9 Best Men's Shoes for Fall & Winter 2019 | Boots, Sneakers, Slip Ons and More

About this video

McGoff presents a comprehensive guide to selecting footwear for fall and winter, explaining that cold-weather shoes should match the bulkier silhouettes and richer textures of layered seasonal outfits. He recommends eight shoe categories—chukka boots, work boots, moccasins, minimal sneakers, retro trainers, Chelsea boots, derby shoes, and loafers—with specific brand examples across various price points to help men build a versatile cold-weather shoe collection.

Key takeaways

• McGoff argues that fall and winter shoes should complement the bulkier fabrics and textures of layered outfits, with earth-tone colors and interesting materials matching the seasonal aesthetic
• McGoff recommends multiple shoe categories including chukka boots, work boots, Chelsea boots, and loafers, suggesting that options like Thursday Boot Company’s Duke and J.Crew’s desert boots offer both style and durability
• McGoff advises wearing loafers year-round with thick wool socks in fall and winter, and suggests a simple sock-matching rule: choosing socks one shade darker than pants in the same color family creates a cohesive look

Episode details: published November 14, 2019 · 78K views · 14:28 long. Summary written by Self Growth Videos from the episode itself. The style advice summarized here is Brock McGoff’s own teaching and opinion, presented for education; product recommendations are his, not ours. Summaries are written by Self Growth Videos from each video itself.

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