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Top steep and cheap Deals & Price Drops for May 2026

Explore verified steep and cheap discounts and price drops updated in the last 30 days.

Vans Women's MTE Ultrarange 2.0 SE - Evening Haze, 7.5/9

Vans Women's MTE Ultrarange 2.0 SE - Evening Haze,...

Step into versatile comfort with the Vans Women's MTE Ultrarange 2.0 SE Shoe in Evening Haze. Designed for those who move from city streets to forest trails, these shoes blend athletic performance with rugged durability. The leather and nylon uppers resist scuffs and scrapes, making them perfect for daily wear and light adventures. UltraCush midsoles provide plush cushioning that keeps your feet comfortable during long days, whether you're exploring neighborhoods or running errands. The reverse waffle lug outsoles, wrapped in rubber, deliver reliable grip on pavement, packed dirt, and mixed surfaces. Plus, the responsibly sourced rubber aligns with eco-conscious values. At steep and cheap, we offer gear that performs without breaking the bank. Save big on this versatile shoe that adapts to your lifestyle. Embrace the freedom to explore in style and comfort. Grab your pair today and experience the difference.
$99.95
$39.9860% OFF
Vans Women's MTE Ultrarange 2.0 SE Shoes - Evening Haze

Vans Women's MTE Ultrarange 2.0 SE Shoes - Evening...

Step into all-day comfort and rugged style with the Vans Women's MTE Ultrarange 2.0 SE Shoes in Evening Haze. Designed for those who love to explore both city streets and forest trails, these shoes blend durable leather and nylon uppers with plush UltraCush midsoles for a cloud-like feel that keeps you going mile after mile. The reverse waffle lug outsoles provide reliable grip on mixed surfaces, from pavement to packed dirt, so you can move confidently from errands to light hikes. Responsibly sourced rubber adds an eco-friendly touch without sacrificing performance. Whether you're navigating daily commutes or weekend adventures, these shoes adapt to your lifestyle with ease. Save big on premium outdoor gear at steepandcheap.com, where every day brings unbeatable deals on top brands like Vans.
$99.95
$39.9860% OFF
Scarpa Men's Golden Gate ATR Trail Running Shoe in Black / Lime - Size: 44.5

Scarpa Men's Golden Gate ATR Trail Running Shoe in...

The Golden Gate ATR Trail Running Shoe is our choice for running from door to trail with no hiccups in between. Best suited for mid to long-distance runs on both paved and unpaved, the Golden Gate utilizes proprietary Scarpa tech to prioritize propulsion, braking, grip, and stability for a well-rounded run. The Exo upper and Sockfit design cradle our feet tight for a lightning-fast response while dodging tree roots and hopping brooks. Although the brand's size chart has recommendations for how to choose your size, customer feedback suggests this shoe runs small, we would suggest sizing up if you are unused to a tight performance fit.
$168.95
$92.9245% OFF
Muck Boots Women's Originals Boot in Black / Buffalo Plaid - Size: 6

Muck Boots Women's Originals Boot in Black / Buffa...

Inspired by our iconic Chore Boot, Muck Originals is a collection of light-duty, yet essential footwear. Full neoprene booties are wrapped in soft, hand-laid rubber for comfortable, 100% waterproof protection. Molded PU footbeds with a layer of memory-foam offer maximum underfoot comfort. Further, the footbeds bioDEWIX odor and moisture management insert keeps you fresh all day. The easy on/off design and durable outsole with breasted heels offer traction, style, and performance for life outside.
$139.95
$62.9855% OFF
Xtratuf Women's Legacy LTE Boot in Fossil / Taupe - Size: 7.5

Xtratuf Women's Legacy LTE Boot in Fossil / Taupe ...

This rugged boot from XTRATUF is built for life in Alaska and designed to keep you protected, dry and comfortable no matter where your adventures may lead. The Legacy LTE is inspired by the numerous hand-sewn creations weve come upon throughout Alaska, it includes everything you love about our classic Legacy, in a lighter-weight, slimmer profile. The Legacy LTE features TUFDRY, our signature waterproof breathable membrane, along with a waterproof suede upper making this the ideal all-purpose winter and wet-weather boot. The Legacy LTE offers all day comfort via a dual density open cell foam insert. The updated styling is a fresh take yet offers the same commercial grade performance as the classic Legacy Boot due to is slip-resistant non-marking Chevron outsole.
$155.00
$38.7575% OFF
Vasque Women's Clarion '88 GTX Hiking Boot in Gray / Green - Size: 6

Vasque Women's Clarion '88 GTX Hiking Boot in Gray...

What Our Gearhead® Experts Are Saying:"The Vasque Clarion '88 GTX is the perfect mix of retro style and trail-ready performance. The Gore-Tex lining keeps my feet dry no matter how wet the trail gets, and the dual-density EVA midsole provides great support and cushioning for long hikes. With the Vibram outsole, I get excellent grip even on tricky terrain, making it a solid choice for any adventure."The Vasque Clarion '88 GTX Hiking Boot combines classic style with modern performance, designed to support your every step on the trail. With a waterproof Gore-Tex lining, these boots keep our feet dry even when the conditions are less than ideal. The Vibram outsole provides reliable traction across all surfaces, giving us the confidence to tackle rugged trails and varying terrains. Built with a dual-density EVA midsole, the Clarion '88 GTX absorbs impact and delivers comfort mile after mile, keeping our feet comfortable on long days out. With a durable construction and a timeless look, these hiking boots bring together performance, protection, and style, making them the perfect companion for explorers ready to tackle anything the trail throws their way.
$240.00
$60.0075% OFF
Giro Factor Techlace Road Cycling Shoes in Vermillion / Black - Size: 39.5

Giro Factor Techlace Road Cycling Shoes in Vermill...

What Our Gearhead® Experts Are Saying: "I’ve ridden in the Factor Techlace for years and it’s still my go-to for long road days. The carbon sole is ultra-stiff, but the Techlace system gives it a more natural fit than full-BOA designs. Bonus: the adjustable arch insert really helps with my foot fatigue on hours-long rides."When every watt counts and long rides demand long-lasting comfort, we turn to the Giro Factor Techlace Shoe. With a clever blend of tech and tradition, this road-ready shoe combines the plush feel of laces with the quick adjustability of a BOA® Fit System dial—giving us the kind of micro-tuned fit that adapts mid-ride without skipping a beat. Giro wraps the shoe in a single-piece Evofiber SL upper that’s lightweight, breathable, and sleek, while the stiff EC90 SLX2 carbon outsole puts power directly to the pedals. Underfoot, the SuperNatural Fit Kit lets us fine-tune arch support for a truly personalized fit, and replaceable heel pads extend the shoe’s life even after thousands of miles. At just 210 grams, this is elite-level performance without sacrificing all-day rideability.
$350.00
$87.5075% OFF
Vittoria Cycling Shoes Tierra Cycling Shoe in Black - Size: 38.5

Vittoria Cycling Shoes Tierra Cycling Shoe in Blac...

What Our Gearhead® Experts Are Saying: "I really like the Tierra for gravel because it’s simple, tough, and comfortable. The lace closure is dependable when mud would jam a BOA, and the upper sheds water surprisingly well. They breathe better than I expected, and once broken in they fit like a glove." The Vittoria Tierra Cycling Shoe nods to tradition with a lace-up design while delivering the durability and comfort modern gravel riders demand. Handmade in Italy, the microfiber upper features minimal stitching and a water-resistant finish to protect against splashes, while vents along the sides keep airflow moving on warm days. Reinforced with a vulcanized rubber toe cap, the Tierra is ready for rough, rocky terrain. The carbon composite sole keeps the platform stiff for pedaling, while a rubber tread along the cleat and heel improves traction off the bike. Laces provide a clean, secure fit that’s simple and reliable—even in muddy conditions where dials might falter. Toe spikes are included for added grip on hike-a-bike sections, giving the Tierra a boost of utility for mixed-surface adventures. With its chameleon-like finish, durable construction, and balance of stiffness and comfort, the Tierra is a workhorse gravel shoe that stays true to Vittoria’s Italian heritage while embracing the demands of today’s riders.
$219.98
$55.0075% OFF
Vittoria Cycling Shoes Hera Cycling Shoe in Black - Size: 37

Vittoria Cycling Shoes Hera Cycling Shoe in Black ...

What Our Gearhead® Experts Are Saying:"The Hera is a great shoe for riders who want dependable comfort without breaking the bank. The buckle and dual straps give me a secure fit, the nylon sole is supportive but forgiving, and the synthetic upper flexes just enough to keep my feet comfortable on longer rides."The Vittoria Hera Cycling Shoe is designed for riders who value comfort and control on every ride. Its synthetic PU upper provides durability while allowing natural flexibility in the toe box for a less constrictive fit, making it an excellent choice for long days on the road. The CRS micro-adjustable buckle pairs with dual straps to evenly wrap the foot, giving us a secure fit that’s easy to fine-tune mid-ride. Beneath it all, the nylon sole strikes a balance between efficient pedaling support and comfort, while the included EFC insole adds cushioning and stability. At just 286 grams, the Hera is lightweight enough for spirited efforts yet durable enough for everyday training.
$119.98
$30.0075% OFF
Vittoria Cycling Shoes Rapide GT Cycling Shoe in Blue - Size: 39.5

Vittoria Cycling Shoes Rapide GT Cycling Shoe in B...

What Our Gearhead® Experts Are Saying:"I use these Rapide GTs every week for spin class, and they’ve become my go-to indoor shoes. The rubber touring sole makes walking around the studio easy, and the SPD compatibility clicks right into the bikes without any hassle. They’re comfortable, supportive, and lightweight enough that I don’t even think about my feet mid-session."We count on the Vittoria Rapide GT Cycling Shoes to keep our focus on the workout, not on our feet. Vittoria blends a simple, reliable design with just the right amount of performance for spin sessions and indoor training. The Rapide GT uses a synthetic PU upper that’s supportive and durable, paired with a classic strap closure system for quick adjustments. Underfoot, the SPD-compatible Rubber Touring sole connects easily to indoor cycling bikes while still being practical enough for walking around the gym or studio. With a lightweight build and an EFC insole that adds all-day comfort, these shoes make every session smooth, efficient, and worry-free.
$106.98
$32.0970% OFF
Dynafit Women's Ultra 100 Trail Running Shoe in Nimbus / Black Out - Size: 9

Dynafit Women's Ultra 100 Trail Running Shoe in Ni...

Delivering max cush without the clunk, the Dynafit Ultra 100 Trail Running Shoe keeps our feet happy and our pace on point. The Heel Preloader tech and rockered platform work together to send us into quick and powerful transitions by minimizing heel slip and snapping us onward, while the generous stack of featherweight foam pads every strike and charges every toe-off. Constructed with a larger volume fit, this pair accommodates that long-run swell, while the seamless tongue design minimizes pressure points and hides away the lace ends to keep our fit locked in.
$179.95
$53.9870% OFF
Dynafit Women's Ultra 100 Trail Running Shoe in Nimbus / Black Out - Size: 7.5

Dynafit Women's Ultra 100 Trail Running Shoe in Ni...

Delivering max cush without the clunk, the Dynafit Ultra 100 Trail Running Shoe keeps our feet happy and our pace on point. The Heel Preloader tech and rockered platform work together to send us into quick and powerful transitions by minimizing heel slip and snapping us onward, while the generous stack of featherweight foam pads every strike and charges every toe-off. Constructed with a larger volume fit, this pair accommodates that long-run swell, while the seamless tongue design minimizes pressure points and hides away the lace ends to keep our fit locked in.
$179.95
$53.9870% OFF
SOREL Women's Hi-Line Lace Boot in Geo Yellow / Jet - Size: 6.5

SOREL Women's Hi-Line Lace Boot in Geo Yellow / Je...

We tie our feet into Sorel's Hi-Line Lace Boot for a chic workwear look that keeps us stepping easy all day long. The sleek leather upper molds to our feet, getting more comfortable with age, while the cushy platform softens the ground for a plush ride.
$184.95
$55.4870% OFF
Lowa Women's Corvara GTX Mid Backpacking Boot in Patina Green / Grey - Size: 7.5

Lowa Women's Corvara GTX Mid Backpacking Boot in P...

What Our Gearhead® Experts Are Saying:"I like this boot for long backpacking days when comfort really matters. It feels supportive without being overly heavy, the ankle fit is plush, and the traction inspires confidence on steep descents. It’s a great option for covering serious miles with a pack."When we’re logging long days deep in the backcountry, we want a boot that balances support, comfort, and reliability—and the Corvara GTX Mid Backpacking Boot from Lowa delivers. Built for extended mileage under load, it provides a stable, confidence-inspiring ride that helps us stay focused on the trail ahead rather than our feet. The split leather and fabric upper is paired with a waterproof GORE-TEX membrane to keep moisture out while still allowing breathability. Molded cuffs wrap comfortably around the ankles for a secure, broken-in feel, and the two-zone lacing with X-Lacing technology lets us fine-tune the fit. Underfoot, the DynaPU+ midsole cushions every step while maintaining stability, and the Vibram CORNERSTONE outsole—complete with aggressive heel brakes—adds traction and control on steep, rugged descents. Designed to go the distance and built to be resoled, the Corvara GTX Mid is a dependable companion for serious backpacking adventures.
$274.95
$82.4870% OFF
Vittoria Cycling Shoes Veloce Cycling Shoe in White / Red - Size: 39

Vittoria Cycling Shoes Veloce Cycling Shoe in Whit...

What Our Gearhead® Experts Are Saying: "I like the Veloce because it feels like a race shoe without being overly harsh. The ventilated carbon sole is super stiff and efficient, but the upper is soft and form-fitting so I don’t get hotspots on long rides. The dual BOA dials let me fine-tune the fit exactly where I want it." Blending Italian style with top-tier performance, the Vittoria Veloce Cycling Shoe keeps us pedaling fast and efficiently. Handmade in Italy, the Veloce borrows design cues from Vittoria’s pro-level shoes while maintaining comfort for everyday training. A lightweight, low-stack carbon sole keeps the platform stiff and ventilated, transferring every watt to the pedals while preventing overheating on hot rides. The dual BOA L6 dials let us dial in a secure, micro-adjustable fit across the entire foot, and the supple upper molds comfortably without pressure points. With 3-bolt cleat compatibility, the Veloce is ready to pair with both Look and Shimano SPD-SL setups, making it a versatile option for any road cyclist who values both performance and style.
$253.58
$76.0770% OFF
Evolv Women's Rebel Approach Shoe in Shitake - Size: 6

Evolv Women's Rebel Approach Shoe in Shitake - Siz...

Sometimes we head to the gym and end up at the crag. Evolv's Rebel Approach Shoe has the style and performance we want no matter where we end up. It's a bit burlier than Evolv's casual line of approach shoes, and slightly better-suited for easy trails too.
$99.00
$29.7070% OFF
Scott Women's RC Evo Cycling Shoe in Matt Bronze / Black - Size: 40

Scott Women's RC Evo Cycling Shoe in Matt Bronze /...

Scott's RC Evo Cycling Shoe is designed to chase down breakaways and lead the pack in our local group rides or weekend racing. Its removable ErgoLogic insole with adjustable arch support and metatarsal button delivers a comfortable and customized fit, while the laminated TPU & AirMesh upper is lightweight and breathable. We twist the dual-zone BOA® Li2 Fit System dials for easy on-the-go adjustments to ensure every watt reaches its potential.
$299.99
$90.0070% OFF
Merrell Women's Wrapt Sneaker Mid WP Shoe in Stucco - Size: 9

Merrell Women's Wrapt Sneaker Mid WP Shoe in Stucc...

What Our Gearhead® Experts Are Saying: "I like this shoe when I want natural movement but still need weather protection. It feels light and flexible underfoot, the toe box lets my feet spread naturally, and the waterproof upper handles wet sidewalks or dirt trails with ease. It’s a great balance of barefoot comfort and everyday durability." We lace up the Wrapt Sneaker Mid WP Shoe when we want to move naturally without giving up protection or versatility. Merrell took the fit and philosophy of its barefoot collection and blended it into a low-profile hybrid that feels just as comfortable navigating city streets as it does wandering onto dirt paths. The result is a grounded, flexible ride with a modern, everyday look. Built with Merrell’s Barefoot 2 construction, the shoe keeps our feet in a natural position, encouraging balance and connection to the ground. A waterproof suede and ripstop upper seals out moisture, while a lightweight EVA insole and padded collar add just enough comfort for all-day wear. Finished with a durable Quantum Grip™ outsole, this shoe gives us the confidence to roam wherever the day leads.
$149.95
$50.9866% OFF
Chaco Women's Cushz Sandal in Frond Pacific - Size: 6

Chaco Women's Cushz Sandal in Frond Pacific - Size...

What Our Gearhead® Experts Are Saying:"These sandals are next-level comfy! The extra cushioning makes a huge difference for all-day wear, and the lightweight, flexible design means I barely notice them on my feet. The adjustable webbing gives me a perfect fit, whether I’m walking around town or just lounging outside. They’re my go-to for effortless comfort."Some days call for adventure, but others are all about taking it easy—that’s where the Chaco CushZ Sandal comes in. Designed for laid-back comfort, this ultra-cushioned sandal delivers a soft, supportive ride that keeps our feet happy from morning errands to sunset strolls. With a sleek, minimalist design and pass-through adjustable webbing, the CushZ offers a customized fit without unnecessary bulk. The lightweight, flexible construction moves naturally with us, making every step feel effortless. Whether we're kicking back at the campsite, strolling through town, or relaxing at home, the CushZ keeps comfort front and center.
$79.95
$27.9865% OFF
Forsake Men's Mason Low Shoe in Olive - Size: 10.5

Forsake Men's Mason Low Shoe in Olive - Size: 10.5

An outdoor sneaker with some street style, the Forsake Mason Low contributes everyday comfort to our outdoor and indoor adventures. The Peak-to-Pavement tread provides a solid base of all-terrain traction with Memory Foam footbeds and EVA midsoles layered on top to cushion every step for all-day comfort. We like the look and feel of these everyday outdoor shoes, which also include recycled and responsibly sourced materials to reduce our environmental footprint.
$89.95
$31.4865% OFF
Landed The Overlook Shoe in White Salt Flats - Size: Mens 12.0/Womens 13.5

Landed The Overlook Shoe in White Salt Flats - Siz...

What Our Gearhead® Experts Are Saying: "I’ve been wearing these as my daily go-to when I’m bouncing between errands, travel days, and casual trail walks. The comfort stands out right away—the insole feels supportive without being stiff, and the relaxed fit keeps my feet happy all day. They’ve got enough grip and structure to handle uneven ground while still looking clean around town." We slip into the Overlook Shoe when our days don’t stick to one plan. Landed designed this everyday technical sneaker to move effortlessly from city streets to spontaneous trail detours, making it an easy choice for daily adventures that blend comfort, style, and exploration. From morning coffee runs to sunset walks, the Overlook feels broken-in from the start while still offering the support we want for long days on our feet. Underfoot, Landed’s F3 Ultra Insole delivers cushioned, moldable comfort that adapts to our stride, while reinforced flex points help reduce fatigue as the miles add up. A subtle stabilizing plate adds confidence on uneven surfaces, and the durable rubber outsole grips reliably wherever we roam. Finished with premium suede, recycled details, and a clean silhouette, the Overlook Shoe is built for moving through life comfortably—no matter where the day leads.
$109.95
$38.4865% OFF

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