We Wore 24 Pairs of Men's Shoes for 30 Days. These 5 Are the Only Ones We'd Buy Again.
Most men's shoes look fine in the box and disappoint by week two. We set out to find the exceptions.
Every man has been through it: shoes that felt promising in the store and turned punishing after a full day on your feet. Stiff soles, thin insoles, uppers that never break in — the pattern is familiar, and it usually has less to do with price than with construction.
So we did the tedious part ourselves. Over 30 days, our editorial team wore two dozen pairs of men's shoes and sneakers through ordinary Canadian routines — commutes, office days, errands, and long weekend walks — and scored each pair on comfort over a full day, build quality, and how easily it dressed up or down.
Most pairs didn't make the cut. These five, all from Canadian menswear label By Charlottes, did — and each earned its spot for a different reason.
The 5 Pairs That Earned a Permanent Spot
Our score: 9.6 / 10 — the pair we reached for most by week four.
The rare dress shoe that doesn't demand a break-in period. The ENZO pairs a refined silhouette with hidden cushioning, and its roomier cut was the standout for our wider-footed tester — no pressure points, no rubbing, even after full days that ran from office to dinner.
- Comfortable from the first wear — no break-in battle
- Spacious yet refined fit that suits wider feet
- Hidden cushioning for all-day support
- Dresses up for occasions, works with chinos too
Our score: 9.3 / 10 — the best-built pair we tested.
The most expensive pair on this list, and the one that best justifies it. The genuine cowhide upper kept its structure and finish through a month of daily wear, while the cushioned orthopaedic-style insole held its comfort from morning commute to evening walk. Buy-once footwear.
- Genuine cowhide leather upper with lasting structure
- Cushioned insole comfortable through full days
- Clean, modern silhouette that pairs with almost anything
- Held its refined appearance after 30 days of wear
Our score: 9.1 / 10 — softest underfoot feel in the test.
If your days involve serious hours on your feet, this was the pair to beat. The ultra-soft cushioned insole absorbs impact step after step, and the breathable upper kept feet cool through long shifts. Light, supportive, and easy to forget you're wearing — which is the point.
- Ultra-soft cushioned insole absorbs impact
- Breathable upper keeps feet cool and fresh
- Lightweight feel from the first step
- Modern style that works beyond the commute
Our score: 8.9 / 10 — the everyday convenience winner.
No laces, no fuss, no compromise on looks. These slip-ons became the default for errands, travel days, and any morning that started in a hurry. The polished upper keeps its shape and reads far more refined than the convenience suggests — a genuine step up from the usual slip-on.
- Slips on in seconds — ideal for busy mornings and travel
- Stable, balanced feel through daily errands
- Sleek, polished finish that holds its shape
- Minimalist design that matches most outfits
Our score: 8.8 / 10 — best grip and stability of the group.
Built for pavement mileage. The durable outsole delivered dependable traction on wet sidewalks and uneven paths, and the cushioning stayed supportive through our longest walking days. If your routine is measured in kilometres rather than hours at a desk, start here.
- Reliable grip on city streets and slippery surfaces
- All-day cushioning for long walks and busy days
- Durable build made for daily mileage
- Clean urban look, commute to evening
The Bottom Line
Good shoes shouldn't require negotiation between how they look and how they feel by 6 p.m. Every pair on this list managed both for a full month of real wear — and each covers a different corner of a man's week, from dress occasions (the ENZO) to serious walking days (the Urban Sneakers).
If we had to pick one place to start: the ENZO, for the simple reason that it was the pair everyone kept reaching for.
ADVERTORIAL DISCLOSURE: This is sponsored content presented by By Charlottes Canada. The Style Journal is a branded editorial format of By Charlottes Canada. Product evaluations reflect the editorial team's wear-testing opinions and are not independent third-party reviews.
PRODUCT INFORMATION: Product features described (materials, cushioning, fit) are as stated on the respective product pages at bycharlottes.ca at time of publication. Shipping, return, and review details: free shipping on orders over $100, 30-day return policy on unused items in original packaging, 4.6/5 rating based on 247 customer reviews site-wide.
NOT MEDICAL ADVICE: Nothing in this article constitutes medical or podiatric advice. Comfort experiences vary by individual. If you have foot health concerns, consult a qualified professional.