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Tailored Fit Pants Deals

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  • Gift Badge For Traveler® COOL<i>MOTION</i> Tailored Fit Wool Blend Dress Pants
    The sale price is   $99.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    These Tailored Fit pants have 37.5? Technology that maintains the optimum microclimate for your body to keep up with your busy schedule. Made by the Traveler? Collection, the 37.5? active particles help your body thermoregulate, keeping you cool when you're hot and stay warm when you're cold. This technology also wicks away moisture at the vapor level, ensuring maximum comfort. Comprised of a wool-blend fabric with a hint of stretch for mobility, these impressive pants are specially finished to resist stains and wrinkles for fuss-free care and wear.
  • Gift Badge For Jos. A. Bank Tailored Fit Comfort Stretch Casual Chinos
    The sale price is   $74.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Level up your look with the versatile and reliable performance of these essential chinos. This pair features a Tailored Fit and integrated stretch fabric for a comfortable feel that moves with you through every appointment. The durable construction features a hemmed finish for a polished appearance that ensures you look great from the morning commute to evening drinks.
  • Gift Badge For Comfort Stretch Dress Pants - Tailored Fit
    The sale price is   $89.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Perfect for the man on the move, these dress pants by Jos. A. Bank feature a hint of stretch and a comfort waistband.
  • Gift Badge For Traveler® Performance Tailored Fit Cotton Blend Flat Front Golf Chinos
    The sale price is   $79.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Think of these Traveler golf chinos as the ultimate wingman for a long day, whether you are lining up a birdie or sitting through a marathon meeting. They pack a 4-way stretch that moves whenever you do, plus a handy shirt gripper to keep everything tucked in while you swing or reach for that second cup of coffee. Because life can be messy, the water-repellent and moisture-wicking fabric helps you stay dry and look sharp through unpredictable weather or high-pressure moments. These aren't just pants; they are a low-maintenance, machine-washable solution for staying comfortable and looking tailored from the first tee to the final dinner reservation.
  • Gift Badge For Wrangler Retro Tailored Fit Straight Jeans
    Online Exclusive
    The sale price is   $89.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    A throwback fit with everyday ease. These Wrangler jeans deliver a relaxed silhouette with a mid-rise and straight-leg opening for that effortlessly worn-in feel. Designed with a classic zip fly and Wrangler's signature 5-pocket styling, this pair is finished with iconic "W" stitching for an authentic Western touch that never goes out of style.
  • Gift Badge For Reserve Collection Tailored Fit Basketweave Linen Blend Drawstring Pants
    The sale price is   $89.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

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    Description:
    Experience smart-casual at its finest with these effortlessly cool pants. From the Reserve Collection, they're comprised of a rich fabric blend that includes breathable linen, sumptuous cotton, and the unparalleled flexiblity of comfort stretch. Styled with a subtle basketweave pattern and a Tailored Fit, their drawstring closure offers just the kind of ease you need after work, while on the go, or at the beach.
  • Gift Badge For Reserve Collection Tailored Fit Stripe Linen Blend Drawstring Pants
    The sale price is   $89.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Experience smart-casual at its finest with these effortlessly cool pants. From the Reserve Collection, they're comprised of a rich fabric blend that includes breathable linen, sumptuous cotton, and the unparalleled flexiblity of comfort stretch. Styled with subtle stripes and a Tailored Fit, their drawstring closure offers just the kind of ease you need after work, while on the go, or at the beach.
  • Gift Badge For Reserve Collection Tailored Fit Basketweave Linen Blend Shorts 9 Inch Inseam
    The sale price is   $69.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Your summer style just leveled up! These Reserve Collection shorts combine a refined basketweave texture with a Tailored Fit for a look that's polished yet easygoing. Featuring a flat front and built-in stretch, they move with you, whether you're off to a weekend getaway or just kicking back in style. Comfort and confidence? These shorts bring both in one smart package.
  • Gift Badge For Reserve Collection Tailored Fit Linen Blend Shorts 9 Inch Inseam
    The sale price is   $69.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Your summer style just got an upgrade! These Reserve Collection shorts mix polished looks with laid-back ease. Featuring a flat front and Tailored Fit, they're designed to move with you thanks to built-in stretch. Perfect for weekends, getaways, or simply relaxing in style, these shorts prove that comfort and confidence go hand in hand.
  • Gift Badge For Reserve Collection Tailored Fit Linen Blend Shorts 9 Inch Inseam
    The sale price is   $69.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Meet your new summer MVP! These Reserve Collection shorts bring sharp style and easy comfort together in one effortless package. With a flat front and Tailored Fit, they deliver a polished look that moves with you, thanks to the built-in stretch. Perfect for weekends, vacations, or just kicking back in style, these shorts prove that looking good can feel great.
  • Gift Badge For Reserve Collection Tailored Fit Linen Blend Shorts 9 Inch Inseam
    The sale price is   $69.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Lightweight linen and soft cotton blend together to create this chic pair of shorts. By the Reserve Collection, they're flattering with a smooth, flat front, a Tailored Fit, and the ease of comfort stretch fabric. Breathable, durable, and versatile, they can go with a Henley on a casual Friday, a cotton tee around town, or a linen-blend sportshirt while cruising on a yacht.
  • Gift Badge For Reserve Collection Tailored Fit Linen Blend Pants
    The sale price is   $89.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Part of the Reserve Collection, these casually cool pants deliver relaxed refinement with an elevated edge. Crafted from a breathable linen‑cotton blend with a subtle basketweave texture, they feel lightweight, airy, and effortlessly comfortable. A tailored silhouette and easy drape lend a polished look, making them a versatile choice for warm‑weather outings, weekend plans, and occasions that call for laid‑back sophistication.
  • Gift Badge For Jos. A. Bank Tailored Fit Cotton-Linen Blend Cargo Shorts 10 Inch Inseam
    The sale price is   $54.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Adventure awaits in these ruggedly handsome cargo shorts, designed for the man who refuses to choose between utility and style. The breathable blend of cotton and linen keeps you cool when the heat is on, while built-in stretch ensures you can move freely from city streets to mountain trails. With a variety of pockets to secure your gear and a sharp, flat-front finish, they provide a dependable go-to for every weekend expedition.
  • Gift Badge For Reserve Collection Tailored Fit Italian Wool Textured Dress Pant
    The sale price is   $129.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    These dress pants from the Reserve Collection offer a refined, modern look with a Tailored Fit that provides a closer feel through the seat and thighs. Crafted from a premium Italian wool blend with a hint of stretch, these pants feature a flat front and a subtle textured weave for added depth. The interior is finished with high-quality detailing, making them a reliable and sophisticated choice for a formal event, a business meeting, or a polished evening out.
  • Gift Badge For Traveler® COOL<i>MOTION</i> Tailored Fit Stretch Tech Shorts
    The sale price is   $49.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    These solid stretch tech pull‑on shorts are designed for laid‑back days that still call for a polished look. With a tailored silhouette and easy pull‑on waist, they strike the perfect balance between relaxed and refined: no effort required. The lightweight stretch fabric moves with you, keeping things cool, comfortable, and flexible from morning errands to afternoon plans. Finished with a 9‑inch inseam for a clean, modern length, they're the kind of shorts you'll want to live in all season long.
  • Gift Badge For Traveler® COOL<i>MOTION</i> Tailored Fit Stretch Tech Lined Shorts 5''
    The sale price is   $49.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    These solid stretch tech pull‑on lined shorts are designed for laid‑back days that still call for a polished look. With a tailored silhouette and easy pull‑on waist, they strike the perfect balance between relaxed and refined: no effort required. The lightweight stretch fabric moves with you, keeping things cool, comfortable, and flexible from morning errands to afternoon plans. Finished with a 9‑inch inseam for a clean, modern length, they're the kind of shorts you'll want to live in all season long.
  • Gift Badge For Jos. A. Bank Tailored Fit Tonal Stripe Drawcord Shorts 7 Inch Inseam
    The sale price is   $54.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Lean into effortless style with these cozy cotton shorts that perfectly bridge the gap between weekend lounge and polished leisure. The subtle tonal stripes add a high-end touch to the relaxed feel, while the easy-going drawcord ensures you stay comfortable no matter how you choose to spend your day. Pair them with the matching shirt for a coordinated vibe, or throw on a simple polo or tee for a sharp, easy look.
  • Gift Badge For Traveler® Performance Tailored Fit Floral Shorts 7 Inch Inseam
    The sale price is   $59.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Get ready to own the weekend in these high-performance floral shorts that bring a bold splash of personality to your summer rotation. Engineered with a lightweight nylon blend and a healthy dose of integrated stretch, these plain front separates keep you moving freely whether you're hitting the boardwalk or the backyard grill. The Tailored Fit ensures you look sharp without feeling restricted, while the moisture-managing fabric handles the heat so you can focus on having a good time. Just pair them with a solid polo and your favorite sunglasses for a look that says you've officially clocked out.
  • Gift Badge For Traveler® Collection Tailored Fit Performance Seersucker Shorts 7 Inch Inseam
    The sale price is   $59.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Designed for warm‑weather comfort with a refined edge, these shorts deliver lightweight breathability in a tailored silhouette. The textured seersucker construction promotes airflow while maintaining a crisp, elevated look. Easy to wear and built for movement, they transition effortlessly from travel days to casual outings, offering polished versatility for everyday summer style.
  • Gift Badge For Jos. A. Bank Tailored Fit Solid Textured Comfort Stretch Dress Pants
    The sale price is   $89.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Designed for a sharp, modern silhouette, these Tailored Fit dress pants deliver polish with built‑in comfort. The flat‑front design keeps the look clean and streamlined, while a subtly textured fabric adds depth and refinement. Crafted from a thoughtful blend of recycled polyester. They offer a smooth feel and flexible wear that moves easily through long workdays and dress wear occasions alike.
  • Gift Badge For Jos. A. Bank Tailored Fit Comfort Stretch Textured Solid Dress Pant
    The sale price is   $89.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Meet the dress pants that work just as hard as you do. These Jos. A. Bank trousers offer a Tailored Fit that keeps you looking sharp without feeling like you're trapped, thanks to a healthy dose of spandex for all-day flexibility. The textured solid finish adds visual interest to stand out from the sea of plain slacks, while the recycled polyester blend has you feeling good about your wardrobe choices. Whether you are sprinting to a meeting or settling in for a long dinner, these pants move with you and hold their shape so you never end the day looking rumpled.
  • Gift Badge For Traveler® Performance Tailored Fit Solid Golf Shorts 7''
    The sale price is   $59.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Designed for polished performance on and off the course, these golf shorts deliver comfort, mobility, and style. Cut in a Tailored Fit with a flat‑front profile, they offer a streamlined look that transitions easily from tee time to clubhouse. The stretch‑enhanced fabric blend provides breathable comfort, flexibility, and durability. They're a versatile essential for warm‑weather rounds and casual outings alike.
  • Gift Badge For Vintage & Black Tailored Fit Ribbed Joggers
    Online Exclusive
    The sale price is   $95.00

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Kick back in comfort and style with these ribbed joggers from Vintage & Black. Designed with a soft, textured finish and an adjustable drawstring waist, they're perfect for lounging at home or stepping out in laid-back fashion. The relaxed fit and cozy feel make them your go-to for effortless everyday wear.
  • Gift Badge For Tailored Fit Stretch Twill Shorts 9''
    The sale price is   $54.50

    Buy 1 Get 1 50% Off! (equal or lesser value)

    Please choose a color.
    Description:
    Experience all-day ease with these Jos. A. Bank Tailored Fit shorts, designed to blend timeless style with modern comfort. Made from soft, stretch twill fabric, they offer a flexible fit that moves with you, whether you're relaxing or on the go. The flat-front design and tailored silhouette provide a polished look without sacrificing comfort, making them a go-to choice for warm-weather wear that feels as good as it looks.