The headphone market is packed tighter than Chris Farley in a navy blazer, thanks in part to the explosion of digital music — salud, iTunes, Spotify and The Pirate Bay — not to mention the business savvy of a few enterprising rhyme spitters (what up Dre?). Lucky for you, we’ve scoured the headphone market in search of the best over- and on-ear headphones at a critical price point: $250. That may still sound steep to compared to those traumatized ear pods coated in your lint, but it’s unquestionably where the serious values lie: just enough skin in the game to separate the audio trash from the treasure, with anything worth more dough just serving as aural gravy, baby. Read our picks after the break and prepare for Michael Mcdonald jam sessions to get a hell of a lot more soulful.

Harmon Kardon BT Headphones

Harmon Kardon’s new BT headset is designed with iOS users in mind, offering 12 hours of wireless playback and complete control over tunes, calls and Siri thanks to on-ear controls and an integrated mic. Impressively, our tests proved the set can maintain a connection to broadcasting iOS devices even at up to one hundred feet away, allowing impressive roaming flexibility. While wireless audio quality is definitely passable, bass control, mid-range distortion and treble clarity greatly increased when using the included connection cable, proving that cutting the cord does come at a slight cost of fidelity. The bold, retro square ear cup design may not be ergonomic or for everyone stylistically, but high-end detailing in the steel band and leather headband pad (designed with internal moving hinges and extenders rather than a lengthening arm) exudes a premium look that defies the $250 price tag. All said, the BTs pack plenty of flexibility for the modern iPhone user with rich audio prowess.

Pros: Bluetooth, on-ear controls and an integrated mic are ideal for smartphone owners looking to cut the cord while taking calls or listening to tunes.

Cons: Audio quality greatly improves when using a cord versus Bluetooth. The large, retro square ear cups aren’t exactly ergonomic or stylish.

Buy Now: $250

Urbanears Zinkens

Urbanears has made a niche in a crowded market by offering clean, stylish headphones to the cloning hipster masses. The Zinkens follow the same recipe, but were developed to cater specifically to DJs on a budget. Valuable features include swiveling ear cups that collapse for travel and a robust Kevlar core turncable plug with both 3.5mm and 6.3mm plugs — ideal for iPods, serious hifi gear and so-called ZoundPlug, which allows multiple sets of Zinkens to daisy chain together for shared listening. The ear cups definitely teeter on the edge between on-ear and over-ear design, but are still quite comfortable and block out a fair amount of noise. Audio quality is punchy and clear — excelling on bass-heavy tracks all without killing nuances in other genres ranging from classical to pop. At $140, they’re a solid mid-tier entry, especially for those into color, making them ideal for buyers who prefer their technology to exude its own sense of style.

Pros: Bold colorways are a nice alternative to standard black. Unique ZoundPlug and turncable features are pluses for traveling audio nerds who switch between hifi and portable gear, or like to share tunes with other listeners.

Cons: The perfectly circular earcups teeter on the edge of on-ear and over-ear design, and may not fit comfortably on all buyers.

Buy Now: $150

TMA-1 Studio

As their name implies, TMA-1 Studios were built for a new breed of rock star, a.k.a the globe-trotting producer, and as such, have been re-tuned to output a more neutral and balanced sound signature while still maintaining the striking matte black silhouette of the original DJ-honed TMA-1s. Physically, large PU foam ear cups provide solid noise isolation in a lightweight package that’s optimized for long-term comfort — despite feeling slightly wobbly and flimsy to the touch. Proper studio mastering requires an obsessive focus on detail, and for that goal, these cans are a bit of mixed bag. Their great low- and mid-end response is immediately noticeable, as is the enhanced separation and wide sound stage. Audio quality at the high-end feels somewhat veiled, though. Given these factors, it’s clear that the TMA-1s are particularly optimized for specific genres including EDM (electronic dance music) and hiphop. Since ear fatigue usually results from prolonged high frequency exposure, these sets do feel better over prolonged listening sessions. Compared to competing headphones in this price range, the ability to purchase replacement connection cables and ear cups gives this set a leg up in terms of longevity, ensuring interested buyers get years of head bobbing out of their investment.

Pros: Eye-catching, matte black design will turn heads. Available and affordable replacement parts insure these headphones can perform well for years to come.

Cons: Plastic and rubber build has a fragile feel. Audio quality is still slightly bass heavy and geared towards certain genres.

Buy Now: $250

Pioneer SE-MJ591

These premium closed-back travel headphones technically list for more than $250, but can easily be found online for far less. Pioneer bills the SE-MJ591 as their top-of-the-line audio headphone, and they certainly look the part — thanks to hefty matte black plastic and aluminum alloy metal accents that build a solid but stout feel that’s also fairly lightweight. The included carrying case is a notable perk and one of the nicest we’ve seen, with a protective hard exterior and molded interior for securing the headphones when collapsed. Sound-wise, the 40mm drivers featuring aerospace-grade plastics deliver precise tones across the spectrum; refined audio playback should appeal to purists who prefer to let the music speak for itself. These headphones feel as if they were born in a first class lounge, making them an ideal alternative for those on the go and looking to distinguish themselves in a sea of Bose. If you wind up taking the plunge, however, be sure to flatten the ear cups when resting the set on a table, since we learned the hard way that the aluminum alloy’s finish can easily be scratched off.

Pros: High quality, luxurious look and feel. Crisp, refined audio signature.

Cons: Aluminum alloy ear cup mounts easily scratch. Connection cord is shorter than other models.

Buy Now: $250

Grado SR 225i Prestige Series Headphones

Grado Labs’ headphones are the darlings of the audiophile world for good reason. All of their headphones are hand-built in Brooklyn, NY, and boast highly dynamic and precise sound stages that are perfect for any genre of music. The 225i (the i stands for improved) is an update to the original 225, which falls in the middle of their prestige lineup and was produced for a whooping ten years. All-new drivers and a fortified ear cup design are the most notable changes in the set. A beefy connection cord with a gold-plated 6.3mm plug is great news for hifi geeks, but it’s frustrating that Grado doesn’t provide an adapter for connecting to more prevalent 3.5mm jacks on smartphones and computers. As expected, the 225i produces detailed and dynamic sound with exceptional treble detailing (verging on bright) that’s quite impressive for the price. Bass response is somewhat light in today’s age of booming cans, but much of this perception likely stems from the wide open sound stage. Though they’re definitely full-sized, the headphones don’t need amplification for great sound. Unfortunately, their open-backed design also leaks in external sound, which distracts from the listening experience in louder environments. Value-conscious buyers should rest easy knowing that Grado will repair any of its full-sized headphones for a flat fee of $40, easily giving the 225i a shelf-life of a decade or more.

Pros: Built by hand in Brooklyn with an affordable and time-honored service policy. Superb sound quality with exceptional treble detailing.

Cons: Requires a 6.5- to 3.5mm adapter for use with non hifi components such as smartphones and computers. Open ear design allows external noise in.

Buy Now: $225

California Headphone Company Silverados

If you want a pair of headphones that provide great sound and can also be used as a self-defense bludgeon, California Headphone Company’s Silverado ($226) over-ear headphones should be on your radar. The Silverado has all the bells and whistles of solid mid-tier ‘phones: 40mm drivers, a response range of 20-20,000kHz and a handy splitter on its wiring for sharing beats with friends. Sound quality is solid but not exceptional, with clean treble and a well-balanced, thump-if-needed bass presence. As previously alluded, the headphones are not by any means dainty. What’s not sharp-looking leather on the Silverado is die-cast metal. Hinges allow for moderate folding, but make no mistake: these heavy-duty hitters belong on a desk or stand, not your carry-on bag. Amazingly enough, rugged construction yields nicely to a comfortable fit; leather ear cups press firmly on the head — you won’t forget they’re on — but don’t irritate, even after long listening.

Pros: Strong construction that you won’t worry about breaking, without sacrificing comfort.

Cons: Bulky and heavy. Solid but not exceptional sound.

Buy Now: $226

Sennheiser HD 25-1 II

A decade-plus life span in the tech world is virtually unheard of, but that hasn’t stopped Sennheiser’s classic HD 25-1 II from surprising listeners year after year. Though they’re officially labeled as DJ headphones, the feathery light (5oz) 25-1s work just fine for the everyday iPod user thanks to a rotatable capsule for one-ear listening. Overall sound quality is smooth and transparent, with tight, accurate bass that’s more punchy than powerful and avoids bleeding into the neutral mid-range. A relatively narrow sound stage is our only true gripe with the listening experience, but they’re still one of the most versatile pairs of portable headphones we’ve ever encountered — especially for the price. The lack of collapsible design is one area in particular where these headphones show their age, although the unique split headband does provide a solid feel and helps to distribute the set’s noticeably strong clamping force. That squeeze on the noggin helps with noise isolation, which is quite good for a on-ear set. The simplistic design also comes with an added benefit for the DIY set, since every part is user replaceable. If audio quality bang for the buck is the key deciding factor, you’ll be hard pressed to do better than these.

Pros: Amazing audio quality for the price with excellent sound isolation for an on-ear design. All parts are user replaceable.

Cons: They don’t collapse for travel. Both the pleather and velour earpads lack in comfort compared to competing sets.

Buy Now: $190