The Ultimate Guide to Planning Holiday Swag
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The Ultimate Guide to Planning Holiday Swag
Sending holiday swag isn’t just about checking a box. It’s about recognition. Connection. Ending the year with intention…and a little surprise and delight.
And in a world of Zoom calls and global teams, those thoughtful touches go a long way. Whether it’s a hoodie that actually gets worn or a curated snack box that hits on a Friday afternoon, swag is a way to show people they matter.
But here’s the problem: most teams wait too long. They scramble. They settle. They burn budget on gifts no one remembers.
That’s why we made this guide. It’s your step-by-step playbook for getting ahead of the holiday chaos — so your gifts land on time, on brand, and with actual impact.
Step 1: Start With a Goal (Not a Gift)
It’s easy to jump straight to picking products. But before you do, take a step back. What’s the point of your holiday swag?
Because if you don’t know why you’re gifting, you’re likely to waste time, and budget, on swag that doesn’t move the needle.
Start by asking two questions:
Who are we gifting?
Your audience will shape everything from tone to product. Are you sending something to full-time employees who’ve been grinding all year? Longtime clients you want to keep close heading into Q1? New contractors you’d like to bring further into the fold?
What do we want this to do?
Holiday swag can do more than spark joy. Done right, it builds loyalty, strengthens relationships, and keeps your brand top-of-mind without feeling like marketing.
Let’s turn that into real-world goals:
Scenario 1: Remote Employee Morale
“We want our remote team to feel appreciated and connected, especially since they won’t be part of the in-office holiday party.”
This is about recognition, inclusion, and creating a shared experience, even across time zones. Your swag strategy here might lean into cozy items (hoodies, blankets), a hand-signed card from leadership, or a QR code linking to a thank-you video. Something that reminds them: you’re part of this, too.
Scenario 2: Client Retention & Relationship-Building
“We want our top clients to feel valued — and to remember us when they start reviewing budgets in January.”
This isn’t the time for generic promo items. Think premium, gift-worthy, and brand-aligned. A sleek tech gadget or gourmet snack set with a short, thoughtful message can go further than any holiday email blast. It's about staying present without pushing a pitch.
Scenario 3: Internal Culture & Celebration
“Our team’s been through a lot this year. We want the holiday gift to feel like a real reward…not just another branded water bottle.”
If you’re trying to boost morale or celebrate a big milestone, consider a themed box with fun, high-quality items. Maybe a “Holiday Cheers” kit with cocktail tumblers and snacks, or a “Warm & Cozy” pack with candles and fuzzy socks. It should feel more like a gift than a gesture.
Starting with the why makes it easier to pick the right what. It also ensures your holiday swag isn’t just another box on the doorstep — it’s a box that lands with meaning.
Step 2: Budget and Timeline (The Stress-Saving Section)
Need some suggestions? Download our 2025 Holiday Catalog and get started!
No one likes a gifting fire drill. Start with the logistics now, and future you will thank you.
Break your budget into four parts:
- Product cost
- Custom branding (embroidery, print, etc.)
- Packaging
- Shipping (domestic and international)
Work backwards from your delivery date
Here’s a sample production timeline if you want gifts in hands by early December:
Planning + Request Mockups | Mid-July
Final Selections + Payment | Early August
Production Window | 2–3 weeks
Assembly & Fulfillment | 1 week
Ship Date | Mid - December
Pro Tip: Holiday Promo
Order your holiday swag by August 15th to unlock our Holiday Promo:
- 10% off your swag order
- Pre-pay and get 10% back in shipping credits
- Free bonus swag gift
- Free warehousing for up to 6 months
Step 3: Choose Swag People Actually Want
This is where good intentions often go sideways. The key isn’t quantity…it’s relevance. Think comfort, quality, and thoughtfulness over brand-slap giveaways.
➤ For Employees
Skip the notebooks. Lean into stuff they’ll reach for during actual time off.
- Cozy classics: fleece hoodies, sherpa throws, knit beanies
- Wellness: soy candles, bath kits, blue light glasses
- Seasonal fun: hot cocoa kits, patterned socks, travel games
➤ For Clients or VIPs
High-touch, high-impact.
- Premium picks: Ember mugs, Bluetooth speakers, luxe journals
- Quality wearables: Patagonia outerwear, branded golf balls
- Snackable moments: gourmet food kits, charcuterie boards (Domestic only. Unfortunately, no international food shipping!)
➤ Curated Themes
Let the concept lead the pack.
Warm & Cozy
Think fireplace vibes: blankets, tea kits, winter-ready wearables.
Holiday Cheers
For the extroverts: cocktail kits, wine tumblers, sweet treats.
The Frequent Flyer
Portable, TSA-friendly gifts for your always-on-the-go team.
👉 Want more ideas? Download the Holiday Catalog or Browse the Holiday Collection
Step 4: Design It Right (Yes, the Branding Matters)
Swag can be branded and beautiful. It just takes a little finesse.
Imprint Options:
- Embroidery: Best for apparel and beanies
- Screen printing: Bold and flexible
- Laser etching: Sleek for metal and glassware
- Embossing: Premium raised texture for apparel
See our top 3 favorite premium imprint methods to elevate your swag.
Smart Branding Tips:
- Keep logos subtle on wearables. Smaller hits tend to get more use
- Use your brand colors in creative, holiday-neutral ways
- Avoid religious-specific designs to keep things inclusive
Level it up with:
- Custom notes: Handwritten inserts go a long way
- Box messaging: Branded mailers = more visibility
- Tissue paper: Yes, you can print on it. Yes, it matters.
Step 5: Nail the Unboxing
People will judge a box by its cover.
Make the first moment count with thoughtful details:
- Die-cut trays that hold everything perfectly
- Branded tissue or tape for that custom feel
- Personalized messages that show someone put in the effort
- QR codes to team videos or a holiday playlist
- Bonus idea: a mini scavenger hunt on the box itself!
Good packaging elevates perception — without inflating your cost.
Step 6: Ship It (Without the Headache)
You’ve done the hard part. Now it’s just about getting it where it needs to go.
Options:
- Ship in bulk to your HQ or event space
- Send to individual home addresses
- Global shipping available (just check customs if food is involved)
The SwagUp Shortcut: Redeem Pages
Send a link → they enter their shipping info → we do the rest.
You can:
- Collect addresses
- Or auto-ship gifts directly
