Is there anything more stylish than a chic fall outfit for a day of wine tasting? 🍇🍂
The short answer is “no,” and these outfit ideas will have you looking fabulous as you sip your way through the season.
Chances are, you’re here because you want to dress perfectly for a wine-tasting adventure, and it can be tricky to strike the right balance between chic and comfy.
You want to look stylish, but you also need an outfit that allows you to fully enjoy your day.
Finding that perfect mix of cozy and fashionable for a winery trip is key.
From layered knits to chic boots and cozy scarves, fall offers endless opportunities for creating the ideal ensemble for a winery outing.
These 30+ outfit ideas are here to inspire you to create the perfect look, whether you’re visiting an upscale vineyard or enjoying a casual day out.
Let’s dive into these chic fall winery outfit ideas and get ready to sip in style!
30+ Chic Fall Winery Outfits for a Day of Wine Tasting!
1. Cozy Sweaters & Jeans
A chunky, oversized sweater paired with classic blue jeans is a timeless combo. The sweater gives off a warm, relaxed vibe, while the jeans keep things casual yet chic. Finish the look with some ankle boots for added flair.
Style Tip: Go for a sweater in earthy tones like mustard, burnt orange, or deep burgundy to embrace the fall palette.
2. Maxi Dress & Leather Jacket
For those who want to add a touch of edge to their wine-tasting outfit, a flowy maxi dress with a leather jacket is a great choice. The contrast between the soft, feminine silhouette and the tough leather makes for a bold look.
Style Tip: Opt for deep jewel tones like emerald green or plum for a rich fall aesthetic.
3. Plaid Shirt & Skirt Combo
Plaid is practically synonymous with fall, so why not incorporate it into your winery outfit? A classic plaid shirt tucked into a skirt is the perfect mix of laid-back and stylish.
Style Tip: Pair with knee-high boots for a polished touch or keep it more relaxed with some ankle boots.
4. Cardigans & Boots
Layering is key when the weather’s unpredictable. A long cardigan over a simple dress or top and jeans offers the warmth you need without compromising style. Add some chic boots to elevate the outfit.
Style Tip: Go for neutral tones like beige, gray, or camel to stay cozy and chic.
5. Denim Jacket & Midi Skirt
A denim jacket is a versatile piece that can be worn with almost anything, and it pairs perfectly with a midi skirt for a wine-tasting outing. Add a cute top underneath to complete the look.
Style Tip: Floral prints or plaid can keep your look feminine and playful.
6. Chunky Knit & Leggings
When the weather gets crisp, a chunky knit sweater and leggings will keep you comfy while still looking polished. It’s the perfect blend of cozy and chic, especially when paired with tall boots.
Style Tip: Play with textures like a ribbed knit or cable knit for added dimension.
7. Turtleneck & Puffer Vest
For days that are extra chilly, layer a fitted turtleneck with a puffer vest. This combination provides warmth without sacrificing your style. Pair with a cozy scarf and a pair of jeans for a streamlined look.
Style Tip: Stick to classic colors like black or gray for a timeless fall outfit.
8. Sweater Dress & Over-the-Knee Boots
A sweater dress is a great way to stay warm and still look chic. Pair it with over-the-knee boots for a little added drama, and you’re set for a day at the winery.
Style Tip: Go for a sweater dress in soft, neutral hues, or opt for stripes for a more playful look.
9. Flannel Shirt & Corduroy Pants
For a more rustic feel, you can’t go wrong with a flannel shirt and corduroy pants. This is an easy, comfortable combo for any wine-tasting adventure.
Style Tip: Mix and match plaid colors or opt for a classic checkered pattern to keep things fun and on-trend.
10. Leather Skirt & Knit Sweater
Combine a sleek leather skirt with a cozy knit sweater for an effortlessly cool vibe. This outfit works well for both casual and semi-formal wine-tasting events.
Style Tip: Opt for a skirt in black or rich brown for a more fall-inspired feel.
11. Shacket & Skinny Jeans
Shackets (shirt-jackets) are perfect for fall, offering the right balance of warmth and style. Pair it with some skinny jeans and booties, and you’ve got the perfect winery look.
Style Tip: Go for a plaid or houndstooth print to add a little extra fall charm.
12. V-neck Sweater & Wide-Legged Pants
Wide-legged pants are having a moment, and pairing them with a simple V-neck sweater makes for a sophisticated yet comfortable ensemble for your day of wine tasting.
Style Tip: Choose a sweater in a soft, neutral tone like cream or taupe to complement the flowy pants.
13. Boho Tunic & Leather Boots
A bohemian-inspired tunic dress paired with leather boots is perfect for a relaxed wine-tasting outing. Add a wide-brimmed hat for a bit of extra flair.
Style Tip: Earthy tones like rust, burnt orange, and deep browns will keep you feeling fall-ready.
14. Puffer Coat & Slim Fit Pants
For those colder days, throw on a puffer coat over a cozy sweater and pair with slim-fit pants. This combination offers warmth while still keeping you looking sharp.
Style Tip: Choose a puffer in a rich color like olive or burgundy for a chic fall look.
15. Tweed Blazer & Skinny Jeans
Add a touch of sophistication with a tweed blazer. This timeless piece can be dressed up or down and makes for an elegant winery look.
Style Tip: Stick with autumn-inspired hues like brown, gray, or navy for a polished vibe.
16. Chunky Knit Cardigan & Booties
Pair a chunky knit cardigan with fitted pants and stylish booties for a comfortable, laid-back winery look. This outfit is ideal for those crisp fall afternoons.
Style Tip: A cardigan in mustard or deep red is perfect for capturing the essence of fall.
17. Faux Fur Vest & Jeans
Faux fur vests are perfect for adding texture and warmth to your winery look. Layer it over a simple top or sweater and pair with your favorite jeans.
Style Tip: Pair this look with booties or ankle boots to keep things chic yet comfortable.
18. Wool Coat & Wool Scarf
A wool coat paired with a wool scarf is the ultimate chic look for fall. This stylish combo will keep you warm without compromising on elegance.
Style Tip: Keep the palette neutral for a timeless and versatile fall look.
19. Chunky Sweater & Leather Pants
For those who like to make a statement, a chunky sweater paired with sleek leather pants is a bold but chic choice for wine tasting.
Style Tip: Opt for earth-toned leather for a rich, fall-inspired look.
20. Midi Dress & Cardigan
A midi dress in a deep fall color like burgundy or mustard paired with a cardigan gives you the perfect blend of warmth and femininity.
Style Tip: Complete this look with tall boots and a wide-brimmed hat.
21. Utility Jacket & Plaid Scarf
A utility jacket is an ideal fall layering piece, and when paired with a cozy plaid scarf, it gives off a casual, vineyard-ready vibe.
Style Tip: Choose muted tones like olive or charcoal to keep the look earthy and refined.
22. Cowl Neck Sweater & A-line Skirt
A cowl-neck sweater paired with a flowy A-line skirt creates a lovely balance between cozy and chic. Add tights and ankle boots for extra warmth.
Style Tip: Opt for a sweater in a chunky knit to add texture to the outfit.
23. Jumpsuit & Boots
For a one-and-done look, a jumpsuit paired with sleek boots is a stylish option for wine tasting. Add a wide-brimmed hat to complete the ensemble.
Style Tip: A solid-colored jumpsuit in earthy tones like brown or green will complement the fall season.
24. Tunic & Leather Leggings
A flowy tunic paired with leather leggings strikes the perfect balance between comfort and chic. Add your favorite pair of boots to round out the look.
Style Tip: A tunic in a rich burgundy or rust shade will capture the essence of fall.
25. Trench Coat & Turtleneck
A classic trench coat layered over a fitted turtleneck gives you a polished, sophisticated look perfect for a fall day at the winery.
Style Tip: Go for a timeless camel trench paired with black jeans for an effortlessly stylish look.
26. Knitted Poncho & Jeans
A knitted poncho is the perfect statement piece for a cozy winery day. Pair it with jeans and knee-high boots for a stylish and warm ensemble.
Style Tip: Keep the poncho neutral or go for soft autumn hues for a seasonal look.
27. Bohemian Dress & Ankle Boots
A flowy, bohemian-inspired dress is always a great choice for a day of wine tasting. Pair with ankle boots and minimal accessories for a relaxed yet stylish look.
Style Tip: Opt for a dress with floral prints or in deep fall colors like olive or wine.
28. Cashmere Sweater & Pleated Skirt
A luxurious cashmere sweater paired with a pleated skirt is a stylish choice for any winery outing. Add some ballet flats or boots for a chic finish.
Style Tip: Stick to warm neutrals to create a versatile, elegant fall outfit.
29. Over-sized Scarf & Jeans
An oversized scarf adds
instant style and warmth to any fall outfit. Pair it with a simple top, jeans, and boots for a chic yet cozy winery look.
Style Tip: Choose a plaid or checkered scarf to add a touch of pattern to the outfit.
30. Leather Jacket & Midi Dress
For a more edgy, trendy look, pair a classic leather jacket with a feminine midi dress. The mix of tough and soft elements creates a striking, chic ensemble.
Style Tip: Choose a midi dress in a floral print or deep hues like black or dark green to create contrast.
This Post Is All About 30+ Chic Fall Winery Outfits for a Day of Wine Tasting!