Winter workwear starts from the ground up, so of course, having the right men’s winter shoes is key this time of year. Footwear isn’t just an accessory; it’s the anchor of your professional wardrobe. The perfect pair gives you warmth, keeps you safe on slippery streets, and ties your outfit together.
If you need help getting your shoe selection into gear, this guide is for you. Next Level Wardrobe’s founder, Cassandra Sethi, is an expert stylist known for helping clients of all ages, sizes, and industries look their best. From years of styling high-performing professionals, she knows exactly which pieces strike the ideal balance between function and style.
Here are five must-have shoes for men with her stamp of approval for staying professional at the office this winter.
1. Winter-Ready Leather Dress Shoes
Product by BOSS, shop here.
Leather men’s winter dress shoes are basically a non-negotiable for winter office wear. They give off sophistication whether you’re leading a stand-up call or attending a formal holiday party.
Partner these versatile shoes with a tailored business suit or elevate a smart casual ensemble like jeans and a quarter-zip sweater. We recommend opting for darker tones like black or deep brown for maximum versatility.
NLW tip: Dark colors go with everything and match the wintry vibe.
2. Chill-Resistant Chelsea Boots
Product ALLSAINTS, shop here.
Need a winter shoe MVP? Look no further than the Chelsea boot. Their sleek, slip-on design and form-fitting profile are ideal for busy morning and office commutes. The tailored silhouette keeps your outfit sharp and avoids extra bulk.
The best part? These boots can go from desk to dinner in a cinch. They’re dressed up while current, easily partnering with slacks, trousers, jeans, and chinos.
NLW Tip: Invest in a waterproof pair to keep your feet dry and warm, no matter the forecast.
3. All-Season Loafers
Product by Allen Edmonds, shop here.
Loafers are a go-to if you don’t live in a snowy climate or your office has a more relaxed vibe. They’re a natural choice for casual Friday winter office shoes.
(Work at a West Coast Office? These will fit the dress code just fine.)
Look for loafers with insulation or lined interiors if you need added warmth during the chilly months. Wear them with slim-fit trousers and an easy-going cardigan.
NLW Tip: Choose loafers in suede or leather for a texture that complements winter fabrics like cashmere wool or flannel.
4. Snowy Sneakers
Product by Giuseppe Zanotti, shop here.
Yes, sneakers can be office-appropriate winter work shoes and a must-have for any guy’s power casual wardrobe.
Are they practical for winter? Definitely—if you choose the right pair and consider your local climate.
In areas prone to black ice or sleet, you might need to save sneakers for drier days or opt for pairs with excellent traction.
For most offices, sneakers offer a modern, minimalist option that balances all-day comfort and style. Stick to neutral colors like black, grey, or white for versatility, and select designs with waterproof materials or insulation to handle winter conditions.
NLW Tip: Avoid flashy logos or bold patterns when selecting men’s office shoes for winter. Keep your choices subtle and clean for a refined touch.
5. Cool Chukka Boots
Product at Neiman Marcus, shop here.
Chukka boots hit the sweet spot between casual and professional winter shoes for men. Made from leather or suede, these versatile, low-profile boots go with everything from chinos to dress pants. They are the casual and practical version of dress shoes.
Seek out chukkas with insulated interiors for cold commutes, or wear a lightweight pair if you live in a warmer climate.
NLW Tip: Waterproof chukka boots are a must for keeping your feet dry through cold and rainy winters. Again, we recommend opting for dark, neutral colors like brown and black for maximum versatility.
Simplify Men’s Winter Shoes with the NLW Style System
Choosing office shoes for men doesn’t have to be complicated. Forget keeping up with trends or buying an excessive number of shoes—the key is to keep it simple.
That’s where the NLW Style System comes in. One of its core principles is focusing on core colors: black, white, navy blue, and gray. These neutral tones pair effortlessly with any outfit and with each other.
We recommend:
- Core Colors | 45% of your wardrobe
- Tonal Colors | 35% of your wardrobe
- Accent Colors | 20%
When it comes to shoes, stick primarily to core or tonal colors. This ensures versatility and eliminates the need for a cluttered shoe collection.
Follow this approach and quickly find stress-free, stylish office footwear options.
Keep Your Style Evergreen with NLW
Ready to elevate your winter work wardrobe beyond men’s winter shoes? Our Next Level Wardrobe styling services for men can help you find the right outfits for your lifestyle. We’ll help you learn to dress yourself for the office and beyond. Every professional deserves to confidently walk into a room (wearing the right pair of shoes). Get styled today!
