Let me start by admitting that I’m a California girl, which means I can pretty much get away with skirts and dresses year-round without much trouble. However, there are some really great options for those of you who have much colder weather to deal with than I do.
Tights, But Not Like You Think
Okay, so while this might be the most obvious of the options you have to keep warm when the weather gets colder, it’s possibly the most versatile. Rachel’s sequined dress shows that it can easily be made festive, which is perfect as the holidays get closer.
If you don’t think that a normal pair of tights will be enough, buy pairs that are more opaque as they will be made of thicker material. If at this point you’re scoffing and thinking, “You’ve never been to x,” then try thermal tights. Thermal tights have the potential to be even warmer than pants!
Thermal tights have the potential to be even warmer than pants!
If you prefer the look of sheer tights, there’s a solution for that too. Get a pair of thermal tights that matches your skin tone. (This doesn’t have to be a perfect match, just close enough). Then layer the sheerer pair of black tights over them, and you shouldn’t be able to tell you have thermal tights on underneath. Magic! Still not warm enough? Add long stockings over the thermal tights and sheer black tights. If you utilize this trick, you should be able to get away with wearing skirts and dresses even when it’s freezing out.
Knee-High Boots and Socks
One way to stay warm as you transition into the new season, and incorporate a fall staple while you’re at it, is to wear leather knee-high boots or riding boots. Leather boots will last you forever, so they’re a really good piece to invest in. A really beautiful pair that would definitely be a splurge, but is a good choice if you’re looking to invest, is the Gia tall boot from Loeffler Randall.
This look pairs perfectly with a dress in a seasonal fabric like flannel. Kiel James Patrick is selling the dress Sarah Patrick was wearing again this year; it’s a fall classic for their brand. And for good reason, it’s super cute!
Because flannel is a pretty heavy fabric it should help to keep you warm, but if needed, you can easily throw a coat or a sweater over it as well. Depending on the weather in your area, the boots alone might be enough, but long socks like Sarah has on are the perfect way to add some extra warmth. This look, to me, just screams fall, even if you aren’t blessed with a beautiful New England backdrop like she is.
A Coat Can Make Any Dress Warmer
How cute is this look Emily Jackson and her little girls wore to her sister’s wedding in the fall? Dresses are pretty standard for weddings, so the perfect way to keep warm at a fall or winter wedding is throwing on a coat before you go out the door. If you’re going to church or doing anything more formal, heels work perfectly.
The wrap style is an easy way to accentuate your waist.
If you want to have a look along the lines of what Kate Middleton might wear, then choose a longer coat over a shorter one. It can be the same length or even longer than the dress you’re wearing underneath. The blush color Emily wore is beautiful, and lighter neutrals can help the colder months feel less dreary. The wrap style is also an easy way to accentuate the waist. It’s an easy way to look more feminine in a sea of black coats!
Wear a Longer Dress or Skirt
There’s no reason why you should have to give up skirts and dresses when the seasons change. But, it’s still time to put away that sundress. A big part of dressing in a ladylike way is that your clothing has to fit the environment, the season, and the weather. By choosing a longer dress, it will be more seasonally appropriate, and, if you pick a heavy fabric, it will even help to keep you warm. Another aspect of dressing to fit your environment is the level of formality for what you’re doing. You can easily keep it more casual with a pair of booties or ballet flats. To dress it up, a pair of heels works perfectly.
One plus with longer dresses and skirts is that you don’t have to be as worried about what’s showing when sitting down, bending over, or the wind blows (heaven forbid!). Today, many women complain about having a hard time finding longer dresses and skirts that are still fashionable and modern. Trust me, I feel the struggle! Nobody likes to walk around the mall all day and come back having found nothing. I tend to have luck in stores like Anthropologie and Nordstrom (specifically the Rachel Parcell clothing line).
The sweater dress is truly a fall item. When you find one that fits you right, compliments are a guarantee! You can find them really easily at many stores this time of year at all different price points. They’re a great choice especially in 2020 because they come across as more casual than a lot of other dresses or skirts do, so they’re easier to wear to functions where you think you’d stick out like a sore thumb in a dress if everyone else were wearing pants. Plus, they’re honestly just as comfortable as sweats for your work from home days.
Accessorize the sweater dress with a scarf or a felt hat to make it even more seasonal.
You can accessorize the dress with a scarf or a felt hat to make it even more seasonal. If you buy one dress and find you enjoy wearing it, you can buy them in different colors, cuts (turtleneck versus crewneck) and textures (ribbed versus cable) to wear this look more often.
Add a Layer Underneath
One way to transition some of your dresses into fall is to add a long-sleeved shirt underneath. This will help on some chilly nights when the temperature drops and will let you ease into fall. Amber’s outfit was perfect for wearing in the Swiss Alps, especially coupled with her fishtail milkmaid braids, but the concept is surprisingly versatile, and you can create some very different looks.
It’s the kind of thing you would have seen Rachel Green wear on Friends, and as a result of a resurgence of its popularity in recent years, a lot of ‘90s trends are still in style today. And just think how perfect an overalls dress with a sweater or long-sleeved shirt underneath and some cute combat boots would be for a trip to the pumpkin patch.
Yes, You Can Wear Skirts and Dresses with Rainboots
Pairing a dress or skirt with rainboots is such a fun outfit in my eyes. It feels very freeing and like you’re ready to have some fun in the rain. So rather than begrudgingly accepting the poor weather, as I think a lot of us often do, make it a bit more fun with a fabulous skirt over the rainboots instead of a pair of jeans.
Pairing a dress with rainboots is very freeing — like you’re ready to have some fun in the rain!
And if you’re willing to take it up a notch, colored rainboots are always a fun choice. I bought a green pair last year and was surprised at how much use I got out of them. And it hardly ever rains in southern California! So if you live somewhere where it does, there’s no way you could go wrong with this.
When we think of fall outfits, we tend to think of sweaters and scarves paired with jeans or leggings. This is really popular, as the way people dress has shifted to be much more casual. But, if you think outside the box a bit, you’ll find that there are actually a ton of options for wearing dresses and skirts in the fall and winter that don’t require you to freeze to death or to look ridiculous. Choose the right skirts, dresses, and accessories, and you won’t have to wear pants all fall if you don’t want to.