If you’ve ever tried to pack for a work trip where the dress code is a little unclear, you know how tricky it can be. Not quite business casual, not quite vacation… just somewhere in the middle. That was exactly the situation for my recent trip to San Diego.

I was there for a few days at a beautiful resort, but I wasn’t on vacation — I was working. I was asked to lead music for an event hosted by the organization I used to work for. The dress code was “resort casual,” with dresses, skirts, or pants and blouses or sweaters suggested. So I wanted to wear outfits that felt polished enough for a work setting, but still relaxed enough to fit the environment.

This is one of those scenarios that can easily lead to overpacking or ending up with outfits that don’t feel quite right once you’re there. I know you know that feeling!

Today I’m sharing what I packed and what I wore in San Diego. If you have a spring work trip coming up, or you’re trying to figure out a casual resort dress code, this will give you some ideas and a good starting place!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.

What Does “Resort Casual” Mean for a Work Trip?

“Resort casual” can feel a little vague, especially when you add a work component into the mix. On one hand, you’re at a resort, so things lean more relaxed and comfortable but still polished. On the other hand, you’re still in a work setting, so you don’t want to look too casual or underdressed.

For this trip, I wanted resort casual work outfits that were:

• polished, but not overly structured or corporate-looking
• comfortable with a laid back element, but still put-together
• a step up from everyday basics and had some work attire mixed in

The dress code suggested dresses, skirts, or pants with blouses or sweaters, which gave a helpful starting point. From there, I focused on pieces that felt easy to wear but still appropriate for being “on” throughout the day.

A few things I kept in mind while planning my outfits:

• No denim – This is fairly common in resort settings, even though I LOVE jeans and think they can look really good. But to be safe, I skipped it and kept everything feeling a little more elevated and work-appropriate.
• Lightweight, breathable fabrics – It was on the warmer side in San Diego the weekend I was there, so I wanted pieces that breathed well but also looked polished.
• Easy, mix-and-match pieces – I wanted to have options in case what I originally planned didn’t work out.
• Shoes that are comfortable but polished – Flats that went with everything, sandals that went with everything for off-duty times, and lifestyle sneakers for traveling.

The goal I aimed for was to bring things that would feel appropriate for a casual office but styled in a slightly more relaxed and fun way that fit the vacation vibes of a resort.

What I Packed for My San Diego Work Trip

When I was packing for this trip, I wanted to make sure everything could mix and match easily, but I also wanted my outfits to be fun. I focused on pieces that were breathable but felt polished. And, I wanted pieces that worked for that in-between “resort casual” dress code — nothing too structured, but nothing too casual either, and definitely comfortable enough for all-day wear.

The Weather Forecast

My trip was at the beginning of March, and the forecast said it’d be in the 70s. But, I was still uncertain of a couple of things.

First, I lived in San Diego for 20 years, so I know the weather can play tricks on you. The forecast can say 68 degrees and be really warm, as you’d expect it to be, or it can feel like it’s freezing, depending on which part of San Diego you’re in and whether it’s the winter or summer months. Also, there can be 20 degree swings from morning to evening, so it may only be 68 for an hour of the day and be much colder the rest of the day.

So, even though the forecast said 70s, I wasn’t sure what temperature we’d really be getting at the beginning of March. Thankfully, I was able to ask my friends and family who still live in San Diego to confirm that it was actually warm. 😆

Second, though, I wondered how cold it’d be in the meeting room. Sometimes hotels can be pretty chilly! I still wanted to bring a layer or two just in case the venue was cool.

Here’s what I packed:

Dresses for Evening Events

I packed two dresses for evening events. I didn’t think I’d need both, but I couldn’t decide on colors and both fit in my suitcase, so I figured why not? Well, I ended up wearing both! Having those options made it really easy to get dressed for those slightly dressier moments without overthinking it.

Shoes That Work with Everything

When it came to shoes, I focused on pairs that would work with multiple outfits. I brought options that could go with everything:

• Flats — for when I wanted something a little more polished.
• Metallic sandals — that would be dressy if I did choose sandals.
• Lifestyle sneakers — for travel days or in case I went for a walk during my stay.
• All worked well with my wide leg pants, dresses, and even my more relaxed outfits. Having just a few pairs that worked across all my outfits made getting dressed so much easier and reduced what I had to pack!

Swimsuit & Sandals for Pool

I also packed a swimsuit and waterproof sandals that I could wear to the both the pool and with other outfits, in case I wanted to go in the hot tub during free time. I could also walk for long periods in these sandals.

If you’re planning a trip and want a full breakdown of the things I always bring with me, I shared all my go-to travel items in this post: 17 Travel Items I’ve Used Forever — for Your Next Trip. It’s a mix of practical essentials that make traveling easier and a few things I never leave home without!

What I Wore in San Diego: Resort Casual Work Trip Outfits

These are the outfits I wore!

Welcome Dinner

This was the time for mingling, networking, and getting acquainted. I relied on my new favorite dress of the season, and it was perfect! This dress is great for baby or bridal showers, graduations, dates, or days you simply want to be a little dressier. It has lots of details that make it look special, nips in at the waist to give you shape, is fully lined, and has pockets! It comes in a TON of great colors — I honestly had a hard time choosing. (You’ll see later in this post!) See all the colors HERE. I’m wearing size S.

I added yellow earrings to pop against the green! Find my earrings HERE. They’re made from leather and are SUPER lightweight and comfortable.

Daytime Work Outfits

Here are the outfits I wore during three days of sessions and events during which I led music.

Being at a resort, I wanted to pull in colorful items — and I loved wearing red with aqua!

This sweater is the relaxed-fit one I’ve been telling you about for the last few weeks. I’ve shown it worn untucked in previous pictures, but it worked nicely in a front tuck here. This sweater is super SOFT and comfortable, and it hits that relaxed-but-polished balance I was going for. Find it HERE. I’m wearing size XS as it runs large. Also, some of these colors are now sold out, so there is an identical one from another seller with more colors HERE.

If you’re looking for a more fitted sweater, I like THIS option too. I wear this one in size S.

I knew these lightweight pants would be perfect for the weather, and the beautiful green is the kind of color I wanted to wear at the resort. I paired them with my go-to lightweight, gauzy top (HERE), which is a summer staple for me. I saved this outfit for one of the warmer days since it is so lightweight, and it worked out great!

I added a little animal print with my earrings to spice up this outfit of all solid colors. Find similar earrings HERE.

My pants are unfortunately no longer available in this color, but a few sizes are still available in other colors, HERE. I’m wearing size 6.

The last day included just a morning session, and after which I’d change into jeans and a t-shirt to travel home. This is what I wore for that last session — the same easy-to-wear trousers I wore in the first outfit, in a different color, and another one of my go-to breathable warm-weather tops. I wanted to bring in some print to change things up a bit.

Special Event Dinner

We had another special event — a dinner cooked by the winner of The Next Food Network Star, Aarti Sequeira, with a live cooking demo. I was wearing the green pants outfit that day, and while I didn’t have to change, I had this dress and figured why not?

This dress is the same one that I wore in green on the first night. Like I said, there are too many great colors to choose from, so I bought two! Green for days I want to stand out and this navy colorway for when I want to keep it a bit more lowkey. Again, I added colorful earrings to make it pop. Find this dress HERE. I’m wearing size S.

Easy Resort Casual Outfit Formulas You Can Copy

If you’re packing for a similar trip, here are a few simple outfit formulas you can use:

• Wide leg trousers + breathable blouse + flats
• Wide leg trousers + relaxed sweater + flats
• Lightweight colored pants + breathable neutral top
• Dress + lightweight jacket + flats or metallic sandals

What I Didn’t Wear (And What I’d Do Differently)

I packed a white cardigan in case the rooms were cold, which I only really wore on the plane. I’d still pack it again if I were on a similar trip, though, because I don’t want to be cold in meeting rooms.

I never wore my metallic sandals, as my tan flats worked for all my outfits.

Also, while there was plenty of free time, I didn’t spend mine on a nice stroll around the resort or at the pool. I just visited my friends and family at their houses or running errands like it was a normal day in my old stomping grounds. That’s to say I didn’t need my swimsuit or waterproof sandals.

I also never wore my sweatshirt, since I didn’t bother to change when I visited friends outside the resort. I also didn’t need it on the plane, as my cardigan was good enough.

I could also have VERY easily traveled in the wide leg trousers and totally skipped bringing jeans and t-shirts. My flight was only 1.5 hours, and my trouser outfits were plenty comfortable. But jeans are my security blanket, so the thought of not having them at all feels weird! 😆

If I wanted to whittle down my suitcase, though, I would have cut my swimsuit and waterproof sneakers, jeans, t-shirt, and metallic sandals. That would leave quite a bit of room!

For Your “Resort Casual” Trip

That’s what I wore to my “resort casual” San Diego trip! If you’re packing for a similar trip, I’d focus on:

• a few versatile bottoms
• breathable tops that can be dressed up or down
• one or two layers
• and shoes that go with everything

I hope this helps give you ideas for what to wear on your trip!