Life · mental health

Wtf Am I Supposed to Wear? (And Other Things That Keep Me Up at Night)


Perhaps it’s due to all the excess stress at work recently, but I’ve been having difficulty sleeping, despite the fact that I’ve been crawling into bed by 9:00 every evening. Early this morning, at the wee hours of 4:30, I was wide awake again. I gave up a few hours later, once Merlin decided that those lumps underneath the covers (aka my feet) were deadly enemies that must be destroyed. Truthfully, I was somewhat grateful for the excuse to get out of bed, having exhausted my mind with a major issue that has been haunting me lately…

What the fuck am I supposed to wear now that I’m 30?

You can roll your eyes at me if you want (I know I probably would if I was reading this), but this is a legit concern that has been bothering me lately, along with a few other key 30-something related issues. Remember last year, when I was panicking and having a major existential crisis over turning thirty? I look back at it and chuckle a little bit, because it really was no big deal. I’m still me, chugging along, trying to figure out who I am and what the hell I’m doing with my life. (I’m beginning to suspect that I will continue to feel that way on and off throughout my life and that it has nothing to do with my age.) Nothing major happened. Well, except one thing. Despite the fact that my eating habits have remained the same and I exercise regularly, I’ve noticed some small, but noticeable changes in my body. My metabolism has slowed and I’ve gained a few pounds. Only a few pounds. No big deal, right? But that’s where you’re wrong. Considering my 20 year battle with body image and eating issues, I didn’t handle this particularly well at first. I admit that I almost relapsed, due to that stupid little voice in the back of my brain that likes to troll me and tell me that my weight and appearance are important and are tied to my worth as a human being. Fortunately, I’ve had some time to adjust to my new 30-year old body and was able to pull myself off the edge of another downward spiral. Phew.

But, there’s still one problem.

I’ve noticed recently that some of my clothing is a little snugger that it used to be. It makes sense, as much as I want to rebel against it. As someone who detests shopping for clothing, I’ve put off fixing my wardrobe for as long as possible. I’ve reached a point, however, where I’ve grown tired of trying to squeeze my slightly larger hips and ass into jeans that were skintight to begin with, so I’ve had to begin shopping for new clothes. *Cue second crisis*

During a recent excursion to Hell, I mean, the mall, I all but had a complete mental meltdown. There really is no better place for it, after all, with all those bright lights and hundreds of staring, obnoxious sales people. (Just picture it: Me lying on the floor of the mall, sobbing and pulling her hair out as a kiosk saleslady runs over and attempts to spray me with free perfume samples.) Even my failed attempts to shop online have led to the same frustrating, confusing conclusion that I don’t know how I’m supposed to dress anymore.

Body changes aside, I’m not the same person that I was in my twenties. I’m successful at my job and work in a professional office setting. I don’t go out as much as I used to anymore. When we do go out we hang out as more relaxed, casual places, rather than loud, stuffy bars and clubs. I actually care about being comfortable now. Suddenly, all the tight, short dresses and high heels in my closet feel completely out of place in my life. When I’m not at work, I typically wear jeans or yoga pants with something comfortable on top. I wear flat boots and converse sneakers. I’ve started wearing my glasses all the time. But what am I supposed to wear to work? What about when I’m going out? My jeans, nerdy t-shirts, and cardigans are fine for when I’m hanging out at the bookstore or coffee shop, but what about the rest of the time? I’ve been struggling for years to figure out how I’m supposed to dress in the semi-professional/business casual environment at work that still allows me to express who I am. But, honestly, I’m not even sure what I’m trying to express anymore. Places like Ann Taylor and Banana Republic are too old for me. Forever 21 is too young. So where am I supposed to buy my clothes? Why is there no store for people like me? They can call it “Leggings & Lace” or “Mid-Life Moxie.” “Wine and WTF is On My Shirt?” Even if they had these stores, I still probably wouldn’t know how to dress myself, considering I’ve never been particularly good at these things.

Not long ago I got brave and added purple streaks to my hair. It’s on the underside and there are few of them. You can hardly even see them unless my hair is up and there is good lighting. Still, I know they’re there and I like them. I like my slightly funky, rebellious hair, even if nobody else realizes it exists. (Especially Boyfriend, who is colorblind.) Is it okay for me to have purple-streaked hair now that I’m thirty? I don’t know. Do my nerdy tees and converse sneakers make me look like I’m trying to be younger than I am? Again, I don’t know. How do I figure out the balance between being comfortable, but still looking professional enough for work? I DON’T KNOW. All I know is that I have a closet full of clothing meant for my 20-something year old self that don’t feel like “me” anymore.

I’m going shopping again this afternoon. Wish me luck.


12 thoughts on “Wtf Am I Supposed to Wear? (And Other Things That Keep Me Up at Night)

  1. While I don’t personally have some of these issues, wifey does so I understand. When I turned 30, I was still in the Army, so I always knew what to wear. But now, many years later I no longer have a uniform to wear. And, since I’m technically a “geek” stuck in the IT world, nobody expects me to wear anything “nice” (guess living in your mother’s basement has its advantages).

    Now wifey. Like you, she works in a law office. She very much wants to put some purple or blue or some such color in her hair. The bosses won’t let her. Luckily her tattoos are hidden with a business type of outfit. Unlike a coworker how has to wear a sweater all the time to cover her arm that has been sleeved.

    Maybe it’s the Floriduh lifestyle, but jeans and nerdy t-shirts have been our way of life forever. If we’re going someplace that a t-shirt isn’t quite right (and why would I even go there?), then it’s a nice loud and ugly Hawaiian type shirt for me.

    So, all that to say, wear what makes you comfortable. Let ’em stare. Be your beautiful self!


    Liked by 1 person

    1. I’m actually pretty lucky that the company I work for is very accepting. Half of the people in the office are under 40 and they realized that they needed to get with the times. I don’t have to cover my tattoos up and piercings/funky hair is acceptable, within reason. Still, I always struggle because the office environment and look is SO not me. I always feel like I’m trying to dress like an old lady when I’m trying to be “professional.” I’m sure there are lots of people out there like wifey and myself.

      You know, I never had to wear an army uniform, but I wore one all through middle school and high school and even in culinary school. I actually liked wearing a uniform because I never had to figure out what I was going to wear. Now I am realizing that maybe this is the reason I don’t know how to dress myself. HA!

      Liked by 1 person

  2. Ah the shopping drama! I am now approaching forty (eek!) and all of the clothes from high school no longer fit. I have changed shape and it is weird. I never had a real butt or boobs before and I don’t really know what to do with them. On top of that I look 20 according to everyone so I don’t know what to wear either. I want to wear jeans or yoga pants all the time. I want purple hair and punk clothing. And yet I am in transistion mode with no idea of the next step. So I feel ya. I hope clothes shopping is quick and as painless as possible. Arrr!
    x The Captain

    PS The ma is turning 60 this year and is having clothing and shape issues. At least she loves to shop!

    Liked by 1 person

    1. I survived clothes shopping, mostly unscathed. I only found a few things, but I guess it’s a start.

      I wish I loved to shop. Tell your ma to come here and go shopping with me! Haha. Most of the other ladies in my life also hate shopping, so I don’t even have anyone who can come along and help me out.

      Liked by 2 people

      1. She totally would help ye shop even if ye were a stranger. She loves shopping and being useful.
        Whenever I get complimented on me clothing I laugh because it is almost always a gift from either me mum or aunt. I dress like a bum. Several new things is a good start.
        x The Captain

        Liked by 1 person

  3. I love this post! I’ll throw in my two cents since I’m way older than you and I can put things into perspective. I personally have never “dressed my age” and I never will. I’m lucky to work in a casual office setting where I can wear jeans to work. My “life uniform” as I’ve come to call it is jeans, a hoodie and a graphic T with bare feet (at home) or flip flops (going out). Honestly now that I think about it, that’s sort of what everyone wears in Southern California! I say wear whatever makes you happy and comfortable😁

    Liked by 1 person

  4. Oh, you do make me chuckle, Kiersten 😉
    I’ve never been a follower of fashion, so the wtf do I wear hasn’t really been a problem, however, the big 5-0 is looming ominously on the horizon and I worry the BOHO look I love so much is going to fight against my changing shape – lots of layers does not look as good when you have lots of layers of fat! Lol!
    I don’t really shop on the high street much any more. I’ve found a couple of online retailers that suit my current style and flatter my ever expanding shape. No doubt I will have to look again imminently…
    Buy what you feel comfortable in and enjoying wearing what helps you to lift your head up high, push out your chest and walk with confidence!

    Liked by 1 person

    1. I’m slowly getting there. I bought a couple of new things recently that fit me better and I’m trying to just embrace my nerdy-chic fashion sense more. It’s still tough to go shopping though, considering I hate pretty much everything! Hehe.

      I love the whole online shopping thing. The only downside is not being able to try stuff on first.

      Liked by 1 person

      1. Not being able to try stuff on is a downside. Make sure that the retailer you choose does free returns! I learned the hard way to check that first before placing an order or even looking at their stuff. Lol! It can work out quite expensive to send clothes back.


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