Chicago Business Dinner Outfit: One Jacket. Two Looks.

One of my favorite business travel strategies has nothing to do with packing more.

It’s packing pieces that can do more.

For this Chicago work trip, the denim jacket I wore through the airport became the jacket I wore to dinner the very next evening. One piece. Two completely different looks. One less layer taking up valuable space in my suitcase.

That’s the kind of versatility I look for every time I travel.

The Liverpool denim jacket made its first appearance in my RDU → ORD Airport Outfit, where I chose to wear it on the plane instead of packing it. While I typically travel in one of my lightweight travel blazers, I knew this jacket would be the perfect finishing layer for dinner, making it worth the suitcase space it didn’t take up.

For dinner, I paired it with a lightweight Allegra K chiffon dress, my Sam Edelman Hazel pumps, and my Brahmin Daisy wristlet.

The chiffon dress was perfect for a warm summer evening in Chicago, while the denim jacket added just enough warmth once we settled into the air-conditioned restaurant. Together, they created a look that felt polished enough for a business dinner without feeling overly formal.

The same goes for my Sam Edelman Hazel pumps. They’ve become one of the hardest-working pairs of shoes in my closet, accompanying me to conferences, presentations, client meetings, and business dinners because they instantly elevate an outfit while remaining comfortable enough to wear all evening. When a pair of shoes works this well across so many occasions, it earns a permanent place in my travel wardrobe.

Another travel staple is my Brahmin Daisy wristlet. I own several colors because they’re exactly the kind of low-maintenance accessory I reach for on business trips. The compact size slips easily into my TUMI tote or suitcase without taking up valuable space, but it’s polished enough to carry on its own for dinner or an evening event. It’s one of those pieces that quietly makes travel easier without demanding attention.

That idea—choosing pieces that work harder instead of packing more—is something you’ll see throughout Looks More Expensive.

I don’t build a wardrobe around individual outfits.

I build it around versatile pieces that can move effortlessly from airports to conference rooms, business dinners, and weekends away. Every item has to earn its place by proving it can do more than one job.

This outfit is a perfect example. The same jacket that kept me comfortable while traveling became the finishing layer for dinner the next evening. The pumps continue to work trip after trip. The wristlet packs effortlessly without sacrificing style.

Less to pack.

More ways to wear it.

That’s the kind of closet I’m always trying to build. -LME

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