Not everybody is comfortable buying "renewed" or "refurbished" products, but you can sometimes get a much better deal on a product if it's listed as renewed. I personally haven't had an issue buying renewed products from Amazon or Best Buy. The deals listed here are mainly from Amazon, which says, "Renewed products work and look like new" and are backed with a 90-day Amazon Renewed Guarantee. Sometimes the box may be generic and accessories like the headphones included with phone may also be generic.
Best Buy uses similar language for its Geek Certified Refurbished products: "Refurbished products are repaired and restored to a like-new state (may have minor scratches), either by one of Best Buy's in-house repair centers, the manufacturer or a third-party refurbishment company. The products are verified to work properly and include all essential parts and accessories (original or comparable substitutes). They're also backed with a 90-day warranty.
Note that I've used or reviewed all these headphones -- albeit new versions of each.
They've been overshadowed by the new AirPods Pro, but some runners and gym rats may well prefer the ear hook design that keeps these true wireless headphones in place during any activity. The price on these fluctuates between $130 and $150. It's also worth noting that new version, which lists for $250, is frequently discounted to $200. That's why we're saying the savings is $50 rather than $100.
Amazon is selling Samsung's popular Galaxy Buds for $105, but Best Buy has them for $70 if you opt for Geek Squad Certified Refurbished version.
The Jabra's Elite 65e is a neckband-style headphone that features active noise cancellation. When it came out in the spring of 2018, it was one of the first headphones to feature Bluetooth 5.0 and carried a list price of $200. The noise-canceling feature is only so-so, but the headphone sounds decent and offers good call quality along with a comfortable fit. You can pick it up for as low as $35.
Best Buy has the new version AirPods with wireless charging case on sale for $170, but if you go the refurbished route you can save $35.
Jabra recently released its new Elite 75t ($180), which is smaller than the 65t and features better battery life and USB-C charging. If you can't afford that, there are some deals to be had on the earlier Elite 65t, which frequently gets discounted to somewhere between $100 and $120 (new). The renewed version is currently selling for $68.
If you're looking for a solid pair of on-ear headphones for not much money, the renewed version of the Plantronics BackBeat Fit 505 is a nice deal at $30. It sounds quite decent and is fairly comfortable for an on-ear model.
The Sony WH-XB900N Extra Bass has a similar design to the WH-1000XM3 and shares many of its features but costs $110 less. It's a comfortable headphone, has USB-C charging, good battery life and effective noise cancellation that's not quite as good as the 1000XM3's. It works decently as a headset for making calls, and the sound quality is quite good as long as you don't mind a preponderance of bass. The gray version is the model discounted on Amazon.
The Sony WH-H900N is also called the h.Ear On 2. It's a better headphone than it gets credit for. While its noise-canceling function isn't quite as good as the WH-1000XM3's -- and it isn't quite as comfortable -- it's well built and is an impressive-sounding headphone.
The Sony WF-1000XM3 is one of our favorite true wireless earphones (we only wish its call quality was a little better). It retails for $230 but the renewed version goes for a more reasonable $150.
Bang & Olufsen Beoplay H4 Wireless Headphones were became available in a second-gen model for $300. This first-gen model, which is an excellent Bluetooth over-ear headphone (no noise cancellation), can be had for as low as $105 if you buy it renewed. Best Buy is selling it for $190 new. We have see the renewed version selling for as low as $90 back in September.
The Beoplay H9i is the second generation of Bang & Olufsen's over-ear noise-canceling headphones. The latest model (third generation), now simply called the H9, has some small upgrades, including better battery life. But the H9i is still an excellent wireless noise-canceling headphone that's comfortable to wear. You can buy it new for around $275.