Workplace Style Thoughts: Dresses and Skirts

My favorite work dresses before the pandemic. Currently, they don't suit me as well as they used to.

Now that I've been back in the office full-time for several months, I've been thinking a bit more about the continuing development of my workplace style. 

When the New York state government first allowed nonessential offices like ours to reopen last July, my office switched to a casual dress code for the time being. There's still no indication my supervisors have any interest in going back to our former business casual dress code, so in theory, I don't really need to think about my "work clothes" at all right now. But I actually do enjoy many elements of business casual clothing - though not business formal clothing, ick! - particularly in fall/winter, so it's genuinely fun for me to think about some categories of work clothes. 

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Before I really get underway with today's post, please note that I talk about certain body shape and weight changes I experienced while social distancing and working from home due to COVID. I won't go into specific weight-related numbers, but may otherwise be quite blunt about some of the other changes. I know that's not everyone's cup of tea. 

On Work Dresses 

Prior to the pandemic, I'd developed a very set work uniform. I wore the same sleeveless or cap-sleeve dresses year-round, mostly plain sheath dresses. (Though I was also extremely fond of my  past-season secondhand J.Crew "Presentation" shift dresses with bow details in different colors.) My favorite work dresses were two fitted sheath dresses with little rectangular faux cap-sleeve details, the J.Crew "Resume" dress and another from Ann Taylor, with the J.Crew Presentation dresses as close second favorites. 

In spring/summer, I wore these dresses with light linen or cotton-blend cardigans, mostly from Uniqlo. In fall/winter, I wore these dresses with heavier sweater blazers, in particular the J.Crew "Juliette" sweater blazers (sample outfit), but sometimes with the mostly-discontinued "Sophie" sweater blazer instead (sample outfit). (J.Crew has debuted various other designs to replace the Sophie,  including the "Eloise," "Camille," and cocoon and classic styles.) I also had other types of dresses, sweaters, and jackets in my work wardrobe to cycle in to my outfits throughout the year to create some variety. I almost never reached for separates on business casual days, instead I pretty much always preferred to wear dresses. 

By late 2018 and until the world shut down in March 2020, I'd definitely settled fully into a very defined work uniform. Almost every workday throughout the year, my outfit would be one of the same work-appropriate dresses with a seasonally-appropriate sweater or sweater-jacket, shoes, and other accessories. 

Since I started returning to the office more regularly around mid-June this year - and while we still have a casual dress code for the time being - I've been slow to return to my old business casual wardrobe staples. I've only dressed in one of my pre-pandemic business casual outfits maybe four or five times, when I had important videoconference meetings with a client. I've also worn business formal only twice, for videoconference depositions. 

Part of the reason I haven't been reaching for my old business casual uniform is that, at least when I first started going back to the office in June, some of the items simply didn't fit well - or at all - anymore. Like many people, I gained weight during the pandemic from the sudden dramatic change in my lifestyle. I've been working on my diet and exercise, but in a slow and gradual way. It was only very recently that my body measurements got back to roughly where they were in the months before the pandemic. 

But some items I relied on most heavily before March 2020 still don't look the way they used to. I'm really seeing and feeling some effects from my lost fitness level and lost muscle mass, particularly around my shoulders, upper arms, and stomach. So even if my chest, waist, and hip measurements are now roughly where they were around March 2020, the J.Crew Resume dress and my Ann Taylor sheath dress with the same faux cap sleeve detail - both absolute favorites I used to feel awesome in - still don't look like they did before. Accordingly, those specific dresses definitely wouldn't be on my list of go-to items right now if I suddenly went back to wearing business casual all the time. 

As a result, one thing I'm really thinking about lately when it comes to my work wardrobe is dresses with different silhouettes or designs that'd suit my current body better and would generally be more forgiving of future body shape changes than closely fitted sleeveless sheath dresses. That's why I first became interested in those Reiss Lara dresses from September (likely cheapest at Selfridges, even with international shipping and duties). Those are definitely unlike anything else in my work wardrobe, and they have a forgiving fit in the chest and shoulders. Though it remains to be seen - once the weather cools down more in NYC - whether they'll be practical for me. 

One big challenge when it comes to shopping for more formal-leaning business casual work dresses is that the mid-range mall brands I historically relied on for this category - Ann Taylor, Loft, and J.Crew; I never liked Banana Republic for my body shape, but they're also in this niche - are mostly no longer reliable places to shop for these dresses. Back when I first started looking for work clothes around late 2013, while I was still in law school, those stores always had a decently wide range of formal-leaning business casual work dresses available, including in the sale section. It was easy to get dresses like this for additional percent off sale prices basically year-round. 

This has changed considerably in the years since, in particular at Ann Taylor and Loft, because those companies - and this tier of the fashion market in general - have been struggling a lot in recent times. I've complained a fair bit about these changes at Ann Taylor and Loft because their dresses always fit my body shape the best off the rack. So not having them to rely on for future work wardrobe shopping makes things more difficult for me. Also, their extremely safe and conservative approaches to design, at least in past years - see this SNL skit or even this 2011 Washington Post humor piece - really... suit my workplace style sensibilities... even if it's not exactly aspirational to admit that. 

Anyway, I'll try not to shop for any more work dresses through at least the end of 2021. The Reiss Lara dresses plus the other dresses already in my wardrobe - even if I don't currently love the look of the J.Crew Resume dress and similar Ann Taylor dress on me, they technically still fit, and I'm fine with my other old dresses - are more than enough for my current needs. I'm intrigued by some of the dresses made by The Fold London, but I've seen many comments from people who've tried on their clothes which suggest that The Fold's designs may not suit my somewhat top-heavy and busty 5'3'' frame. 

Also Seeking One Really Great Skirt

Longtime readers may recall that skirts can be a tough category for me. My most memorable shopping mistakes since I started keeping this blog were two similar Uniqlo skirts I bought in the same month and proceeded to almost never wear before sheepishly sending them off to ThredUp. Since then, I've been far more cautious about shopping for skirts. Even though I did eventually find a wrap skirt I really like from Uniqlo, I admittedly don't wear it too often because I almost never reach for separates for work, or for casual wear during the summer. 

Skirts can be particularly difficult for me to shop for because of some of my body shape insecurities . Although I sometimes put together outfits with tops tucked in to higher-waisted skirts or pants, I generally don't like the look of tucked-in tops at all. I feel like it usually ends up making both my bust and waist look larger than they are. That feeling is exacerbated even further if the skirt puffs out too dramatically from the waistline. 

It's also best for me if a skirt has an adjustable waist - like with the Uniqlo wrap skirt - or if the waistband is stretchy or otherwise a bit forgiving. I have a softer tummy and some tendency towards size fluctuations there throughout the day, e.g. if I drink a lot of water or have a big meal. In other words, anything with a really snug waistband meant to hit at the smallest part of my natural waist has some likelihood of causing fit or comfort issues. (For some reason, I've always had a much harder time with fit issues at my waist with skirts than with pants. But maybe that's just because I rarely wear non-stretchy pants, all my jeans certainly have had some stretch to them.)

Even with all my issues with skirts, I really do like the idea of finding one really great and more formal-leaning business casual skirt that makes me feel fabulous and beautiful. It's hard to find a photograph that really illustrates what I have in mind for this ideal skirt. Nothing I could find on any of my Pinterest style inspiration boards was an exact match. I did my best to select a few photographs that were at least in the ballpark of what I'm thinking about, though these skirts or outfits above are not the exact color scheme or type of look I'd prefer for my "perfect" work skirt and its associated outfits. 

What the photographs do have correct-ish is that I'd like my really great skirt to be midi-length - that's what I like best for myself and my proportions - and to have either a wrap skirt look or at least be asymmetrical or with a slightly draped look to it. I'd also like the skirt to taper or flare out gently from the waist, and for it to look like it makes sense to wear the skirt without tucking in my top. (So no prominent belts or ties or other big details at the waist that won't lie smooth and flat under a top.) I don't really have an exact color in mind, but probably something more neutral than the bright blue skirt pictured above. Also, my ideal work skirt probably shouldn't be black or an overly dark gray, since that might look too heavy or monochromatic when combined with my black tights and my mostly black leather collection of fall/winter shoes. 

While Ann Taylor currently has some skirt designs that appear, at first glance, to fit at least some of my criteria, that's not the direction I want to look in. This isn't necessarily a problem with the brand, but I owned a slightly absurd number of non-suiting Ann Taylor skirts in law school and my first years in the legal profession - all purchased before I started documenting my fashion shopping on this blog in January 2015; thus, they were also all from before I understood my personal style preferences - and in the years since, I've decluttered all of them from my closet one by one, mostly by sending them to ThredUp. Those skirts were all work-appropriate and fairly conservative, "safe" designs, and all were reasonably durable and good quality. But they never made me feel particularly good or excited to be wearing them. I want to really love wearing this one great skirt.

It's really hard to say what my ideal work skirt will ultimately look like. I feel like I've gone through TheRealReal's entire selection of skirts in my size - and anywhere remotely near my price point - without finding anything that jumped out at me as being something I even wanted to order and try on. In the product widget below, I've selected a few skirts currently available from various retailers that have at least some of the elements I'm looking for. But you'll see that many of them don't fit all my criteria, and others are so dramatically expensive I obviously could never actually buy them, even at 50% off. 

I think my favorite of the skirts in the product widget is this Tibi skirt in black and white plaid. Tibi is not a brand I'd normally look at much, as I think most of their designs are far more adventurous and fashion-forward than my personal style preferences and lifestyle can accommodate. But after learning more about the brand and about Amy Smilovic, their head designer and founder, and her views on personal style, I've become really intrigued by some of Tibi's designs. (I first learned about Smilovic through Kathy's blog and some of the comments there.)