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 …
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 alreadypretty.com. See Already Pretty’s disclosure statement for more details.