Why Classic Style Doesn’t Have To Be Boring

Classic Style Outfits

I recently talked about the case for the simple outfit. I think a lot of people overthink a simple outfit, and therefore think their style is boring. That’s why I think a lot of people stray away from those classic pieces because they’re afraid they’re BOOOOOOOORING. And I’m here to tell you (respectfully) YOU’RE WRONG. There’s so many ways to interpret good classic style outfits and make them your own!

Think about it this way – every outfit you put on isn’t going to be amazing. Let those special purchases shine – we don’t need to see them all at once. I firmly believe a good wardrobe has more of those every day items in ADDITION to the special ones. But what makes a great outfit? When those special pieces fit seamlessly into your classic style. THAT’S the kind of personal style I really strive for.

The five pieces in this post are still the basis of what I revolve my (fall) classic wardrobe around.

Classic Style Outfits

I came to the realization over the years that I usually had a closet full of clothes but nothing to wear. Now when I look at my wardrobe, I know I’m going to be able to find something to wear. Whether it’s an outfit I’ve worn a million times or pieces I’m mixing and matching (i.e. new with old), I really never have to worry about being late just because I can’t pick out something to wear.

When I think about classic style outfit ideas, I don’t necessarily think of “oh clothes that never go out of style”. While that’s PART of it, I mostly see classic style as dressing in a put-together way. I think there’s a difference between timeless pieces and classic style. But they do go hand in hand.

How I think about classic style outfits:

  • Neutral colors as a base (easier to add a pop of color)
  • Traditional prints and stripes
  • Simple silhouettes and tailored pieces

When it comes to “mastering” classic style outfits, don’t think that the word “investing” means spending $1,000 on a cashmere sweater. You just need to be investing in a piece that’s well made, fits well, and has longevity in terms of wearability. Once you invest in these kinds of pieces, coming up with classic style outfits will be much easier.

The outfit I’m wearing in this post is filled with easy pieces that I can wear SO many different ways and with SO many other things in my closet. A button down so oversized that it feels like you took it right from your dad’s closet? CLASSIC. Leopard ballet flats? ALSO CLASSIC. And a red cashmere sweater? DON’T EVEN GET ME STARTED.

THAT’S my definition of classic style. And I don’t think it’s boring, right?

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  1. 10.31.23

    wow, amazing blog. keep sharing the good work.

  2. 12.27.23

    I never go without my eco-bottles no matter what outfit I’m wearing. I have one that always accompanies me even in a classic outfit.

  3. 2.26.24

    Simple is good. It’s sometimes harder for me to dress simple because i don’t have the nack to put simple pieces together. This article inspired me to try the more simple look. :),