My Wardrobe, Myself

I recently had a medical procedure done to address the varicose veins in my left leg (the right leg will be taken care of later in the year), which led to my needing to wear a compression stocking for several weeks. This procedure also resulted in my leg feeling quite sore and tender, so I was unable to wear some of my usual clothing comfortably.

In the early days, I mostly wore loose-fitting joggers and yoga pants and didn’t schedule many social activities that might require other types of garments. But for the few out-and-about engagements that I had, I struggled to get dressed. In today’s post, I share about that experience and ponder the notion of what is and isn’t “dressy.”

My Standard “Uniform”

My usual “uniform” during the cooler months is to pair a long-sleeved top with jeans and either a cardigan or jacket. This works for my casual lifestyle and the types of activities that I do (outside of my regular walks, when I wear athletic clothing). In the summer, there’s more variety to how I dress, as I switch out the jeans for cropped pants and sometimes also wear dresses or skirts.

In terms of full-length pants that aren’t either jeans or athletic pants, all that I own are black pants. This is because I like wearing jeans, and I also haven’t been able to find other full-length pants that are both casual and have a long enough inseam for me. Many retailers that offer tall sizing still have limited options, and they’re usually only what are considered “basics,” like jeans and black pants (and perhaps a few varieties of dress pants).

So, when I first needed to wear something other than jeans or athletic pants during my recovery (which is ongoing), I pretty much only had black pants to choose from. The weather is still pretty cool where I live, especially in the evenings, so I wasn’t ready to switch to cropped pants and open-toe shoes just yet. I thought it would be easy to just swap out my usual jeans for the black pants, but what I discovered is that I ended up feeling too “dressy” in the resulting outfits.

On my first such occasion of experimenting with the black pants (which I usually only wear for my very rare dressier outings), I tried on multiple variations of tops and toppers, but none of the ensembles felt casual enough for where I was going. Eventually, I ran out of time and just had to go with the best of the looks that I tried on, but I felt overdressed all evening long. Even after I came home and played in my closet some more, I still ended up feeling too “dressy” in whatever outfit I put together.

Dressing Down Black Pants

Now, I can think of a few ways to dress down black pants, such as pairing them with a denim jacket or another ultra-casual type of topper, but I don’t own such pieces. My recent experiences with the black pants made me realize that many of my tops and toppers also read “dressier,” as I prefer to wear darker colors most of the time. I rely heavily on denim bottoms to tone down the dressiness of my ensembles, which hasn’t been much of a problem until now.

I’m not exactly sure why darker colors look dressier, but that’s what I’ve noticed about my wardrobe. Of course, the style, silhouette, and fabric also play a role in how casual or dressy an item appears. But since I tend to prefer more classic or minimal styles, those types of pieces also look more upscale or dressy than many trendier, “boho,” or sporty styles.

Another way to dress down an outfit involves the shoes we pair with it. The recent trend of wearing sneakers with almost everything automatically makes an ensemble appear more casual. But as you might have guessed if you’ve been reading my blog for a while, that’s not a trend that appeals to me. I only really wear sneakers with athletic wear or “athleisure,” and most of my other footwear is also on the dressier side. During the cooler months, I almost exclusively wear boots, and the boots that I like to wear are streamlined and sophisticated rather than rugged or casual.

The Way I Dress is Inflexible

I’ve figured out a way of dressing that works for me, but I now understand how inflexible it tends to be. As long as I’m wearing jeans, I’m able to pull together looks that work for my casual lifestyle. But once denim is off the table, the whole thing collapses like a house of cards! I immediately find myself in dressy territory, and I struggle to leave that zone without my tried-and-true jeans.

This whole phenomenon reminds me of years ago when I struggled with what I termed “church lady style,” in that most of my skirt outfits looked like something I might wear to church or another similarly dressy occasion. That was because of the types of skirts that I was wearing (as well as many of my shoes and toppers). Even when I paired the skirts with casual tanks and tees, I still looked like I was headed off to a worship service. Not that there’s anything wrong with appearing that way, but it’s not the best when your target activity is much more casual, such as running errands or having lunch or coffee with a friend.

It took a major style shift for me to leave the church lady aesthetic behind, but I actually wanted and needed a sartorial change back then. The difference now is that I’m mostly happy with my jeans outfits, but I’ve come to understand the inflexibility of needing denim bottoms in order to dress appropriately for my lifestyle. I don’t want to give up the jeans, but I don’t want to be so dependent upon them, either.

I Don’t Know the Answers to This Style “Pickle”

I’m not sure what the answers are to this bit of a “style pickle” in which I find myself. I’ve already been able to return to wearing jeans again, as my leg is healing and doesn’t feel quite so sensitive and tender. So, there’s no real sense of urgency here about the black pants and how they seem to automatically render an outfit “dressy.” However, I feel that it’s interesting and potentially helpful for me to explore the “dressiness” dilemma and how I might be able to solve it.

I don’t like feeling like I’m overdressed for the occasions of my life, especially since I already tend to “dress up” more than most people in ultra-casual Southern California. I came to understand years ago that I don’t feel happy in the t-shirts, jeans, flip-flops, and sneakers that are commonplace around here, and that I need to instead wear what feels true to my own personal style aesthetic. But I also don’t want to veer too far away from the mainstream, as that makes me feel like I stick out like a sore thumb (which is never the way a strong introvert wants to feel).

Your Feedback?

I’m wondering if this is just a “me thing,” or if others feel the same way about the “dressiness” of black pants – and black/dark clothing in general. I’m going to continue pondering my “selectiveness” about the way I dress and how flexible I’d like my style to be, so this post was more about insights and questions than answers.

But if you have advice for me or would like to share your own experiences with navigating the dressy versus casual dilemma, I’d love for you to weigh in. Would buying a denim jacket (or perhaps a denim duster) solve this whole problem for me, or will it take more thought and effort than that? I’m open to whatever it might take, but I’d ideally like not to have to do a lot of shopping to make black pants work better for my lifestyle.

This is a wise and innovative group here, though, so I trust that some of you will have words of wisdom for me and anyone else who has found that black pants seem to equal “dressy.” I look forward to reading what you have to say. Also, if you have your own struggles with looking either too dressy or too casual, feel free to share them, as I’m sure others will be able to offer helpful advice.