Finding my First Pair of Jeans

By James Webb

In my first few weeks at university, I quickly realized that only wearing sweatpants won’t cut it. Whether it’s for a group dinner, going to class, or a night downtown, jeans are a staple that every man needs. Finding the right ones can feel like a chore, but once you get your fit, you’ll wonder how you ever went without them.

Step 1: Know Your Fit

Jeans are built around fit, not necessarily the price tag:

• Slim Fit: A go-to for most body types, tapers nicely without being tight.

• Straight Fit: Classic and timeless. Think clean, relaxed lines, ideal for guys with bigger legs.

• Relaxed Fit: Roomier throughout; great for a laid-back vibe or streetwear look.

• Tapered Fit: The modern hybrid: comfortable up top, sharp at the ankle.

Try a few styles before you commit. The perfect jeans should feel snug at the waist, flexible through the thighs, and just skim your sneakers. 

Step 2: Shop by Range

Under $75 — Everyday Essentials

• Old Navy Men’s Slim 360° Tech Stretch Performance Jeans: Super budget-friendly (often ~$30 CAD), good stretch, decent for class or errands.

• H&M Men’s Straight Regular Jeans: Around ~$45 CAD, straight fit, multiple washes, good beginner choice.

• Old Navy Men’s Straight Built‑In Flex Jeans: ~25-35 CAD on sale, roomier thigh area, good if you lift or need leg room.

$80–$150 — Elevated Basics

• Levi’s Men’s 505  Regular Fit Jeans: About ~$47 CAD currently (on sale), which is a great value. A trusted brand, good step-up from super budget.

• Or check the official site for the 511™ fit: Levi’s 511™ Slim Fit Jeans

• Also consider premium denim in this range if you catch a sale.

$150+ — Investment Denim

• Naked & Famous Men’s True Guy Max Brush Straight Fit Denim: ~$265 CAD – a serious investment. Premium fabric, unique fades, high-craftsmanship.

• If you’re planning to keep these for years or build a “go-to” pair, this tier is for you.

Step 3: Style It Your Way

• For Class: Slim fit in a medium wash + white tee + zip-hoodie (smart casual).

• For Night Out: Black tapered/straight jeans + crewneck + clean white sneakers (elevated but still comfy).

• For Game Day / Errands: Relaxed fit + hoodie + sneakers (casual, functional).

Final Thoughts

Your first real pair of jeans isn’t just about style; it’s the item that unlocks many new outfits. It’s that middle ground between comfort and confidence that every guy needs once university life starts to feel a bit more grown-up. Start simple, find your fit, and let the rest fall into place.