What Does It Mean to Be “Well Dressed”? (and why does it matter?)

One of my biggest areas of interest is history and historical fashion. I’ve always loved learning about history, especially what people did day to day: what they ate, what they wore. I especially love looking at old photographs and seeing how people dressed and did their hair.

My grandmother was always a smart dresser. She lived in a time when no matter whether it was a special occasion or you spent the day at home, everyone still presented themselves beautifully. I’m not saying the 50’s were a better time or that we should go back to it (au contraire!), but there’s one page we can take from the history books: the art of presenting ourselves beautifully every day.

My grandmother’s life wasn’t perfect, but one thing was certain: she was always well dressed. Her hair was done and she wore her signature lipstick. I fondly remember her bold red lip when she took me shopping at the commissary with her when I was little.

These days seeing someone who is put together and well dressed is more of a rarity. People tend to only dress well for special occasions anymore (and I’ve heard some horror stories of people who don’t dress appropriately even then).

There seems to have been an attitude shift towards dressing well in recent years. It’s become so common to see people in ratty exercise clothes or even pajamas in public that dressing nicely is starting to get looked down on. If you decide you want to wear a nice dress one day, you may get snarky comments from other people asking, “Where are you going, dressed like that?” or saying, “Someone sure is dressed up today!” sarcastically. It’s enough to make one not want to bother.

It can be difficult to want to put any effort into your appearance when you’re at home all day with the baby who spits up after every meal, or when you’re carting the kids to the grocery store. Why bother when you’re going to be spat up on/spilled on/grabbed with sticky hands?

So let’s talk about dressing well and why it’s actually important.

What does it mean to be “well dressed”? 

Dressing well is:

• Putting thought into what you wear. Instead of carelessly selecting semi-dirty exercise pants lying in a heap on the floor, you intentionally pull out a nice pair of clean pants.
• For your clothing to be well cared for. No rips, holes, or stains. Clothes are in good condition and pressed if needed.
• Clothing fits well. Even if you can’t take it to the tailor, it should not be way too big; conversely, don’t squeeze into pants that are two sizes too small.
• Being appropriately dressed for the situation. A sundress is great for a summer brunch or backyard BBQ, not so great at a funeral.

What dressing well is not:

• Spending a ton of money. You don’t have to spend a fortune on designer clothing to be well dressed. You can look presentable on any budget. It’s about putting thought and effort into your look, not about how expensive the individual pieces are.
• Dressing inappropriately for the cultural and geographical context. Be mindful of where you are, and try to dress respectfully. If you’re in Paris visiting the Louvre, you may want to rethink those leggings and sneakers.
• Being uncomfortable. You don’t need to wear heels, clothes that make you too hot/cold, or clothes that pinch and squeeze to look nice. (Unless we’re talking about very specific situations with certain dress codes, but I’m talking more about general day to day dressing.) You can wear clothes that are comfortable AND nice looking and be well dressed.
• Looking perfect. Real life isn’t an Instagram feed or a Pinterest board. We all have days that are better than others. You don’t need to have perfectly applied makeup and be dressed to the nines. You can still dress well in a nice looking dress or shirt and pants that are comfortable but also look good on you even if it’s one of those days.

Why does being well dressed even matter?

Because it’s about living our best lives. We have one life to live. What’s the point of having beautiful clothes in our wardrobes if we never wear them? We should enjoy the clothes we have rather than saving them for a special occasion that may not come.

It’s about making yourself feel good. If I’m having a rough day, I find that dressing well boosts my confidence and makes me feel better. Wearing something unflattering when I’m already not in the mood just makes me feel worse. It’s extra nice when I get a compliment on what I’m wearing – it really brightens my day! (And I always try to compliment my friends on what they’re wearing if they look good. You never know, you may really brighten their day.)

It’s about making every day a special occasion. Celebrate the new day by dressing presentably. Enjoy the beginning of your day by intentionally putting on something you like that you look nice in.

It’s about showing pride in ourselves and our appearance. I feel better about myself when I’m dressed better. I want my children to remember their mother taking pride in her appearance. It’s not vain – it’s showing my family that they matter by dressing well around them, even if we’re just at home.

It’s about showing respect to others. Dressing well and appropriately is a sign of respect. If I showed up dressed inappropriately for a wedding, it would be a sign of disrespect to the bride and groom. If I dress nicely for a nice dinner out, I’m showing everyone around me there that I respect them making this evening a special occasion for me.

I would love to know your opinion on dressing well. What does being well dressed mean to you? Do you want to try to dress better, or are you one of the “you can pry my leggings out of my cold dead hands!” types? Please leave me a comment below, and let me know if you want more in depth posts about this.