Easy Ways to Dress Up Your Casual Wardrobe for a Work Trip

If you work remotely, chances are your daily wardrobe leans toward casual and comfortable. But when a business trip pops up, shifting to business casual can feel like a challenge, especially when you want to pack light. The good news? You don’t need to overhaul your wardrobe. With a few key styling tricks, you can easily dress up your casual outfits for a professional setting while packing light and fitting everything into a carry-on. Here are easy ways to dress up your casual wardrobe for a work trip.

What Does Business Casual Really Mean?

Business casual is the balance between traditional office wear and everyday casual. It’s polished but relaxed—put together without being overly formal. For women, this often includes:

  • Blouses or structured tops
  • Tailored pants, midi skirts, maxi dresses, or dark-wash jeans
  • Blazers or cardigans
  • Comfortable yet stylish shoes

The goal is to look professional while still feeling comfortable. And, of course, every company will have its definition of what business casual is in their organization.

Packing Smart: Fitting Everything into a Carry-On

Packing efficiently will save you time and stress. I’m a chronic over-packer, but I finally have it dialed down and can fit everything into my carry-on suitcase. Here’s how to do it:

  1. Stick to a neutral color palette to create multiple outfits with fewer pieces.
  2. Choose versatile staples – A blazer elevates any outfit, and a simple dress can go from meetings to dinner with a quick shoe change.
  3. Use the 3-2-1 Rule – Pack three tops, two bottoms, and one layering piece to maximize outfit combinations.
  4. Wear your bulkiest items – If you’re bringing boots, sneakers, a blazer, or a heavy cardigan, wear them on the plane to save space.
  5. Opt for wrinkle-resistant fabrics that don’t require ironing. I love pieces from Clara Sunwoo (PINK for 10% off).

How to Dress Up Jeans for a Business Trip

If you’re used to wearing jeans every day while working remotely, you can still wear them on a business trip. Here’s how to make denim look polished:

  • Choose the right fit – Dark-wash or black jeans with a slim, straight, or bootcut fit look the most professional. Avoid distressed styles.
  • Pair with an elevated top – Opt for a silky blouse, structured sweater, or tailored button-down.
  • Add a blazer, cardigan or jacket – This instantly makes jeans look more business-appropriate.
  • Wear polished shoes – Loafers, ballet flats, and booties all elevate denim effortlessly.
  • Accessorize thoughtfully – A structured handbag and simple jewelry complete the look.
Easy Ways to Dress Up Your Casual Wardrobe for a Work Trip
Easy Ways to Dress Up Your Casual Wardrobe for a Work Trip

What to Wear on the Plane

Dressing comfortably for travel doesn’t mean looking sloppy. I wear my Spanx Air Essentials set on long flights. When I flew to Nashville recently, I knew I was going straight from the airport to dinner and wore the 1/2 Zip with my slouchy jeans and block-heeled sock booties.

comfortable and chic travel outfit for women

Dress Up Your Casual Wardrobe: Outfit Formula

When in doubt, follow this easy outfit formula for a business trip:

Base layer: A fitted top or blouse
Bottoms: Tailored pants, a midi skirt, dark-wash jeans, or a maxi dress
Layering piece: Blazer, cardigan, or jacket
Shoes: Loafers, boots, or ballet flats
Accessories: A professional tote bag, dainty jewelry, and a belt

Easy Ways to Dress Up Your Casual Wardrobe for a Work Trip
Easy Ways to Dress Up Your Casual Wardrobe for a Work Trip

I hope these tips will help you to dress up your casual wardrobe for your next work trip! What’s your biggest struggle when dressing for a business trip? Let’s chat in the comments!

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Other posts you might like:

Five Casual Outfits with Blazers

What’s in My Travel Tote

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Business casual outfit ideas

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12 responses

  1. Kellyann

    Jill, this is such a great post! I love the 3-2-1 packing rule and all of your tips are so useful. Being able to fit everything into a carry on is such a great idea and looking stylish while doing so is the icing on the cake!
    xo,
    Kellyann

  2. I love every single look here! These are fabulous tips on packing lighter for business. Thanks for the link up!

    https://www.kathrineeldridge.com

  3. This is such great advice, Jill! I love your business casual looks here, especially that gorgeous blue dress with the blazer, and all of your packing tips too. I need to remember the 3-2-1 rule!!

    Make Life Marvelous

  4. Mireille

    I had not heard of the 3-2-1 rule for packing but I really think it's a great tip!
    http://www.chezmireillefashiontravelmom.com

  5. Living on Cloud Nine

    That packing rule is spot on and very helpful. You do such a good job and always pick the best pieces for the function. I’d say you’ve got the tool to slay outfits for all your upcoming work trips. Fun and makes packing so much better this way.

  6. I like that packing rule, it makes traveling a lot easier. Here, in the Netherlands, a office outfit is way too casual in my opinion

  7. It has been years since I've been on a work trip, but those are good packing tips for travel in general. I also love your outfit with the striped cardigan; it's really cute! Anyway! Thank you so much for sharing, and have a great day, Jill! XO

  8. These are some great packing tips; even though I never travel for work I do often want to have dressier options for dinner or a nice night out.

  9. I've never heard the 3-2-1 rule before, but that's genius! My travel hack is a knit blazer for the plane—it looks very polished but it's super comfy, like a sweater!
    Cheryl Shops | http://www.cherylshops.net

  10. I didn't know about the 3-2-1 rule before but it makes so much sense!

  11. I didn't know the 3-2-1 rule either. Makes putting together outfits and packing lots easier. My daughter works from home but has occasional business trips. This post will be a help to her!