Reader Request: Moving from Casual to Business Casual

change style from casual to business casual

Jenn threw this one into the Suggestion Box:

I would love some tips and ideas for transitioning into wearing business casual and more heels/pumps/dressier shoes. I’ve been a stay-at-home mom for 2 decades – and most of my “dressing up” has been for church or military functions. On a daily basis, I normally wear casual clothes – because doing errands, cleaning, volunteering, and taking care of my children (6!) requires casual (but no pj’s or yoga pants allowed – my rule).

However, I am starting my master’s in education and will be student teaching and teaching for real soon – all which require business casual every day! How do I make the transition without feeling overdressed? Especially in the southwest, where super casual is the norm (seriously – people wear shorts to the opera and theater here!)? I love to wear heels/pumps, but I always feel overdressed…

So Jenn is thinking shoes, but also looking at a shift in her daily clothing choices and dressing habits, too. Since she’s in an environment that skews very casual and is worried about feeling overdressed, I’d recommend she do some mental prep for any clothing commentary that might come her way. Not a bad plan for anyone on the brink of a distinct change in personal style, as you never know who might pop out of the woodwork to ask questions or give opinions!

But if virtually everyone in her area is going super casual to everything, here’s another plan to consider: Arrive for those first few days of student teaching in smart business casual, and take the sartorial temperature of the environment. Maybe business casual will be too dressed up for that workplace and a drastic shift won’t be necessary.

But assuming that school advisors have suggested a business casual dress code or peers have recommended the same, here are a few tricks for easing into the shift from super casual to slightly dressy:

Identify some inspiration

Peruse Pinterest, flip through a few catalogs, bookmark a blog or two. If you’re building a business casual look from scratch after spending years in nothing but casual duds, keeping some inspirational images on-hand will help you feel focused. Who dresses how you wish to dress? What items do they wear that you already own? Any key pieces that you might want to purchase? How do they style and accessorize their outfits? That last one allows me to segue into …


Many super casual outfits lack intentional accessorization, so consider focusing some energy on those all-important finishing touches if you need to start dressing dressier. Many of the basics from your casual wardrobe may be able to migrate over: Solid colored tees and tanks, dark wash jeans, cardigans and pullovers, even a few basic dresses. An easy way to make those pieces look more sophisticated is to add belts, scarves, jewelry, hosiery, and other accessories. This older post on how to make simple outfits sparkle shows some great examples of how adding accessories can completely transform a seemingly plain group of garments. You may want or need to purchase a few new accessories, but overall …

Don’t shop

OK, that’s harsh. But don’t feel obliged to run out and purchase an entirely new wardrobe. The transition from casual to business casual is a bit easier to do than the transition from casual to corporate or vice versa. As I mentioned above, much of what you already own may be ideal for the outfits you now need to assemble and wear. As you peruse inspirational images, you may land upon a few key pieces that you’ll definitely need to acquire, but before you go on a bona-fide spree give yourself some time to live inside your new look. This will help you pinpoint items that will be truly useful. Even if you keep garment purchasing to a minimum at first, you’ll probably want to …

Invest in comfortable, quality pumps AND flats

Jenn asked for shoe advice, so here’s my main thought: Pumps are generally perceived to be dressier than flats, but most women cannot and will not wear pumps all day every day for a job that requires lots of standing. So pick up a quality, comfy pair of pumps … and a quality, comfy pair of flats. I recommend Clarks to virtually all of my clients plus everyone who asks for good, comfy pumps. They’re classic without being showy, they’re sturdy, and the styles the company puts out generally go with everything. For flats, try Naturalizer or Born. Buy versatile neutrals – black, cognac, and gray are all good bets – so these shoes can work with a variety of outfits.

If transitioning to dressier footwear feels awkward, try a few crossover outfits: A cute top, jeans, and the pumps for a weekend outing or a casual jacket with a dress and the flats. Break them in a bit before wearing them to work. In fact …

Practice with crossover outfits

Before you dive into a new job, environment, and set of dressing norms, practice a little. Don’t feel obliged to wear business casual while playing messy games with the kids, but if you’ve got errands or less active tasks on the docket for the day, try a crossover outfit like the ones listed above. Work dressy footwear into otherwise casual outfits and adorn with accessories. Practice bringing dressy, polished elements into your ensembles so that you know what feels and looks good to your eye.

Discussions of work wear are always controversial because “business casual” means different things in different industries. Heck, it also means different things in different regions of this country, and in different parts of the world! So bear in mind that this post was meant to help someone moving from casual to business casual in an environment where SUPER casual is the norm. Additionally, none of my advice posts should be considered gospel, including this one, and I fully expect you to read them with a grain of salt!

Images courtesy Nordstrom.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Originally posted 2012-11-09 06:12:48.

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15 Responses to “Reader Request: Moving from Casual to Business Casual”

  1. el Maggie

    Yesterday, I was visiting the place where I worked for the first 2 years of my career, and thinking about how much more polished I dress now than when I started out – and one of the big differences is having professional outerwear – nice coat, boots, bag, and hat that go together. Getting to a point that I never have to wear my ski jacket except for skiing was a big part of moving from my student wardrobe to my professional wardrobe.

  2. adorkable

    Depending on where in the Southwest, this may be very easy.

    I moved from NY to Los Angeles a few years ago, and the difference was pretty astonishing. In LA you can wear nice (emphasis on the nice) jeans, a button-down, and sandals with heels and you’ll be business casual.

  3. Susan

    I work in a super casual environment but business casual is more my standard. I have to say Sally has inspired me to work more skirts into my wardrobe and I find that is a BIG help in taking my casual wardrobe up a notch. This spring I found a great a-line denim skirt that I found to be so versatile that I really started keeping my eye out for more skirts in that style. I wear these skirts with flats mainly but if I’m not standing or walking I will wear a pair of wedges or a low heel and feel super cute and feminine! As always – thanks Sally!

  4. Lady Harriet

    I also made the transition from casual to the upper end of business casual this year. I found that several types of garments in my wardrobe can work for both. The first is fairly plain, dressier t-shirts. Nothing sheer or with printing on it, but plain or subtly embellished (e.g. a small ruffle around the neckline) shirts can be worn to work with something fancier over them. The other part of my wardrobe that has transitioned really well is cardigans. I always wore them a lot with casual clothes, but they work just as well over a t-shirt, blouse, or dress at work.

  5. Andrea

    Jenn, I also live in the southwest and I am almost always more dressed up than other people, but I get a lot of good feedback about it, so don’t fear the scorn of the shorts-wearing crowd. Sally was spot-on about accessories. A simple top and skirt/pants combo is elevated to a “look” with nice shoes, a belt, and a funky necklace. For a school setting, where you’ll be standing a lot, check out shoe brands like Sofft, Born, and Indigo by Clarks. They have a lot of fashionable mid-height heels that work well for business casual and should last a long time. Also, although I love dresses, I find that simple skirts seem less fussy and are easier to mix and match with an existing wardrobe. If you can find one or two relatively plain skirts in a versatile fabric (e.g. brushed twill, lightweight wool, ponte knit) I think that will help you a lot. Trim fitting cardigans also make me feel really put together without looking over-dressed (and they let me wear tops that might not otherwise be business-appropriate). If you’re in a warm climate, try cotton and/or three-quarter sleeves. Good luck with your new ventures!

  6. joann, sidewalk chic

    Because of grad school, I constantly have to toe the line from business casual to casual. I like your suggestions with the dressier shoes. I’m also a huge fan of the blazer/nice top/dark jeans combination — you can lose the blazer when you want to be more casual.

    • Sonja

      I want to second this, for me this has been a good formula. Wear dark jeans, nice black pumps, a black t-shirt and a blazer for work – take of the blazer and change into comfortable shoes, and you will look casual but still put together in an instant.

  7. Heather

    I love jersey dresses that are knee-length or just above. They are so versatile, can be layered over or under, mixed up with scarves, belts, or funky necklaces, paired with tights or leggings or bare legs, worn with a cardigan or vest or even a blazer, look good with sandals, flats, and boots, and still are very comfortable. I’m also in a town in the west where business casual tends to be very casual, and dresses like this are a staple for me to feel put together but not too overdressed next to my co-workers in jeans.

  8. Anon for This

    Specific to Student Teaching:: I would suggest that Jenn talks to her Master Teacher or the Student-Teacher program coordinator. In my program, although teachers can (and do) wear jeans, it’s not ok for student teachers to do so. We were provided with pretty specific dress-code requirements.
    Also, depending on the grade-level, heels and skirts may not be appropriate or comfortable. There can be lots of standing, sitting, climbing, sitting on the floor…etc.
    And finally – I’d invest in a nice comfy pair of athletic shoes for the days when you’re on duty or taking kids to P.E. You can always stash them under your desk/in your tote when it’s time for class – asphalt is murder on heels!

  9. Eleanorjane

    Good tips. Another thing I’d add is paying attention to grooming i.e. hair and a bit of makeup if you’re that was inclined.

    I’m kind of having to go the other way, having moved to a job where I work in a range of contexts from an office by myself (and walk to work, which affects my shoe choice), meeting other volunteers, other staff and representing the organisation. I’m still trying to work out what to wear…

  10. Trystan (the CorpGoth)

    The original poster didn’t describe her version of casual (T-shirts & jeans?) nor what level she’d be teaching (grammar school? HS?), so it’s hard to pinpoint how much she’d really need to upgrade her wardrobe. Bec. Sally’s “don’t shop” suggestion might be valid or might be totally off depending on those variables. I know a lot of SAHMs who, even if they don’t wear PJs, they don’t wear anything remotely like the casual-est of business casual 🙂

    But good wardrobe basics for a casual workplace, imo, would be knit dresses (Target always has tons of these; I’m wearing one right now), dark-wash or trouser jeans, cardigans, khakis or similar trousers, & better-quality knit tops (avoid thin fabrics). Make sure the fit is great, of course! These are all good for weekend wear too, so you can get plenty of use out of them.

  11. Olivia

    You mentioned the opera house so I’m guessing you are in the vicinity of Santa Fe. I’m from southern Colorado and have worn business casual since I got my first desk job at 16 yrs ago. For this kind of super laid back area, business casual is pretty simple: replace hoodies or sweatshirts with cardigans; jeans with corduroy, khaki, or knit dress pants with plenty of stretch; and for shoes pretty much anything except athletic shoes will work. Solid tshirts are fine. A button down is good, too, but that might get you the “Why are you so dressed up?” question, lol.

    I’ve just left my cubicle job after having my second baby and I feel overdressed around the other mothers at the playground, but these are the clothes I have and I don’t want to go shopping. I figure it’s better to be overdressed than under.

  12. Kristen

    When I was doing subbing and student teaching (elementary school level), the environment was as casual as business casual can go – wearing a skirt made me feel way more dressed up than most of the teachers (at two different schools). On a typical day I wore black or grey dress pants and a casual-ish shirt – no baggy loose t-shirts, but dressier tees, or sweaters, occasionally a button-up shirt, and black flats. I wore very small heels every once in a while, but mainly just the flats. I wouldn’t even go for comfortable pumps (personally), not when you’re standing for that many hours straight. Khakis were also a good choice, especially for a more casual day (instead of jeans). I had a pair of thin black denim trousers that I wore a lot too – they were nice looking, not like jeans, and very comfortable.

    You have to be practical with your clothing; elementary school in particular requires a lot of moving around, bending over, squatting down to desk level, etc and you need to wear things that allow for that. That said, as a student teacher especially, wearing more business-like clothes gives you a stronger impression of authority than dressing down. You want to make a good impression on the administration, other teachers, and the students, and you just have to find the right spot where everything lines up – your comfort level, the side of yourself you want to show off, and the environment of a particular school.

  13. Laura

    I actually student taught two years ago. At the time, I felt very young looking at 21, so I went to Ann Taylor and bought four pairs of dress pants: one kakhi, one black, one navy, and one brown. I then wore one of those pairs of pants with a button down, v neck tshirt and cardigan, sweater, or polo shirt every day with flats or one of two pairs of very low naturalized t strap heels (either black or multicolor brown/beige). I found this clothing recipe for clothes to be easy and practical for teaching elementary music. I also found that i was able to use a lot if the basic tees and accessories I already had. I wore a dress a few times and regretted it every time. However, if you are teaching a little less active class, dresses and skirts would be fine too.

  14. Heidi/The Closet Coach

    Accessories are definitely a big way to translate an outfit level from one to another. As you wrote, shoes are one, jewelry another; even adding a scarf can make a difference.

    I recently wrote on a similar topic and one other aspect I mentioned was fabric. Certain kinds, like wool or cashmere, instantly feel dressier than something like cotton. (

    If you’re a blazer wearing lady, that’s an easy way to add instant polish to any more casual outfit, too.