Fall Style Preview: Dress Shoes for the Holiday Season

As the leaves turn and temperatures drop, our footwear needs shift dramatically. The casual loafers and lighter leathers of summer give way to richer tones, sturdier construction, and styles that can handle both a boardroom meeting and a holiday cocktail party. I'm Michael Torres, Senior Footwear Specialist at CSL Shoes, and after fifteen years in the industry, I can tell you that the fall-to-winter transition is the most exciting time of year for men's dress shoes.

Whether you're headed to a Thanksgiving dinner, an office holiday party, a Christmas gathering, a Hanukkah celebration, or ringing in the New Year, the right pair of dress shoes ties your entire look together. Here's my comprehensive guide to navigating the holiday season in style.

The Fall Transition: From Summer to Holiday Season

The shift from summer to fall footwear isn't just about swapping tan for dark brown. It's a complete change in how you think about your shoes. Summer forgives a lot — lighter materials, casual silhouettes, minimal structure. Fall and winter demand intention.

Start by assessing what you already own. If you've built a solid foundation collection, you likely have a black oxford and a brown derby that will serve you well through the season. But the holiday calendar brings a range of dress codes that might push you beyond the basics.

The key principle for fall footwear: invest in versatility. A single well-chosen pair in the right color and style can carry you from a Tuesday client meeting through a Saturday evening holiday party. That's where understanding the season's color palette and style codes becomes essential.

Color Trends for Fall and Winter

Color is where the fall season really comes alive for dress shoes. While black remains the foundation for formal events, the real story this year is in the rich, saturated tones that complement fall and winter wardrobes.

Burgundy and Oxblood

If there's one color that defines the holiday shoe season, it's burgundy. Oxblood dress shoes strike the perfect balance between distinctive and versatile. They pair beautifully with charcoal and navy suits, stand out against dark denim, and carry just enough personality for a holiday party without veering into costume territory. A burgundy oxford or monk strap is my top recommendation for anyone looking to add a single holiday-season shoe to their rotation.

Dark Brown and Espresso

Dark brown is the workhorse of the fall wardrobe. It's warm enough to feel seasonal, neutral enough to pair with nearly anything, and appropriate for every dress code from business casual to semi-formal. For Thanksgiving gatherings especially — where the vibe tends toward polished but relaxed — a dark brown derby or loafer is hard to beat.

Black

For black-tie holiday galas, New Year's Eve celebrations, and formal religious services, classic black remains the standard. A well-polished black oxford communicates respect for the occasion. If you only own one pair of dress shoes, make it black — but if you're building out a holiday rotation, let the other colors do the heavy lifting for less formal events.

Navy

Navy dress shoes are having a moment, and for good reason. They offer a sophisticated alternative to black for semi-formal holiday events, pairing especially well with grey suits and earth-toned fall palettes. Consider a navy loafer or whole-cut oxford for holiday office parties where you want to stand out without overdressing.

Dress Shoes for Every Holiday Occasion

Thanksgiving Gatherings

Thanksgiving sets the tone for the season. The dress code typically falls somewhere between smart casual and business casual — you want to look put together without looking like you came from the office. My recommendation: a dark brown or tan derby or loafer. The open-lacing of a derby keeps things relaxed, while the slip-on convenience of a loafer works perfectly when you might be moving between rooms (or helping in the kitchen).

The Esse Comfort range is particularly well-suited here — cushioned insoles mean you can stand and socialize for hours without fatigue, and the classic styling keeps you looking sharp.

Holiday Office Parties

The office holiday party is where most men get tripped up. Too casual and you look like you didn't make an effort. Too formal and you look out of touch. The sweet spot: a monk strap or a cap-toe oxford in burgundy or dark brown. Monk straps, with their distinctive buckle closure, add visual interest without being flashy — exactly the kind of detail that gets noticed at a holiday gathering.

Pair them with dark wool trousers or a navy suit, and you've hit the mark. Check our color matching guide for specific suit-and-shoe combinations that work for these occasions.

Christmas and Hanukkah Celebrations

Religious holiday gatherings call for respectful, polished footwear. For church services, synagogue visits, or family celebrations, lean toward classic silhouettes in traditional colors. A black or dark brown oxford works universally. If the event is more family-oriented and relaxed, a polished loafer in dark brown or burgundy strikes the right tone — dressy enough to show respect for the occasion, comfortable enough for a long evening with family.

Wizfort offers several classic oxford and derby options with refined detailing that suit these occasions perfectly — understated elegance that lets the event, not your shoes, be the focus.

New Year's Eve

New Year's Eve is your chance to go bold. This is the one night of the year where a patent leather oxford, a velvet loafer, or a high-shine whole-cut shoe isn't just acceptable — it's expected. If you've been eyeing something with a bit more personality, December 31st is the night to wear it.

For formal New Year's galas, a classic black patent oxford remains the gold standard. For rooftop parties and restaurant celebrations, consider a polished black or burgundy whole-cut shoe. The clean, seamless silhouette looks modern and pairs well with slim-cut suits and tuxedos.

Formal vs. Semi-Formal Holiday Events

Understanding the distinction saves you from overdressing or underdressing:

• Formal (black tie, galas, formal dinners): Black oxfords, patent leather, or high-polish calfskin. Closed lacing is traditional. Keep it classic.
• Semi-formal (cocktail parties, upscale dinners, holiday fundraisers): Burgundy or dark brown oxfords, monk straps, or polished derbies. This is where you can introduce color and texture.
• Smart casual (Thanksgiving, family gatherings, casual office events): Loafers, suede derbies, or casual monks in brown, tan, or navy. Comfort matters here — you'll likely be on your feet.

Browse our full collection to find options across every dress code and price point.

Material Considerations for Cold and Wet Weather

The holiday season means cold temperatures, rain, sleet, and sometimes snow. Your shoes need to handle it all while still looking polished when you arrive at the event.

Leather Types

Full-grain calfskin remains the top choice for dress shoes in any season, but it requires extra attention in winter. Apply a quality waterproofing cream or wax before the season starts, and reapply monthly. For shoes you'll wear in genuinely wet conditions — walking to a restaurant in the rain, for example — consider shoes with a rubber sole or a leather sole with a rubber half-sole added for traction and water resistance.

Our guide on leather soles vs. rubber soles breaks down the trade-offs in detail, but for winter specifically, I lean toward rubber or combination soles. The grip on wet pavement alone is worth it.

Suede in Winter

Contrary to popular belief, suede can be worn in fall and winter — it just requires preparation. A good suede protector spray creates a water-resistant barrier, and the napped texture actually works beautifully with fall fabrics like tweed, flannel, and corduroy. That said, save suede for events where you won't be trudging through slush. A suede loafer for an indoor holiday party is a great choice. A suede oxford for a walk across a snowy parking lot is not.

Styling Dress Shoes with Fall and Winter Outfits

The right shoe completes an outfit. The wrong one undermines it. Here's how to match your holiday footwear with the season's key wardrobe pieces. For a deeper dive, see our complete styling guide.

Wool Suits

A wool suit is the foundation of cold-weather formal dressing. Pair charcoal wool with black or burgundy oxfords. Navy wool suits open up more options — dark brown, burgundy, or even navy shoes all work. The texture of wool invites slightly richer shoe colors than you might choose in warmer months.

Velvet Blazers

The velvet blazer is a holiday staple, and it demands shoes with some refinement. A polished black or burgundy monk strap complements the texture of velvet without competing with it. Avoid overly casual shoes — a velvet blazer with scuffed loafers sends mixed signals. Patent leather, high-shine calfskin, or a clean cap-toe oxford are all strong pairings.

Overcoats and Topcoats

When you're wearing an overcoat, your shoes are one of the few style details that remain visible. This makes shoe choice even more important. A camel overcoat pairs beautifully with dark brown or burgundy shoes. A charcoal or black topcoat works best with black or deep oxblood. Think of your shoes as the anchor point that ties your outerwear to your suit beneath.

Smart Casual Winter Looks

Dark denim, chinos, or flannel trousers with a sport coat — this is the uniform for most holiday gatherings. A Benelaccio loafer or derby in dark brown works perfectly here. The brand's balance of classic styling and modern comfort makes their shoes ideal for occasions where you need to look polished but not overdone.

Care Tips for the Holiday Season

Your shoes will take a beating this season. A few minutes of maintenance protects your investment and keeps you looking sharp through every event.

• Waterproof before the season starts. Apply a wax-based waterproofing product to all leather dress shoes. Reapply every three to four weeks during heavy use.
• Use cedar shoe trees. After every wear, insert cedar shoe trees. They absorb moisture (critical in winter), maintain shape, and prevent creasing. This is the single most important thing you can do for your shoes.
• Rotate your shoes. Never wear the same pair two days in a row. Leather needs at least 24 hours to fully dry after wearing. During the holiday season, when you might attend events on consecutive nights, having two or three pairs in rotation is essential.
• Clean salt stains immediately. Road salt is leather's worst enemy. If your shoes pick up salt, wipe them down with a damp cloth as soon as possible, then apply conditioner once dry.
• Store properly. Keep shoes in a cool, dry place away from direct heat sources. Never dry wet shoes near a radiator or fireplace — rapid drying cracks leather.

For a complete care routine, our leather shoe care guide covers everything from daily maintenance to seasonal deep conditioning.

Building Your Holiday Rotation

If I had to choose three pairs to carry me through the entire holiday season, here's what I'd pick:

1. Black cap-toe oxford — Covers all formal events, religious services, and New Year's Eve. The most versatile single dress shoe you can own.
2. Burgundy monk strap or derby — Handles office parties, cocktail events, semi-formal dinners, and smart casual gatherings. Burgundy's versatility across dress codes makes it the hero of the holiday season.
3. Dark brown loafer — Perfect for Thanksgiving, casual family gatherings, and any event where comfort matters as much as style. A slip-on silhouette with a cushioned sole — like those in the Esse Comfort line — means you can socialize for hours without thinking about your feet.

This three-shoe rotation covers every dress code from black tie to smart casual, every color palette from charcoal to camel, and every occasion from a quiet family dinner to a packed New Year's Eve gala.

Final Thoughts

The holiday season is when your wardrobe works hardest, and your shoes are the foundation. Invest in quality, choose colors that complement your existing wardrobe, and take care of your leather — and you'll walk into every gathering this season with confidence.

Explore our full collection of men's dress shoes to find the perfect pair for your holiday calendar. And if you're still deciding between an oxford and a derby, or wondering whether monk straps are right for your style, our complete guide to men's dress shoes will help you decide.

Here's to a well-dressed holiday season.

— Michael Torres, Senior Footwear Specialist, CSL Shoes