Have We Forgotten How to Dress Up?

Why Comfort Has Taken Over.

*Personal photo

The other day, I went to an art gallery for a guided tour on Impressionism. At first, I was taking notes and photos of the paintings, but as the excursion neared its end (and so did my attention span), my eyes started wandering—and they landed on what people were wearing.

When you read fashion blogs, you might come across ideas like “city walk outfit,” “first date outfit,” etc. Now close your eyes and picture yourself a perfect “museum visit” outfit. What would you wear? What do you imagine others around you wearing? What would make you feel inspired and aligned with the activity? If you are like me, you too would be surprised by the striking difference between expectations and reality.

I noticed that people tend to dress down. This is not by any means a surprise for me since DC fashion is extremely casual and conservative regardless of lifestyle. But I still find museums and theaters somewhat sacred places.

Comfort vs Style

*Tibi CP scale

Some of the outfits people wore seemed to say, "I'm on a hike/nature walk/other sport-related activities." I’m not saying this to criticize anyone’s clothing choices, nor is this a “how you should dress instead” piece. I honestly don’t care unless it’s a request from my clients to work on their wardrobe and style. But once I started observing what people were wearing, I couldn’t stop thinking about the idea of dressing up.

It seems that overall comfort has won over style. Don’t you think so?

Maybe it’s because my own lifestyle has become more casual (I rarely go out), and I don’t see people dressing up much anymore. But even when I do head out for a stroll in the city, I mostly see ultra-casual, sporty outfits. To me, visiting a museum is one of those occasions you can dress up for. And when I say "dress up," I don’t mean anything like night-out or special occasion attire. It’s more about elevating your everyday look just a little. Why isn’t there more space in our routine for being a bit more dressed up? Or is there? Is this a DC thing, or have you also noticed a trend towards more casual dressing in your city? Tell me, I’m very curious.

Creatures of Habit

I’ve spent a fair amount of time traveling around Europe, and this isn’t the scene you’d typically see there. The overall aesthetic is less monolithic—more creative, daring, and vibrant. In the U.S., there’s an increasing emphasis on comfort over what might be considered “impractical” or fancy. In London, for example, it’s not uncommon to see someone dressed to the nines just for an afternoon tea. Here in DC, it’s more common to see casual athleisure even in a setting like a dinner at a restaurant or a theater. How much do our surroundings shape the way we dress? Quite a lot, that’s what I think.

For me, it’s a delicate balance. When I lean too far into practicality and neglect creativity, I don’t feel great. It doesn’t empower me. On the other hand, if I overdo the creative side, I risk standing out too much, especially in a place like DC.

At first, I thought everybody is comfortable with this “casual status quo.” However, in my work with clients, I often hear from them that they’re tired of looking too basic and relying on the comfort of leisurewear. Even when they have beautiful pieces in their wardrobes, the habit of reaching for the same items over and over again can be hard to break. I have a few thoughts on why this happens.

Decision Fatigue

*Pinterest

Everyone’s familiar with the term "decision fatigue" these days. Too many options, too many tasks, too many small decisions to make. Our wardrobes are overflowing—shelves packed, hangers overloaded, closets bursting. We buy more and more for that fast dopamine hit, but the result is the opposite of what we expect. Instead of a dream wardrobe, we get clutter that prevents us from wearing even 50% of what we own (it’s more like 20%, at best). Our brains protect us from dealing with another decision by guiding us to reach for the same things repeatedly. Usually, it’s something basic that lets us blend in and avoid standing out.

The Crowd Power Factor

*Personal photo

“I don’t want to stand out too much—everyone around me is so casual,” I often hear from my clients. Yet, in the next breath, they say, “I want to feel like myself and feel more put-together in my clothes.” There’s a constant struggle between blending in and allowing yourself to do what feels right for you. The power of the crowd and what others wear around us often wins.
There’s another layer to standing out, too—attention. People look at things that stand out. Not everyone likes that attention, and not everyone knows how to interpret it. Are they looking because something’s wrong with the outfit, or because they like it? Many people tend to think negatively, especially if they’re not completely confident in their choices.

Have you ever felt like blending in wasn’t quite enough, but standing out felt uncomfortable?

I’ve developed a few strategies to help with these concerns:

• By learning more about yourself—what suits you and what you love—you’ll feel more confident in your outfits and be less concerned with others' opinions or attention. You’ll know what you like, and the rest won’t matter.

• When I introduce new outfits to clients, and I see their excitement mixed with fear of standing out, I offer this advice: Wear the outfit to a place where you’re unlikely to run into anyone you know. Get comfortable in it. Once your brain has adjusted, wear it to the office or out with friends. You’ll feel less self-conscious since you’ve already made it part of your comfort zone.

In my work as a stylist, I focus a lot on marrying comfort and style. I think you should never deprive yourself of the pleasure of dressing up even slightly regardless of what people around you might wear. Indulge yourself in this styling pleasure, put in extra effort, catch yourself every time you grab the same athleisurewear, and maybe go for something more elevated. Let you be you.