10 Easy Ways To Nail Transitional Dressing (Because None Of Us Know What To Wear When It's 65 Degrees)

Transitional dressing — dressing for mediocre weather in between seasons — isn't as easy as it might seem. You head out in a cute dress and light jacket only to find you're absolutely freezing in the office air-con and shivering during your lunchtime walk in the park. Then the next day you throw on a chunky knit sweater and pants only to be sweating when you hop on the subway. Sometimes it can feel totally impossible to nail it when the weather's stuck at an unexciting 65 degrees. So what the heck do you do?


As stylist Olivia Eslami told Today, "(the) overall challenge is to remain comfortable yet stylish during these temperature changes." So you'll want to invest in great pieces that can easily transition from season to season, yet can be styled to keep you cool on those sunny 65-degree days yet warm and dry on those rainy 65-degree days. But, don't fret. If you're ready to transition your wardrobe with more transitional pieces, we've got you covered.

Don a denim jacket

Nashville blogger Michelle Tomczak showed us how it's done on Instagram with this chic look. Tomczak had the idea of draping her denim jacket over her shoulders, which is perfect for 65-degree weather that's not too hot, not too cold. If that's not for you, though, a traditional blue denim jacket goes with pretty much everything, so you don't have to worry about it ruining your look if you keep it on all day.


There are so many different shapes and styles of denim jackets out there that you can totally tailor this look to your personality. Carrie Underwood may be all about denim and rhinestones, but you could go more understated with a plain dark navy look, or you could opt for a lighter blue number. 

But why stop there? You can get your hands on every color of denim from white to pink to even black, so it's a chance to be creative. However, you will want to choose the length wisely on those in-between weather days. Go for something long if it's a breezy 65-degree day, or something cropped if there's a chance of things warming up later on. "I always suggest a slightly oversized style ... as it'll look chic draped over dresses during the summer, but will also allow you to wear jumpers underneath during the colder months," said Farrah-May Archer, leader of the Styling Team at Stitch Fix UK, in an interview with Women and Home.


Change up your look with tights

One of the easiest ways to make a look go from fall to winter — or bring a traditional summer look into the spring — is to add a pair of tights. A good pair of tights will allow you to wear many of your dresses year-round without having to worry about being a little chilly on those in-between days. As stylist Shea Daspin told Marie Claire, you'll probably want to have at least a couple of pairs on hand, depending on which season we're saying goodbye to and what look you're going for. "Winter is great for black opaque tights, but once it starts to warm up, you can slowly opt for tights with a lower denier. The warmer it gets, the more sheer the tights can be," she explained.


Of course, black tights will go with most darker outfits and are also a great way to transition a shorter skirt or dress into another season. If you want to make things a little more fun though, you could easily pair colored tights with one of your summer dresses and a jacket to brighten a gloomy day.

Transition seasons with an oversized look

An oversized button-down shirt is rarely a bad idea, particularly when you're dealing with mediocre weather. One of the reasons a button-down is such a staple is because it's so versatile and cozy at the same time. You can pair something like this with almost anything, and you can stay extra warm by wearing something like a tank top underneath, too!


The oversized look is ideal to rock with a pair of skinny jeans or leggings to balance things out, and you can also wear another jacket over the top of it if you want to. We'd suggest something a little more structured to keep the oversizing to a minimum, which can sometimes look like too much if you don't keep it just to the top or the bottom. It also goes well with a range of footwear, from sneakers to boots to heels, which means you can tailor it to what you need that day.

Midi skirts are ideal for middle-of-the-road weather

Midi-skirts are a fab option for those not hot but not cold days. Here, Switzerland-based Instagram user Ivana Kovačević shows us how it's done with a long denim skirt (which is totally making a comeback, by the way!) and boots. The slit through the middle of the skirt keeps the look from being too wintery but makes it a perfect go-to for spring-to-summer and summer-to-autumn transitions. 


You don't have to have a high slit in your look though, as a closed midi skirt would be just as useful. If you don't want to do denim (maybe you're already wearing a denim jacket and aren't a double denim fan) you can change it up with a skirt made of another material, like satin.

Kovačević's style shines in the way she matched the knee-high boots to her trench, which can both be great staples for those transitioning weather days, and she kept the look cute but simple by pairing the dark denim skirt with a simple white top and brown belt.

Go long in a cardigan

Long cardigans are a great choice for those in-between weather days, as they'll keep you nice and cozy without being too warm. They make a great accessory to any outfit since they come in so many colors, so you don't have to worry about any clashing. This stunning teal number worn by Instagram user @workingmamastyle proves just that, as she paired the colorful outerwear with an all-white look. You could turn that totally on its head if you're someone with a wardrobe full of black, using a cardigan as a pop of color. 


There are no rules about what kind of outfit you can pair a long cardigan with, either. The pieces go great with a pair of jeans, and, depending on if you run hot or cold, you may prefer to pair the cardigan with a short-sleeved t-shirt or a long-sleeved top (especially if you know you're going to be outside a lot). You can also wear the cardigan with a dress, long or cropped pants, and everything in between, as well as pretty much any kind of footwear, including boots.

Reign supreme with a transitional rain jacket

When you're going from season to season, a good rain jacket could be a godsend to keep you cozy and dry. "For the colder months, opt for one lined in fabric to keep you warm in the cold winter rain, but once April hits, you can get away with unlined versions as well," Shea Daspin told Marie Claire of the outerwear. If you can, try opting for one with removable lining so it can be a little more versatile no matter what season you're heading into. 


One thing to remember is that rain jackets don't all have to be boring, practical-looking pieces. As you can see from Instagram influencer Teressa Kralova's look (above), they can be super fun too! A metallic number like hers can add a lot of fun to a rainy-day outfit (or at least one where it looks like the clouds could burst at any second) and will keep you that much warmer and drier at the same time.

Lace up your boots

We'll be honest, no matter what the season, we just can't get enough of boots. If you have a good pair of boots, you'll be able to nail so many transitional dressing looks with no problem. We'd recommend investing in a black pair that you can match with pretty much anything, as black boots will go with pants, all colors of jeans, dresses, skirts, and almost everything in between. They'll also help you stay dry on those rainy in-between days and never look out of place when you're dealing with 65-degree weather. 


If you're a fan of a dress, you may want to invest in a more neutral color boot too, like nude or a brown, as it'll probably be easier to pair with more summery-looking or neutral ensembles without being too jarring. "Boots are always a wardrobe staple but the ankle boot, (C)helsea boot-length styling always look(s) great with dresses, skirts and jeans," personal stylist Nina Whitehead wrote of the transitional must-have on her blog, Edits.

Invest in great t-shirts

A quality T-shirt can serve as a go-to in any season since it offers you the chance to build over the top of it and layer — which is exactly what you want in a transitional outfit. As celebrity stylist Micaela Erlanger told Byrdie, you'll want to take your time when it comes to T-shirt shopping to make sure you get something that's the right fit for you, and good quality so you can wear it time and time again. 


If you can, try investing in a couple of different fits and colors so you can keep on wearing your pieces throughout the year. A white T-shirt never goes out of style and is perfect with pants or skirts (or even shorts if you're feeling brave in 65 degrees!), while you may also want to have a black T-shirt on hand to go under darker cardigans, blazers, or sweaters.

Of course, T-shirts come in all sorts of shapes and sizes, from cropped to oversized, so having a few different options on hand will mean you'll be able to rock all kinds of looks on those mediocre weather days while still adhering to your own personal style. There is a range of different ways you can style an oversized shirt, while a more fitted, basic T-shirt could even go underneath a dress.


Go back to black jeans

Trust us when we say you just can't go wrong with black jeans, especially when you're dressing for in-between seasons. One of the best things about the darker denim look is that it's hard for these pants to look out of place, no matter where you're going or what you're doing. Dressing up for a night out? Pair them with a nice top and a blazer with sandals, fancy flats, boots, or heels. Going somewhere more casual during the day? Rock them with a sweatshirt, boots, or sneakers. Trust us, you need black jeans in your life.


"Black jeans are a staple in everyone's wardrobe, whatever the season and whatever the occasion," stylist ambassador at Stitch Fix, Katie Eastwood, told Good To Know. "They act as the perfect base layer from which you can build an array of outfits, whether it be for a casual weekend walk with friends, a date night or an all-important interview." That means they're ideal for transitional dressing, as you can build the rest of your outfit around them. 

Just make sure you look into our very favorite sustainable denim brands before you treat your wardrobe to any new denim numbers.

Blaze a transitional fashion trail in a blazer

Blazers are ideal transitional wear because you can pair them with so many things — and they're ideal for layering too. Though blazers have a bit of a reputation for being more formal and often too structured for some occasions, in reality, they can be dressed down with things like blue jeans and sneakers. They're also ideal for situations where you may need a rain jacket but still want to look presentable when you're inside, as you can find many blazers thin enough to be worn under other coats or jackets. Likewise, there's a whole range of lengths, which means you could opt for a longer one to wear with tighter pants or leggings or a cropped version with pants or a dress.


"If I were to style [a] blazer for fall and winter, I would pair it with a cashmere turtleneck, a pair of flowy wool pants, a long necklace and booties. This look will take you everywhere," shopper Barb Heffernan told Nordstrom. "For spring and summer, I would do a more casual look with a pair of jeans, a T-shirt, some gold hoops, and either wedge sandals or cool sneakers depending on what your plans are," they added. Celebrity stylist Micaela Erlanger is also a big fan. "I live in T-shirts and blazers. For me, it's a T-shirt bra, a T-shirt or blouse, and then a blazer to complete the look," she told Byrdie.