Clothes piled on the bed, shoes kicked across the floor, already late for the event, and still you feel: I DON’T KNOW WHAT TO WEAR! Relatable? This is a very common issue. Uncertainty about what to wear on different occasions leads directly to accumulating more clothes, which only makes the situation more complicated next time. Let’s get into what we’re signaling with our wardrobes, and how we can feel more confident in our choices.
We’re most likely to get spun up about what to wear when we’re going to meet unfamiliar people, in an unfamiliar setting, and perhaps at an unfamiliar type of event. Why, though? If these are people we aren’t going to see often, a place we might never visit again, or a type of event we don’t usually attend, then why would it matter? We allow ourselves to fret about WHAT THEY’LL THINK (whoever ‘they’ are) because only after the event is over will we know how we fit in.
I once attended an evening wedding in New York. It had ice sculptures. I dressed up, making my best effort in a floral-print linen sundress with sandals. As soon as I walked in, I understood that I’d gotten it wrong, because the other women were in evening looks with satin dresses and heels. I had no idea what a blowout was, nor was I wearing makeup. What happened? I shared a table with my date and a nice couple who kept us laughing all night. The bride and groom are still my close friends, and we’ve been on vacation together a couple times. (In fact even my date has been out to visit, because we’re still in touch). As far as I know, I never saw any of the other guests again.
I walked away with a pretty clear image of how to dress for a formal evening occasion. I knew right away that I could have picked up an appropriate dress at Goodwill for $15, and nobody would have known. In fact, I can repeat a special-occasion outfit at multiple events, because my husband doesn’t care and nobody else will notice.
The longer we take to get ready, the less satisfied we are with our appearance. That’s what research says, anyway. It makes sense to me. It takes me about ten minutes to “get ready” and leave the house, half an hour if I’m doing the full Las-Vegas-nights routine. If someone doesn’t like how I look, then great! Someone that shallow and superficial will stay clear of me, leaving me free to have interesting conversations with people who have their priorities straight. People value my company for my sense of humor, storytelling, and ability to be a good listener. None of those qualities has anything to do with physical appearance. On the contrary. If I looked too polished, maybe nobody would believe I could be a good listener or a funny storyteller.
What are we signaling with our clothing choices?
Friendly / aloof?
Relaxed / fussy?
Competent / wacky?
Professional / casual?
Married / single?
Stressed / happy?
It seems like one of the strongest style statements that many people make with their casual wardrobe is what type of music they’re into. Rocker, country, punk, skater, raver, goth, and I’m sure many others I’m too tragically unhip to recognize. We know who we are when we put on casual clothes. We’re only wearing the stuff we trust to fit and be comfortable. We’re signaling a bit about ourselves, enough that someone who’s into the same style might approach us and strike up a conversation. That’s how I met a guy at the cafe who was willing to answer a few questions about jiu jitsu for me - his t-shirt advertised it. Maybe it doesn’t matter at all what you wear on casual days; I’ve seen people out in public wearing everything from pajamas to bikinis to, a couple times, nothing at all.
We feel more out of our depth when we’ve been invited to a wedding, party, or job interview, am I right?
This is what people do to make their clothing choices more difficult.
Keep everything, even when it doesn’t fit
Keep everything, even though it NEVER fit and the tags are still on it
Keep everything, no matter how old it is
Keep everything, even if it’s stained or full of holes and the unworn clothes aren’t
Keep everything, even if it’s scratchy or uncomfortable
Keep everything, even if it doesn’t go with a single other item and there’s no way to wear it
Keep shoes that cause blisters and actual bleeding
Buy things because of their price, not how they fit or how they look
Buy things out of obligation or guilt, not wanting to disappoint the sales clerk
Decide on garments individually, not on how they play into the wardrobe as a whole
Having hundreds of garments in every cut, style, color, and print, and several sizes, can only send inconsistent signals. Wearing clothes that don’t fit, or combining items that are too tight and too loose, doesn’t send a clear signal, except maybe [does not use a full-length mirror]. Limping from impractical shoes, tugging things into place over and over, makes people worry if you’re okay. Showing up late because of one too many head-to-toe outfit changes makes you look, at best, frazzled, and at worst, inconsiderate. All you really need is something clean and a warm smile.
My entire wardrobe fits into two suitcases. This is because I only feel like I need a few changes of clothes for each of my different roles. Casual summer, casual winter. Business casual summer, business casual winter. Workout summer, workout winter. Camping clothes. A few cocktail dresses. Boom, done. When I get tired of something or it gets worn out, I replace it with something else. I had to replace my entire wardrobe when I reached my goal weight, and since I’ve settled into one clothing size, I’ve been able to figure out how a capsule wardrobe works. Every single thing I own:
Works with at least three other items
Can be machine-washed and, mostly, machine-dried
This is why I’m confident when I walk out the door. I’ve made my choices in advance, and I’m wearing things I’ve worn many times. I also choose where I go or don’t go, and it’s very rare that I would feel obligated to go somewhere where I wasn’t sure how I fit in. Mostly, I feel confident enough in my social skills (now) that people are a lot more likely to remember what I said than how I looked.
I’m trying to send a few clear messages with my wardrobe
OMG A GUY JUST LEANED OVER AND TOLD ME: “YOU LOOK GREAT”
(I’m married, and not looking for male attention, but it was funny that it happened while I was writing about clothes and appearance).
I’m trying to send a few clear messages with my wardrobe, namely: Married, friendly, competent, smart, entrepreneurial. There are other signals I can’t do much about, such as: middle-aged, fit, Western, distractible, more eccentric than I wish I were. When I decide whether to buy new clothes, I can ask, Does this send the message I want to send?
I look like myself, just like you probably look like yourself. (Unless you’re trapped in a work uniform). Sooner or later, the people around us will figure out what we’re like. Core personality shines through eventually. We should focus more on what kind of friendship we can offer and what roles we’d like to play in life, and less on WHAT THEY’LL THINK about how we look.
I've been working with chronic disorganization, squalor, and hoarding for over 20 years. I'm also a marathon runner who was diagnosed with fibromyalgia and thyroid disease 17 years ago.
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