Benjamin | Straight Comfort Trousers

Regular price$74.95
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RELAXED STRUCTURE. DAILY VERSATILITY.

Benjamin™ is designed for men who appreciate clean simplicity, breathable comfort, and effortless polish. The soft fabric drapes naturally for all-day ease, while the straight-leg cut delivers a relaxed yet refined silhouette. Built for movement, travel, and everyday moments without compromising presence.

Loose Straight-Leg Silhouette: Relaxed through the leg with a clean, balanced finish that feels comfortable without looking oversized.
Breathable Soft-Touch Fabric: Lightweight construction designed for consistent day-to-day comfort.
Comfort Waistband & Functional Pockets: Easy fit that moves with you, paired with practical storage for essentials.

100% SATISFACTION GUARANTEE

Free Shipping – Available today in selected regions
Secure Payments – Safe checkout with trusted payment methods
30-Day Returns – Easy returns within 30 days after delivery
Customer Support – Always here to help with your questions

A modern everyday essential defined by balance, comfort, and understated refinement.



All orders are shipped free of charge with a track & trace number, handled exclusively by trusted carriers such as UPS, FedEx, and USPS.

Processing Time: 1–2 business days (Mon–Fri).

Delivery Time: 3–9 business days, depending on your location.

You’ll receive a confirmation email as soon as your order ships — including live tracking details to follow your delivery in real time.

All orders are shipped free of charge with a track & trace number, handled exclusively by trusted carriers such as UPS, FedEx, and USPS.

Processing Time: 1–2 business days (Mon–Fri).

Delivery Time: 3–9 business days, depending on your location.

You’ll receive a confirmation email as soon as your order ships — including live tracking details to follow your delivery in real time.

OUR CUSTOMERS TELL IT BETTER THAN WE DO!

Excellent 4.7 / 5
★★★★★

based on 1596+ reviews

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Verified customer
2 days ago

Great color, great fit.

The dark green is bold and I love it. Wide enough to move freely, the cream drawstring adds a nice contrast. Already recommended these to three friends.

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Verified customer
1 week ago

Wore these all weekend and didn't want to take them off.

The olive corduroy texture is subtle and rich-looking. Super comfortable and the fit is relaxed without losing shape. White sneakers are the only way to go with these.

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Verified customer
4 days ago

Best cargo shorts I've owned.

The olive green is the right shade — not too bright, not too military. Comfortable waistband and the length is spot on. Will be living in these all summer.

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Verified customer
2 weeks ago

Solid everyday cargo trouser.

Functional, durable, and the olive color goes with almost everything. Would pair better with a slimmer top but that's on me — the trousers themselves are great quality.

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Verified customer
5 days ago

A statement piece that actually works.

The high waist and wide leg are bold but the grey keeps it wearable. I wore these with a dark top and Converse and felt genuinely cool for the first time in years.

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Verified customer
1 month ago

Relaxed fit done right.

Soft, breathable, and the fit is generous without being sloppy. I wear these most days now. The cat approved too.

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Verified customer
1 week ago

The perfect smart-casual trouser.

I've been looking for something between jogger and chino for years. This is it. The drawstring keeps it relaxed, the straight leg keeps it clean.

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Verified customer
3 days ago

My favorite trousers this season.

The navy waffle fabric is something else. Dressed up or down, they always look sharp. Comfortable enough to wear all day without thinking about it.

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Verified customer
1 week ago

Bold cut, great quality.

These are wide and relaxed but the buttons on the side make them feel intentional. I was skeptical but I get compliments every time I wear them.

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Verified customer
2 weeks ago

Finally, trousers I actually want to wear every day.

I've been wearing these around the house and out to run errands and they look good both ways. The waffle texture gives them structure without feeling stiff. Paired with a white tee and sneakers — effortless.

A lifetime of care. One final collection.

We opened the doors of The Fifth Season when we were barely in our twenties — two people with very little money, a small space, and one shared belief: that clothing should be made to last.

Not for one season. Not until something newer comes along. Made to be worn for years, loved, and handed down.

For decades, that belief guided every piece we selected. No shortcuts. No fast fashion. No compromises on the fabrics, the cut, or the care that went into every garment.

Now, after a lifetime of doing what we love, it is time to rest. James's back has been asking him to slow down for years. Claire's mother needs us close. And if we are honest with ourselves — we are ready. Ready for quiet mornings, for the grandchildren, for the life we kept putting off while we worked.

We thought about selling. But this was never just a business. It was built from our hands, our taste, our care. We could not hand that to someone else and call it the same thing.

So we are closing — properly, and with gratitude. This final collection is everything we have left, offered at the lowest prices we have ever given. Because we would rather these pieces go to people who will truly wear them than sit in a warehouse after we are gone.

When the last piece sells, The Fifth Season closes. Permanently. No relaunch. No new owner. This is our farewell, and we mean it with all our hearts.

— James & Claire ♥

FAQ

All orders are processed within 1–3 business days and delivered within 5–10 business days, depending on your location.

You’ll receive a tracking link as soon as your order ships.

Items must be unworn, unwashed, and in their original condition with tags attached.

To request a return, email support@the-fifth-season.com with your order number.

We accept all major payment options, including Visa, MasterCard, American Express, Discover, PayPal, Apple Pay, Google Pay, and Shop Pay.

All transactions are securely processed.

Yes. Our pieces are designed with a relaxed, modern fit.

For detailed sizing, please refer to the Size Guide available on each product page.

Each piece is produced with trusted manufacturing partners who share our values of quality, craftsmanship, and timeless design.

Every garment is designed to last beyond the season.

FREE FAST SHIPPING

FREE FAST SHIPPING

We are offering free shipping only today. All orders ship with UPS and include full tracking.

24/7 CUSTOMER SERVICE

24/7 CUSTOMER SERVICE

If you have any questions, feedback, or concerns about your order, don't worry! Our customer service team is here to assist you.

30-DAY MONEY-BACK GUARANTEE

30-DAY MONEY-BACK GUARANTEE

At The Fifth Season, you can shop with peace of mind thanks to our 30-day money-back guarantee. Simply return your items within 30 days.

SECURE PAYMENT

SECURE PAYMENT

Your payment information is processed securely. We accept American Express, Apple Pay, Google Pay, MasterCard, Shop Pay, and Visa.