Planning a Friendsgiving at a vineyard is all about finding the perfect outfit that combines style, comfort, and a touch of warmth for those cool autumn vibes. My outfit for this special day—a vineyard trip with friends by party bus from DC—hits all the marks for the occasion. With a carefully chosen blend of classic pieces and trendy accessories, this look is both photo-ready and practical. Here’s a breakdown of each item, why it works for a vineyard Friendsgiving, and some tips to get your fall fashion on point.
Denim Shirt Dress||Oversized V Neck Knit Sweater Vest||Pattern Tights||Frye Veronica Booties||Oversized Leather Jacket||JW PEI Women’s Elise Top Handle Bag||Retro Trendy Aviator Sunglasses||Paris Corner Charuto Tobacco Vanille Eau De Parfum Men & Women Spray||Milani Gilded Mini Eyeshadow Palette with 6 Matte & Shimmer Hues – The Wine Down||e.l.f. Glow Reviver Lip Oil, Nourishing Tinted Lip Oil For A High-shine Finish, Infused With Jojoba Oil, Vegan & Cruelty-free, Jam Session||Velvet Scrunchies with Bow and Rubber Bands
1. Denim Shirt Dress: A Timeless, Comfortable Layer
The denim shirt dress is my go-to foundation for this look. It’s casual yet classic, offering a structured base that’s easy to style with other layers. A denim dress is the perfect choice for outdoor vineyard events: it’s comfortable, breathable, and adds a touch of rustic charm that complements the autumnal vineyard setting. The mid-thigh length allows for pairing with tights, boots, or layering with vests and jackets, making it a versatile staple for fall.
2. Oversized V-Neck Knit Sweater Vest: Cozy and On-Trend
An oversized V-neck knit sweater vest is one of fall’s most popular trends, and it brings an extra layer of warmth and texture to this Friendsgiving outfit. The vest adds cozy vibes and creates a chic layered look with the denim dress underneath. With its relaxed fit and classic knit texture, this sweater vest softens the denim’s structure, striking a balance between laid-back and polished. V-neck sweater vests are ideal for vineyard settings where the weather may fluctuate, letting you layer without feeling too bulky.
3. Pattern Tights: A Stylish Pop of Personality
Patterned tights are a simple yet effective way to add personality to an outfit. For this look, I chose a subtle pattern—like tiny polka dots or delicate florals—to give the outfit a unique edge without overwhelming it. Pattern tights not only add visual interest but also provide warmth, making them a great accessory for outdoor fall events. The patterns are a playful touch that pairs well with the classic denim dress and layered knit vest, perfect for a Friendsgiving spent sipping wine.
4. Frye Veronica Booties: Classic, Sturdy, and Comfortable
Frye Veronica Booties are the perfect footwear for a vineyard outing. These leather booties are not only comfortable for a day of walking but also bring a touch of rugged elegance to the outfit. Their slightly worn, vintage look fits right in with the rustic ambiance of a vineyard, while their durability makes them ideal for uneven paths or grassy areas. The slight heel provides height and shape without compromising comfort, which is essential when spending the day on your feet.
5. Oversized Leather Jacket: An Essential Fall Layer with Edge
An oversized leather jacket is a must for cool autumn days, especially when heading outdoors. The leather brings a bit of edge to the outfit, balancing the softness of the knit vest and denim. Its oversized fit keeps the look relaxed, while the rich leather material adds a polished, stylish vibe. Leather jackets are timeless, versatile, and easy to throw on or off as needed, making them perfect for a day at the vineyard.
6. JW PEI Women’s Elise Top Handle Bag: Compact, Chic, and Sustainable
When it comes to bags, the JW PEI Elise Top Handle Bag is both functional and stylish. Its compact size is ideal for vineyard trips, allowing just enough space for essentials without weighing you down. JW PEI is known for its eco-friendly, vegan materials, so this bag is a stylish choice that’s also sustainable. Its structured, top-handle design gives the outfit a polished feel and balances the relaxed vibe of the other pieces.
7. Retro Trendy Aviator Sunglasses: Stylish with a Vintage Touch
Retro aviator sunglasses are a stylish and practical addition to this outfit. Their oversized frames bring a touch of glam, and they’re the perfect accessory for a sunny vineyard day. Aviators are a timeless style that pairs well with the edgy leather jacket and casual denim dress, adding a bit of retro flair to the look.
8. Paris Corner Charuto Tobacco Vanille Eau De Parfum: A Signature Fall Fragrance
To complete the look, I chose Paris Corner Charuto Tobacco Vanille Eau De Parfum, a cozy, warm scent with notes of tobacco and vanilla. This fragrance is perfect for fall vineyard outings, with its spicy, rich aroma that complements the earthy vineyard surroundings. It’s a unisex scent, making it a bold yet sophisticated choice for a day with friends and wine.
9. Milani Gilded Mini Eyeshadow Palette – The Wine Down: Warm Hues for a Wine-Inspired Look
The Milani Gilded Mini Eyeshadow Palette in “The Wine Down” offers the perfect hues for a vineyard trip. With rich, warm tones like burgundy, plum, and shimmery gold, this palette brings out the fall spirit and complements the surrounding vineyard scenery. I used a blend of matte and shimmer shades to create a soft, wine-inspired eye look that adds a subtle glam touch without overpowering the outfit.
10. e.l.f. Glow Reviver Lip Oil in Jam Session: High-Shine, Nourishing Lip Color
No vineyard-ready look is complete without a touch of lip color, and e.l.f.’s Glow Reviver Lip Oil in “Jam Session” is my choice for this Friendsgiving. Infused with jojoba oil, it keeps lips hydrated and adds a high-shine finish that feels fresh and natural. The soft berry tint matches the autumnal color palette and complements the earthy tones of the outfit, adding just enough color to bring the look together.
11. Velvet Scrunchies with Bow: Practical and Pretty
Lastly, a velvet scrunchie with a bow is the ideal hair accessory for this outfit. Velvet adds a luxe feel, and the bow detail is festive and feminine, perfect for a Friendsgiving vibe. It’s functional, too, making it easy to tie up hair if it gets windy outdoors. A small but stylish addition, the scrunchie ties together the cozy, layered look.
Final Thoughts: The Perfect Friendsgiving Vineyard Outfit
From the denim shirt dress to the Frye booties and cozy sweater vest, this outfit strikes the perfect balance of comfort, style, and seasonal charm. The layered textures, earthy tones, and thoughtful accessories make it a well-rounded look for a Friendsgiving vineyard day. Whether you’re posing for photos with friends, savoring wine by the glass, or taking in the autumn views, each piece in this outfit plays a role in creating a look that’s both practical and picturesque.
Tips for Styling Your Own Friendsgiving Vineyard Outfit
- Layer Strategically: Choose pieces that layer easily, like a shirt dress under a vest and a jacket. This approach ensures comfort while letting each item add a unique element to the look.
- Opt for Sturdy, Comfortable Shoes: You’ll likely be walking around outdoors, so pick boots that offer both style and support. A leather boot like the Frye Veronica is perfect for vineyards.
- Add Small Statement Accessories: Sunglasses, a unique bag, or a signature scent can make the outfit feel complete without being overdone. Accessories with texture, like a velvet scrunchie, add a festive touch.
- Choose a Fall-Ready Makeup Palette: Use eyeshadow colors that complement fall scenery—warm hues like plum, burgundy, and gold create a polished look.
A Friendsgiving at a vineyard is the ultimate fall gathering, and the right outfit can make the experience even more memorable. With a blend of cozy layers, chic accessories, and practical pieces, you’ll be ready to enjoy a day of fun, fashion, and friends. Cheers to celebrating the season in style!
Check out what I'm loving right now on Amazon!
