How to Style a Matching Pinstripe Set: 5 Ways to Wear This Upcycled Power Suit

Business Casual Got Bored. We Fixed It.

Pinstripes usually say office.

This set says I might have a meeting at 3 and disappear with the band at 8.

This one-of-a-kind matching set takes classic dark pinstripes and completely flips the mood with a cropped button-up top and matching pants featuring bold orange side stripes.

It's tailored.

It's sporty.

It's weird in exactly the right way.

And because it's a matching set, you basically get three outfits in one: wear the pieces together or break them apart.

Here's how we'd style it.

1. Wear the Full Set + Cowboy Boots

Don't overthink it.

Wear the matching top and pants together, add black cowboy boots, chunky silver jewelry, and a funky bag.

The pinstripes keep things polished while the orange stripe gives the outfit just enough chaos.

The vibe: corporate cowgirl who absolutely does not work in corporate.


2. Add a Graphic Tee

Wear the cropped button-up open over a vintage graphic tee or fitted tank.

Add sneakers or boots and let the orange side stripes do their thing.

This makes the set feel more relaxed and works perfectly for:

  • Vintage shopping
  • Art walks
  • Coffee dates
  • Markets
  • Casual concerts

Find more pieces to layer underneath in The Modern Alien New Arrivals.


3. Style the Pants Separately

These pants don't need their matching top to be interesting.

Pair them with a black crop top, fitted white tee, oversized graphic shirt, or even a western button-up.

Because of the bright orange stripe, you can also repeat orange somewhere else with your shoes, bag, sunglasses, or jewelry.

Or don't.

Matching is optional around here.


4. Style the Cropped Top With Denim

Take the pinstripe top and pair it with:

  • High-waisted flare jeans
  • A denim maxi skirt
  • Distressed shorts
  • Cowboy boots
  • Statement jewelry

Suddenly the tailored top feels completely different.

This is also why matching sets are secretly wardrobe gold—you aren't buying one outfit. You're getting pieces that can completely change depending on what you pair them with.


5. Take It Out at Night

This set could easily become a killer dinner, concert, or girls' night outfit.

Wear it buttoned with a bralette or fitted tank underneath, then add platform boots, silver jewelry, and a tiny statement bag.

Throw on a leather jacket if it's chilly.

Polished enough for dinner. Weird enough for afterward.

Perfect.


Why Matching Sets Make Getting Dressed So Easy

The hardest part of getting dressed is usually figuring out what goes together.

Matching sets already handled that problem for you.

Wear both pieces when you want an instant outfit.

Separate them when you want something completely different.

And when the set itself is one of a kind and upcycled, you get the ease of a matching outfit without looking like everybody else.

That's our kind of shortcut.


Your Closet Doesn't Need Another Boring Outfit

The best clothes give you options.

Wear this set western.

Wear it sporty.

Wear it edgy.

Break it apart.

Layer it.

Throw cowboy boots underneath it for absolutely no logical reason.

That's personal style.

🛸 Shop New Arrivals at The Modern Alien

Shop The Modern Alien

One-of-a-kind means exactly that.

Once it's gone, it's gone.



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