Bottoms

Shop Simpson Outfitters for men’s bottoms, offering a versatile collection of pants, shorts, and leggings designed for comfort, style, and performance. Whether you need durable outdoor pants, lightweight workout shorts, or comfortable joggers, our men’s bottoms collection has something for every activity and style.

Men's Lounge Wear
Men's Lounge Wear
7 products
Men's Swimwear
Men's Swimwear
13 products
Men's Shorts
Men's Shorts
18 products
Men's Underwear
Men's Underwear
16 products
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  • Shinesty The Peppermint Pimp Canes Shinesty The Peppermint Pimp Canes
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    Shinesty

    Shinesty The Peppermint Pimp Canes

    Shinesty The Peppermint Pimp Canes Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is moisture wicking and breathable. All Modal is not equal. Our proprietary knitting process gives you a more sumptuous Modal per square inch for a softer, better...
    $29.99
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  • Shinesty The Nutty Soldier Shinesty The Nutty Soldier
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    Shinesty

    Shinesty The Nutty Soldier

    Shinesty The Nutty Soldier Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is moisture wicking and breathable. All Modal is not equal. Our proprietary knitting process gives you a more sumptuous Modal per square inch for a softer, better fitting,...
    $29.99
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  • Drake Men's Lounge Pant - Original Bottomland Drake Men's Lounge Pant - Old School
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    Drake

    Drake Men's Lounge Pant

    Drake Men's Lounge Pant After a long day at work or in the field, slip on a pair of Drake Lounge Pants. We made these from a stretchy 100% polyester that is brushed for softness.  The waist is fully elastic and has a draw cord to allow you to adjust...
    $39.99
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  • Burlebo Men's 3-Pack Boxer Briefs Burlebo Men's 3-Pack Boxer Briefs
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    Burlebo

    Burlebo Men's 3-Pack Boxer Briefs

    Burlebo Men's 3-Pack Boxer Briefs Experience all-day comfort and bold seasonal style with the Boxer Briefs Collection. Designed with performance stretch fabric, these boxer briefs provide the perfect balance of flexibility, breathability, and...
    $59.99
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  • Shinesty Men's The Midnights Shinesty Men's The Midnights
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    Shinesty

    Shinesty Men's The Midnights

    Shinesty Men's The Midnights Your waist is now invisible...but the rest of you isn't. So now you look like a magicians-body-saw-trick just walking around. It's unnerving, and also exhilarating. Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is...
    $27.99
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  • Shinesty Men's The Mascot with Fly Shinesty Men's The Mascot with Fly
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    Shinesty

    Shinesty Men's The Mascot

    Shinesty Men's The Mascot with Fly Introducing The Mascot Ball Hammock® with fly, aka the eagle's nest, where your balls will experience an unprecedented level of comfort and support from here on out. It's as if your plums mounted a cloud while...
    $27.99
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  • Shinesty Men's The Front Nine Shinesty Men's The Front Nine
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    Shinesty

    Shinesty Men's The Front Nine

    Shinesty Men's The Front Nine Hit the links in this golf themed Ball Hammock® Pouch Underwear, featuring your own personal caddy to look after your balls. Because unlike in golf, you really don’t want to get a hole in one. Softest Fabric...
    $27.99
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  • Columbia Men's Rapid Rivers Pants - Flax Columbia Men's Rapid Rivers Pants - Flax
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    Columbia Sportswear

    Columbia Men's Rapid Rivers Pants - Flax

    Columbia Men's Rapid Rivers Pants - Flax Brave the elements on the trail with these versatile pants. Comfort stretch fabric makes it easy to move, while UPF 50 protects your skin, giving you one less thing to worry about. Omni-Shade™ UPF 50 guards...
    $49.99
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    Paramount Outdoors Waterproof Rain Pant - Black
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    Paramount Apparel

    Paramount Outdoors Waterproof Rain Pant

    Stay dry and mobile in the worst weather with the Paramount Outdoors MWRP051 Waterproof Rain Pant. Built for outdoor performance, this shell‑style pant features robust waterproof and breathable fabric, fully taped seams to lock out moisture, and durable...
    Was: $59.99
    $34.99
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  • Marsh Wear Men's Fireside Fleece Pants 2.0 - Green Mallard Camo Marsh Wear Men's Fireside Fleece Pants 2.0 - Green Mallard Camo
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    Marsh Wear

    Marsh Wear Men's Fireside Fleece Pants 2.0

    Marsh Wear Men's Fireside Fleece Pants 2.0 When the temps drop low, there’s only one place to go. The Fireside Fleece Pants keeps you warm and comfortable during those long evenings telling tall tales that go until the...
    $69.99
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  • Local Boy Pajama Pants - Dark Olive & Moon
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    Local Boy Outfitters

    Local Boy Pajama Pants - Dark Olive & Moon

    Local Boy Pajama Pants - Dark Olive & Moon A soft and stretchy-enough-to-sleep-in fabric blend naturally makes the LBO PajamaPant ideal for grabbing an easy 10 hours of Z’s. Add in our signature dog and moongraphics and they practically double...
    $34.99
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  • Carhartt Relaxed Straight Rugged Flex Dyed Jean - Concrete Carhartt Relaxed Straight Rugged Flex Dyed Jean - Concrete
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    Carhartt

    Carhartt Relaxed Straight Rugged Flex Dyed Jean

    Carhartt Relaxed Straight Rugged Flex Dyed Jean 11.75-ounce, 65% cotton / 34% polyester / 1% spandex denim Built to move with Rugged Flex® stretch technology Mid-rise sits just below the waist, with a roomy fit in the seat and thigh, and a straight...
    $69.99
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  • Carhartt Duck Bib Overalls - Unlined - Black Carhartt Duck Bib Overalls - Unlined - Carhartt Brown
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    Carhartt

    Carhartt Duck Bib Overalls - Unlined

    Carhartt Duck Bib Overalls - Unlined 12-ounce, 100% cotton ring-spun duck Relaxed Fit Adjustable front-elastic suspenders with webbing slider on straps Updated bib pocket style holds electronics securely Stretch side panels for more precise fit Ledge...
    $99.99
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  • Saxx Vibe Xtra Soft Comfort 6" Boxer Brief - Black Saxx Vibe Xtra Soft Comfort 6" Boxer Brief - Dark Navy Heather
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    Saxx Underwear Co.

    Saxx Vibe Xtra Soft Comfort 6" Boxer Brief

    Saxx Vibe Xtra Soft Comfort 6" Boxer Brief Feel good vibes in best-selling, Vibe Xtra Soft Comfort Boxer Briefs with Stop Drop Technology™ — a barely-there wicking structure built into the BallPark Pouch® — feature No-RideUp...
    $20.00 - $29.99
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  • Kuhl Rydr Lite Klassik - Badlands Khaki Kuhl Rydr Lite Klassik - Badlands Khaki
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    KÜHL

    Kuhl Rydr Lite Klassik - Badlands Khaki

    Kuhl Rydr Lite Klassik - Badlands Khaki Ruggedly durable yet soft and comfortable Cotton blend with just a touch of spandex for comfort Luxurious micro twill cotton with stretch UPF 50+ provides maximum UV protection to covered areas Neither slim nor...
    $94.99
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  • Free Fly Men's Breeze Pant - Cement Free Fly Men's Breeze Pant - Cement
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    Free Fly Apparel

    Free Fly Men's Breeze Pant

    Free Fly Men's Breeze Pant Light, airy, and packed with stretch, our Breeze Collection delivers performance-level comfort and casual, everyday style. The Breeze Pant is a longtime bestseller thanks to the featherweight feel and full-length (but...
    $93.99
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  • Nike Men's Club BB Joggers - Black/White Nike Men's Club BB Joggers - Black/White
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    Nike

    Nike Men's Club BB Joggers

    Nike Men's Club BB Joggers The Men's Nike Club BB Joggers is the perfect choice for any active lifestyle. These Men's Nike Club BB Joggers are designed with comfort and movement in mind and are crafted from lightweight, breathable fabrics. The Men's Nike...
    $59.99 - $64.99
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    Columbia Men's PFG Rambler Water Shorts - Blue Echo Columbia Men's PFG Rambler Water Shorts - Blue Echo
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    Columbia Sportswear

    Columbia Men's PFG Rambler Water Shorts

    Columbia Men's PFG Rambler Water Shorts Omni-Shade™ UPF 50 guards against skin damage using tight fabric construction and modified fibers to block UVA/UVB rays, so you stay protected in the sun Omni-Shield™ repels moisture and resists stains...
    Was: $44.99
    $22.50
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