How to Style Combat Boots for a Wine Tasting in 2027

Direct Answer

To style combat boots for a wine tasting in 2027, pair a structured, neutral-toned blazer or denim jacket with tailored trousers or a midi skirt, and finish with a leather crossbody bag and subtle wine-themed accessories. The key is balancing the boots' rugged edge with polished, occasion-appropriate layers. Think slim-fit chinos or a cashmere turtleneck for men, and a silk blouse or fine-gauge knit for women.

What to Wear

The core palette for a 2027 wine tasting leans into earthy, moody tones: olive green, burgundy, charcoal, and cream. Combat boots in matte black or brown leather ground the outfit. For men, a wool blazer from J.Crew or a cotton chore coat from Banana Republic works well. For women, a cashmere-blend sweater from Everlane or a silk midi skirt from Aritzia adds elegance. Key pieces include slim-fit trousers, denim jackets, turtlenecks, and leather totes. Accessories like a wine-red scarf or brass jewelry tie the look to the setting.

For Men

Masculine-presenting women — these looks work for you too.

Below are three age-specific outfit boards for men, each designed to balance the ruggedness of combat boots with the refinement expected at a wine tasting.

The Modern Rustic

Men's · 20s · Wine Tasting · $300–$600

Wool Blazer — Olive Green · Slim-fit, unstructured from J.Crew

Cashmere Turtleneck — Cream · Fine-gauge, lightweight

Tailored Chinos — Charcoal · Slim-fit, cotton twill

Combat Boots — Matte Black · 6-inch, leather lace-up

Leather Crossbody Bag — Brown · Minimalist, small

The Polished Vintner

Men's · 40s · Wine Tasting · $500–$900

Linen Blazer — Beige · Single-breasted, from Banana Republic

Merino Wool Sweater — Burgundy · V-neck, fine-knit

Wool Trousers — Navy · Flat-front, tailored fit

Combat Boots — Dark Brown · 8-inch, waxed leather

Leather Tote — Cognac · Structured, from Cole Haan

The Classic Oenophile

Men's · 60s · Wine Tasting · $700–$1,200

Cashmere Blazer — Charcoal · Two-button, from Bonobos

Oxford Cloth Button-Down — White · Crisp, spread collar

Corduroy Trousers — Olive · Wide-wale, relaxed fit

Combat Boots — Black · Polished leather, cap-toe

Wool Scarf — Wine Red · Lightweight, for layering

For Women

Feminine-presenting men — these looks work for you too.

Below are three age-specific outfit boards for women, emphasizing elegance and versatility while keeping the combat boots as the focal point.

The Edgy Taster

Women's · 20s · Wine Tasting · $250–$500

Denim Jacket — Indigo · Cropped, from Everlane

Silk Blouse — Blush Pink · Camisole-style, draped

Midi Skirt — Charcoal · A-line, wool-blend

Combat Boots — Matte Black · 6-inch, platform sole

Crossbody Bag — Black · Pebbled leather, small

The Sophisticated Sipper

Women's · 40s · Wine Tasting · $400–$800

Cashmere Cardigan — Cream · Open-front, from Aritzia

Silk Shell — Burgundy · V-neck, sleeveless

Wide-Leg Trousers — Navy · High-waisted, crepe fabric

Combat Boots — Dark Brown · 8-inch, smooth leather

Leather Tote — Tan · Structured, from Mango

The Elegant Connoisseur

Women's · 60s · Wine Tasting · $600–$1,000

Wool Blazer — Black · Single-breasted, from Ann Taylor

Cashmere Turtleneck — Ivory · Fine-gauge, fitted

Pleated Midi Skirt — Plum · Silk-blend, mid-calf

Combat Boots — Burgundy · 6-inch, patent leather

Pearl Earrings — White · Small studs, classic

How to Adapt by Age

In your 20s, combat boots can be worn with cropped denim jackets and silk blouses for a youthful, edgy contrast. By your 40s, shift to tailored blazers and cashmere sweaters in muted tones like burgundy and navy for a refined look. In your 60s, opt for structured blazers and pleated skirts or corduroy trousers, with boots in polished leather or wine tones to maintain sophistication.

Common Mistakes to Avoid

• Wearing overly distressed boots – Choose clean, polished combat boots; ripped or heavily scuffed styles look too casual for a wine tasting.
• Pairing with ripped jeans – Opt for slim-fit chinos or tailored trousers instead of distressed denim, which clashes with the occasion's elegance.
• Ignoring the palette – Avoid neon or bright colors; stick to earthy tones like olive, burgundy, and charcoal to match the wine setting.
• Over-accessorizing – Keep accessories minimal: a leather crossbody and subtle jewelry are enough; skip chunky belts or loud prints.
• Forgetting the venue – If the tasting is outdoors, layer with a wool scarf or lightweight trench; indoors, focus on fine knits and blazers.

FAQ

Can I wear combat boots to a formal wine tasting? Yes, if you choose polished leather boots in black or burgundy and pair them with a blazer and tailored trousers or a midi skirt. Avoid matte or distressed finishes for formal settings.

What color combat boots work best for a wine tasting? Matte black, dark brown, and burgundy are ideal. These colors complement earthy wine-tasting palettes and pair well with olive, cream, and charcoal outfits.

How should I clean combat boots before a wine tasting? Use a damp cloth to wipe off dirt, then apply a leather conditioner (like Saphir or Lexol) to restore shine. For suede boots, use a suede brush and protector spray.

Can I wear combat boots with a dress to a wine tasting? Absolutely. A silk midi dress in burgundy or navy pairs well with black combat boots. Add a leather jacket or blazer for a balanced look.

Are combat boots appropriate for outdoor wine tastings? Yes, they are excellent for gravel paths or vineyard terrain. Choose rubber-soled boots for grip and water-resistant leather if the weather is damp.

Bottom Line

Combat boots can be a stylish, practical choice for a 2027 wine tasting when paired with tailored separates and earthy accessories. Focus on polished leather, neutral tones, and layered textures to elevate the look. With the right balance of rugged and refined, you'll fit right in at any vineyard or tasting room.

*Published June 2027 · Updated June 2027*