies – look for tailored silhouettes & substantial, professional fabrics over fuller skirts & cotton sundress-type dresses.

    And while I usually love most of Kat’s advice, a jean jacket or chambray shirt to look more professional? No thanks. I don’t think there’s a reason add more denim to your wardrobe, but I do think you’re fine dressing up the jeans you’re already wearing.

    • Lots to agree with here. Stick with “nice” jeans, especially in darker colours. Add blazers. Wear more dresses if you already wear them, but if you normally don’t more than a few times a year you might get comments if you start wearing them regularly. Sleek is good. Jean jackets and chambray shirts have always seemed really informal to me, more so than jeans.

      Beyond that, I’d say step up slowly, if the timing allows. If you normally wear your more “formal” stuff a couple times a month, go with that level a couple of times a week, and simultaneously upgrade your current “formal” to a higher level. Over a few weeks (2-4), get to a point where your current “formal” is your new normal, then step that up.

      Find suiting pieces you can wear as separates, but only wear them together for the more formal occasions (special presentations, interviews, etc.). Go from golf shirts to (well-fitted) button-downs, cardigans to blazers, and get some spiffy shoes and statement jewelry, but don’t upgrade all elements at once – it can look suspicious. Above all, make sure everything fits properly.

  14. I also work in a very similar, casual office. Even though other people wear jeans and tank tops, it’s important to me to feel somewhat polished. I usually stick to black skinny jeans (white in the summer) or blue trouser-style jeans as opposed to ripped or washed out denim. I’m also not a slacks girl, but I do like J. Crew’s minnie pants, and also have a pair of silk pants that I love. Up on top I either wear a casual blazer or cashmere cardigan with a simple tee, or I’ll wear a really nice silk blouse on its own. With the warm weather coming I am looking to invest in a vest/sleeveless blazer, silk dress, and nude blouse. I agree that investing in a few pieces in quality fabrics and neutral colors can really elevate your wardrobe!

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