Winery outfits that look fabulous but keep you comfy on your next trip inland.
By now you’ve probably heard of internet sensation Emma Chamberlain’s favorite outfits for when it’s hot outside: a long black skirt, crumpled socks, loafers and a simple white tank top. TikTok is crazy about people with different body types and style aesthetics trying out the fit, and it actually looks good on everyone.
It’s also an incredibly versatile and chic combination that could fit from one context to another, such as going to work or spending the afternoon at a winery. The only problem is that everyone wears it. It’s the internet’s worst kept secret. So if you’re planning a trip to upstate BC or stopping by a Vancouver Island winery, these outfit suggestions will help you stay cool, feel good and look fabulous.
There are practical considerations to visiting a vineyard, you will most likely be walking around so stilettos are not a good idea and there could be mosquitoes or other insects so too much exposed skin could pose a risk. But it’s also going to be hot and you don’t want to be sultry in a long sleeve shirt and jeans. We’ve rounded up some creative solutions to all of these concerns, making sure everything looks effortlessly put together and stylish.
You can’t go wrong with a jumpsuit
I’m not Emma Chamberlain, but my favorite outfit has always been a jumpsuit. I’m a certified lazy girl, so I think an all-in-one instant ensemble is ideal. They also work well in vineyards because there are so many options that are pretty and flattering, but with long, flowy, wide-leg pants to keep you cool and free from bug bites.
Perfectly casual , this Simons style with a bow accent and fun print can be worn alone and accessorized with accessories such as an over the shoulder denim jacket and more formal sunglasses and layered jewelry , or dressed down with a pair of trainers . Normally I would go for white but overall this color is to be avoided in a vineyard as walking will raise fine dust and dirt.
There’s also this jumpsuit from Canadian small business Finding July, which comes in either pink, green or black and is super flattering with the thick high waistband, bow effect at best and keyhole front. And of course Smash + Tess is always an option, but I’d go for the Fresh Jumpsuit for a vineyard, it’s more wearable outside.
Decide on suitable sets
Another option for a simple outfit is a matching set, with either pants or a long skirt. It’s an opportunity to play around with colors and patterns as monochromatic looks are very trendy these days. Each piece can also be mixed and matched with other basics in your closet, so investing in a set pays off when you can make multiple other outfits out of them.
My favorite place for matching kits is Reformation because although they are based in the US, they don’t charge customs and standard shipping is free. This lemon skirt and crop top set is absolutely cute, but the skirt is short. So if you’re worried about bugs, I’d go for this long blue plaid skirt and tank combo (although it’s actually linen) or this yellow striped halter top and button down. Up-skirt set that spreads big Italian summer vibes. That puff sleeve crop top and flowy skirt are gorgeous too, especially with the headscarf.
For the girls who prefer pants, Hillary McMillan has some great options that are also available at The Bay. RW & Co., Old Navy and Bannana Republic also stock matching shirts and pants but do not sell them as sets, which offers the benefit of easy sizing when the top and bottom are different sizes, but it can be difficult to match the products vote if one is sold out online or in store. In some cases it can also be more expensive.
Cottagecore beautifully photographed in a vineyard
Cottagecore dresses were made to walk through fields and a vineyard is close enough. Just like a jumpsuit, a maxi dress can be styled up or down and suits almost any weather, as fall can be unpredictable in the wine country. I have a full list of summer dresses here, but for transitional pieces I would look for heavier fabrics that are looser.
Cottagecore dresses tend to be for the transitional season and you can see a full rundown here.
The Lastest Scoop is one of my favorite places to shop because they always have new seasonal styles and so many of them you can’t find anywhere else (btw, I just bought this shawl top there that was featured in a VIA TikTok recently). . For a vineyard, choose a midi or maxi dress with half sleeves like one of these pink or blue floral wrap dresses. There’s also this beautiful green number with a keyhole back and a small cut-out in the front.
For something a little less girly and floral, I’d opt for this buttoned maxi dress, which can be belted at the waist or styled with a crossbody bag for a street style look. And if that’s too casual, this satin button down shirt dress is the same outfit in a different font.
Every basic look is upgraded with accessories
No matter what you end up wearing, even if it’s a t-shirt and jeans, it can always be styled with jewellery, hats, sunglasses and a fun bag to make it look like a more sophisticated outfit.
The difference between influencers posing on social media and us getting ready in the morning is in the context and the details. They know how to pose and edit to make their outfits look good, but they also spend time on small details like layering different styles of chain necklaces, adding a belt, and cuffing their jeans or sleeves to look more tailored.
Choose durable materials like leather and opt for junkier jewelry if you are going out for a day and could potentially damage your clothes. And invest in well-made pieces that you can wear again and again in different ways and in different scenarios. A two-piece set, jumpsuit or dress is just the basis of the outfit, how you style it determines the end result and can say a lot about your personal style.