Every September, swag orders start to shift into fall mode. Tees and polos are being replaced by quarter-zips and vests, while bottles are being replaced by insulated mugs.
That timing also makes this list useful for sales kickoff planning, since sales kickoff prep often overlaps with the holiday gifting season. If you’re sourcing for both, the same fall-friendly items can help you narrow down what works for a sales kickoff while you’re already thinking through holiday orders.
That said, here are the swag items that are trending this September, plus where each item fits into a sales kickoff.
What is a sales kickoff, and why do you need swag for it?
A sales kickoff (abbreviated as SKO) is an annual meeting where the sales team looks back at the year that just ended, learns what’s changing, and gets aligned on the goals ahead. Most run for two or three days in January or February, with marketing, operations, and customer success often joining too.
Our full guide to planning a sales kickoff covers the agenda, themes, venue, and everything else that goes into planning one.
Swag is important for any sales kickoff event, and here are a few reasons why:
Swag keeps the sales kickoff going even after the event ends: Even after the event ends, having premium swag apparel or drinkware can make your sales team remember the event, even after months.
Swag is one of the few parts of the event people actually keep: PPAI’s Product Power 2026 study found that 65% of consumers are very likely to keep a branded item like swag for six months or longer when the material and construction hold up. What this means for your swag is that you should opt for high-quality swag items.
Swag gives the awards moment something physical: Names get called from the stage at every kickoff, and handing someone a premium quarter-zip or vest gives the recognition something they can take home and actually use.
How do you tie the swag to your sales kickoff theme?
Before we dive into the trending swag items you should consider for your sales kickoff 2027, first, you should know how you can tie your swag items to the theme of your sales kickoff. Here’s how you can do that:
Color - Use the colors from your theme and apply them across the collection. Keeping the same two or three colors across apparel, drinkware, and bags makes everything feel like part of the same kickoff.
Decoration - Use embroidery on apparel, laser engraving on drinkware, and screen printing on totes. The decoration can change by item, but the logo and theme should stay consistent. Check out our branded apparel guide to see which methods work best for different fabrics.
Swag items related to location - If you’re having your sales kickoff elsewhere (specifically a beach, resort, or mountains), pick items that are related to the location. So, if it’s at a beach, pick drinkware suitable for a warmer climate. Select insulated vests for cooler locations.
From there, the three choices above should work together. Start with the theme, turn it into a color palette, choose decoration that fits that look, then use the location to narrow down the actual products. A mountain-themed kickoff, for example, might mean earth tones, embroidered fleece, and insulated drinkware, while a coastal theme could mean lighter colors, tonal branding, and warm-weather items.
Here’s what that can look like across five common sales kickoff themes.
5 sales kickoff theme examples
Summit, peak, or elevate - This theme works well when the year ahead is ambitious, and you want the kickoff to feel focused on what’s next. Build around outdoor brands, warmer layers, and drinkware. A hat adds some color without taking the theme too literally.
Momentum, acceleration, or next level - This one is a good fit for teams coming off a strong year and trying to keep that energy going. Go for a quarter-zip, tech items, and a backpack so you can give a more streamlined kit. Keep most of the palette neutral and bring in one brighter accent color.
Championship or playoffs - Best when recognition and awards are a big part of your sales kickoff. Team colors make sense here, along with a premium item for an award people can actually use afterward.
One team or built together - Makes sense after a reorg, acquisition, or year where bringing everyone together is part of the message. Keep the main kit the same for everyone and in one color. If you’re also recognizing top performers, give those gifts separately so the kickoff kit still feels shared across the team.
Coastal, horizon, or open road - A natural fit for a kickoff at a warmer destination or one with outdoor activities built into the schedule. Lighter colors and tonal embroidery work well here, and the apparel should be comfortable enough to wear from the morning sessions through dinner or an evening event.
One thing to note is to always have a tote to give away with your sales kickoff swag. It’s easier to give a premium apparel or drinkware inside a tote bag, plus it also gives your sales team an easy way to carry their swag for the rest of the event.
What are the trending swag ideas for sales kickoff 2027?
As mentioned above, start with a tote bag like the Custom 100% Cotton Canvas Tote Bag | 12 oz ($3.79). This isn’t a gift on its own, but rather, it’s an item that you should use for keeping the swag items together for the giveaway. As mentioned, it’s easier to give away and carry around swag if they’re all in a bag already.
With that out of the way, here are the trending swag ideas for sales kickoff 2027.
Quarter-zips and polos
Warm without feeling bulky, with a sweater-like finish that looks a little more polished than standard fleece. This is easy to wear during sessions, at dinner, or on the flight home. A strong pick when everyone is getting the same apparel.
This is a premium pick, so make sure to give it to your top sales performers. Made with stretch microfiber, moisture-wicking fabric, and UPF 50+, with a polished finish that feels worthy of a top-performer award. Peter Millar also has the brand recognition that makes it feel like a real reward.
Mercer+Mettle Soft Spacer 1/4-Zip ($45.98)
A lightweight apparel with enough structure to look polished in photos. The recycled polyester, rayon, and spandex blend also has odor-fighting treatment and UPF 50+. A good option when you need polished apparel for a larger group without pushing the budget too far.
TravisMathew Ocean Villa 1/4-Zip ($135.00)
A soft brushed interior and a cotton, polyester, and elastane blend make this an easy layer for cooler evenings. TravisMathew gives it a more relaxed feel than Peter Millar, which works well for regional awards or mid-tier recognition.
TravisMathew Glenview Solid Polo ($82.50)
This polo is wrinkle-resistant, quick-drying, and made with four-way stretch. A good fit for resort kickoffs where the day can go from sessions to golf or drinks without much time in between. It stays polished without feeling too formal.
Vests
Eddie Bauer Fleece Vest ($55.90)
A warm, lightweight fleece with a zippered chest pocket and front pockets. Made with 100% polyester fleece and Low Impact Technology, which uses less water and energy during production. It’s an easy choice for a general-attendee layer.
Port Authority Core Soft Shell Vest ($40.48)
Wind-resistant, water-repellent, and lined with microfleece. It gives a large group a polished outer layer without pushing the budget too far. A good option when everyone needs to match for the group photo.
Vuori Men's Sunday Insulated Hybrid Vest ($158.00)
Vuori is already a brand people buy for themselves, which makes this one feel more like a real reward. The insulated hybrid design puts it at the premium end, so it's better suited for top performers' recognition.
Drinkware
A 40-ounce capacity, comfortable handle, and double-wall insulation make this a strong choice for a full day of sessions. The straw folds down, and the lid closes securely, so it's easy to carry in a tote between sessions.
Lightweight for its size, with double-wall insulation that keeps drinks cold for up to 10 hours. The carry handle and Fast Flow lid make it easy to take it from the conference room to the airport. Stanley's color options also give you plenty of room to match your kickoff palette.
A built-in flip straw, folding handle, and leakproof design make this one easy to use throughout the day. It also fits in a car cup holder, so there's a good chance it keeps getting used after the kickoff.
The stackable design makes these easier to store when you're ordering hundreds at a time. Double-wall insulation keeps drinks hot or cold throughout the morning. A good YETI option when you want the brand without moving into the higher price range.
Hats, tech, and bag
Richardson Peach Twill Dad Hat ($13.39)
A low-profile six-panel hat with a soft crown and pre-curved bill. The 100% peach twill gives it an easy, everyday feel that works well beyond the kickoff. A good budget pick for large groups.
Richardson Pro Twill Snapback 212 ($12.00)
A structured six-panel snapback with an adjustable closure and Stay-Dri sweatband. With more than 24 colors, it's easy to match almost any kickoff theme. The classic shape also works well for group photos.
A 10,000 mAh power bank with a built-in USB-C cable and Apple Watch charging pad. Perfect for long conference days when everyone's phone battery starts disappearing. It's the kind of swag people can use during the event and long after it.
Fits a 15-inch laptop and has plenty of room for chargers, headphones, and other daily essentials. Recycled polyester, luggage passthrough, and a lifetime warranty make it a strong upgrade from a basic tote. A good option for leadership or top-performer kits.
Prepare Your Sales Kickoff Swag with PerkUp
A sales kickoff happens right after the holidays and has very little room for delays. That means that your swag needs to be planned around the event from the very start. The easiest way to do that is to use a swag management platform like PerkUp, where you have one place to manage your sales kickoff swag, including the production, shipping, tracking, and even reporting that go with it.
For one, PerkUp offers a comprehensive event management dashboard where you can add your sales kickoff event and its venue address. From there, you can see the production timeline, delivery deadline, and shipping status. This allows you to monitor the swag items that have already arrived, what's still in production, and where shipments are headed. You can also catch holidays that fall inside your production window before they throw off your timeline.
If you're having your sales kickoff abroad, PerkUp can also handle that easily and efficiently, thanks to its regional warehousing and supplier network in the US, Canada, Mexico, the UK, Europe, India, China, and Australia, and global delivery to 65+ countries. This means that you won't have to worry about organizing your swag deliveries yourself and handling the customs associated with global swag sends. PerkUp ships delivery duty paid whenever possible and reimburses you in full whenever there are unexpected costs that come up.
Swag flexibility is also one of the core offerings of PerkUp. Aside from event swag and management, the platform also offers bulk swag, On Demand swag, swag kits, swag stores, and 5,000+ gift cards that you can use for more than just your sales kickoff. Add automated milestone gifting and 200+ integrations, and you can also have your swag deliveries automatically sent based on your preset triggers. PerkUp's own design agency can also assist you in preparing your swag designs, so they align with your sales kickoff theme.
Companies that trusted PerkUp for their event swag
DuckDuckGo
DuckDuckGo leveraged PerkUp for swag items the company gave away during its annual all-hands meeting.
Euna Solutions
Euna Solutions used PerkUp to customize 1,500 branded bouncy balls for a conference. It’s a swag item that made them stand out on the event floor.
Spring Health
For its onsite team gathering, Spring Health chose Stanley Quencher tumblers to celebrate and unite its team for the event.
Key Takeaway
The teams that get sales kickoff swag right start planning it while there’s still time to make changes. Pick the tote, choose the main apparel item, decide who gets the premium items, and get the artwork approved before the production timeline gets tight. Once those aspects are set, the rest of your sales kickoff event swag ideas can follow your sales kickoff theme.
Have your theme, rough headcount, and kickoff date ready? Book a demo with PerkUp, and we can map out the kit, tiers, and production timeline, so you can ensure that your sales kickoff is a raging success.
Frequently Asked Questions about Sales Kickoff
How long does custom sales kickoff swag take?
Custom bulk swag takes about five weeks before it ships: roughly three weeks for production, one week for kitting, and one week for approval. Some products and decoration methods can take longer, so give yourself extra room when you can. On Demand swag takes about three weeks and works better for one-off replacements or last-minute additions.
How do you track swag inventory and fulfillment for a sales kickoff?
You want to know how many items you have, where they're going, and what's already been delivered. PerkUp's dashboard lets you track inventory and shipments by program and destination, so you can see what's headed to the venue, what's going to a hotel, and what's still being fulfilled. That makes it easier to catch a missing shipment before the kickoff starts.
How do you get kickoff swag to reps who can't travel?
Send their swag directly to their homes instead of trying to send extra kits from the event afterward. PerkUp ships to 65+ countries with regional fulfillment across the US, Canada, Mexico, the UK, Europe, India, China, and Australia. That lets remote and international reps get their swag around the same time as everyone attending in person, with duties prepaid wherever possible.
Can you ship kickoff kits straight to the hotel or venue?
With PerkUp, yes, you can. Pre-built kits can ship straight to the venue, depending on where your attendees will be. You can time delivery around the load-in date and track the shipment alongside production, so you know what's arriving and when. Check the hotel's receiving policy early, though. Some charge per box, and many won't hold packages for more than a few days.
What do you give top performers during a sales kickoff?
Go up a price tier instead of adding more items. A Peter Millar quarter-zip or Vuori vest feels more like an award than another tumbler, and the brand makes the difference obvious when it's handed over on stage. If you want something more specific, PerkUp can source specialty items outside the standard catalog, and in-house designers can help with custom packaging or a customized presentation kit.
