winter sweater with summer dress

Get the Most Out of Your Wardrobe All Year Long by Pairing Different Seasonal Clothing Together

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Are you struggling to find creative ways to style your clothes? I’ll let you in on a little secret. Psst, come closer. The secret? Pair your different seasonal clothing together. Mixing your summer clothes with your winter clothes or your spring pieces with your fall pieces is not a mistake, but a really smart fashion move. Not only do you get to fully maximize your wardrobe all year long, but mixing and matching this way allows you to create some super stylish and fashion-forward looks. Get ready to update your wardrobe by learning how to pair different seasonal clothing together!

Understanding Seasonal Colors

Though soon you’ll discover that you may be able to mix and match more than you thought, it’s worth noting that some wardrobe pieces are best left in their respective season. Specifically clothes with colors that are highly associated with certain seasons.

Whew, that’s a mouthful.

For instance, in fall, we tend to see earthy tones such as rust, brown, and forest green. In contrast, during summer, we see brighter hues such as hot pink, sky blue, and yellow.

When pairing seasonal clothing together, it’s a good idea to keep the seasonal colors in mind. You can mix and match different colors, but they should still feel cohesive with your season. For example, black is a year-round color and can be worn in every season, but a complete outfit of chocolate brown, plum, and rust would look a little out of place in the summer.

Rules are made to be broken (so why even mention them at all, I get it), but it’s helpful to know that first!

Okay, now for ways you can actually and realistically pair your different seasonal clothing together.

1. Pair a Chunky Sweater With a Flowy Summer Dress

winter sweater with summer dress

sweater | dress | shoes | sunglasses

The contrast of the winter sweater in a chunky texture with the lightness of the summer dress creates a visually appealing look that is both stylish and practical!

Though this look is a chic home run, something to consider is the length of the sweater. If the sweater is too short, it can make the outfit look choppy and unpolished. If the sweater is too long, it can make you look frumpy.

One of the best solutions is to belt your dress and tuck the sweater underneath it, like so! This will create a flattering look and a balanced silhouette with the dress.

2. Layer a Denim Jacket Over a Summer Dress or Lightweight T-Shirt

denim jacket with white dress

jacket | dress | shoes | earrings

A denim jacket, traditionally thought of as a fall wardrobe item, is really a timeless piece that can be worn year-round. Denim jackets are great because not only do they add a casual, cool vibe to any outfit, but they are perfect for adding an extra layer of warmth during those transitional months.

For a casual and comfortable look, pair your denim jacket with a flowy summer dress. The denim jacket will add structure to the dress while also keeping you warm if the weather turns chilly.

If you prefer a more laid-back outfit, try layering your denim jacket over a lightweight t-shirt. This is a great option for those in-between weather days when it’s not too hot or too cold. For a chic and effortless look, tuck your t-shirt into a high-waisted pair of jeans and pair it with your favorite sneakers or flats.

3. Wear a Turtleneck With Shorts or a Mini Skirt

striped turtleneck with shorts

turtleneck | shorts | loafers | bag

When we think of turtlenecks, we often imagine them paired with jeans or pants during the colder months. But have you thought about pairing turtlenecks with shorts or mini skirts for a unique and fashionable look?

To pull off this look, choose a lightweight turtleneck in a neutral color such as black, white, or gray. Then choose shorts for a polished look or a mini skirt for a fun and flirty vibe. Not only is this a stylish and unexpected way to wear a turtleneck, but it also allows you to wear your favorite summer pieces even when the weather starts to cool down. And you can wear your favorite winter pieces even when the weather starts to rise!

By the way, do you know the best winter and summer pieces you should have in your wardrobe? Do you need help getting the right clothes? I created a resource for you that will help you build your dream wardrobe from scratch – beginning to end!

4. Pair Ankle Boots With a Summer Dress or Shorts

ankle boots with summer dress

dress | boots | belt

One of the best ways to add a touch of style and edge to your summer dress is by pairing it with ankle boots. This is a great way to give your summer dresses a different feel, even allowing you to transition your wardrobe between seasons seamlessly when that time comes.

Ankle boots and shorts also make a great combination. This look is perfect for those with a casual edgy “tough girl” aesthetic. And even if that’s not you, come early autumn days, this look is perfect for when it’s still warm enough to wear shorts but you need to cover your feet.

5. Pair a Faux Fur Coat With a Slip Dress and Heeled Sandals

faux fur coat with slip dress

coat | dress | shoes | earrings

If you’re looking for a way to elevate your winter wardrobe, a faux fur coat is a must-have item. Not only is it incredibly warm, but it also adds a touch of glamour to any outfit. To make the most out of this statement piece, pair it with your summer slip dress and strappy-heeled sandals.

The contrast between the heavy coat, the delicate dress, and the open-toed shoes creates a balanced and stylish look. Plus, the heeled sandals will add some height and elongate your legs, giving you a sleek and polished appearance!

6. Pair a Denim Shirt With White Linen Pants

denim shirt with linen pants

shirt | pants | shoes | earrings

Pairing a denim shirt with white linen pants is an excellent choice! The mix of textures is perfect for the spring and summer months. It’s easy to create this look too. First, choose a classic blue denim shirt and pair it with white linen pants. Easy peasy! For shoes, keep it simple with some sandals or espadrilles, or dress it up with some wedges or heels.

For cooler weather, layer the outfit with a cardigan or blazer. The denim and linen pairing also works well with a leather jacket. You can also switch up the look by tucking in the shirt.

7. Wear a Leather Jacket With a Sundress

leather jacket with sundress

jacket | dress | shoes | hat

Who says leather jackets are only for the fall and winter seasons? Leather jackets can add a cool, edgy vibe to any outfit – including a sundress! This unexpected pairing creates a fun, unique look that is perfect for running errands, date night, or transitional weather.

When selecting a leather jacket to wear with a sundress, opt for a fitted or cropped style to balance out the flowy silhouette of the dress. For a classic look, pair a black leather jacket with a floral sundress and sneakers. Alternatively, you can easily dress up this ensemble with strappy sandals.

Related: 14 Ways to Expand Your Wardrobe on a Tight Budget

8. Pair a Wool Coat With a Cropped Top

wool coat with button down

coat | top | pants | shoes

It might seem like an unusual combination, but pairing a wool coat with a crop top can create a stylish and trendy outfit. To make this pairing work, start by selecting a crop top that is appropriate for the season. For cooler temperatures, choose a long-sleeved or knit crop top that will provide some coverage.

When selecting a wool coat to wear with your crop top, look for a coat that is midi or maxi length. This will create a more balanced silhouette and flattering shape. To complete your outfit, pair your wool coat and crop top with high-waisted pants or a skirt. This will create a more cohesive look and ensure that you don’t show too much skin, giving your outfit a chic appeal.

9. Wear a Cashmere Sweater With Linen Pants

cashmere sweater with linen pants

sweater | pants | shoes | bag

When it comes to combining seasonal clothing, it’s important to focus on fabric as well as color. The cozy comfort of cashmere is perfect for colder months, and pairing it with lightweight linen pants creates an interesting contrast that elevates the look.

A cashmere sweater is a timeless classic. Linen pants, on the other hand, are breathable and light, perfect for warmer seasons. However, by pairing them with a cashmere sweater, they can be transformed into an all-season staple! Opt for neutral colors like black, beige, or navy for a more sophisticated look.

10. Pair a Wool Coat With a Summer Mini Dress and Knee-High Boots

wool coat with summer dress

coat | dress | boots

A wool coat is a must-have in any winter wardrobe. It’s warm, versatile, and instantly adds a chic touch. When paired with a spring/summer mini dress, the look becomes flirty and feminine.

Knee-high boots are the perfect footwear for this outfit. They add a touch of sophistication and elegance, while also keeping your legs covered and warm. Pairing a wool coat with a mini dress and knee-high boots is a classic outfit that can be worn for various occasions, from a holiday party to a day out shopping. Though I’m partial to a neutral wool coat, experiment with different dress and coat colors to make it your own!

11. Pair a Tweed Blazer/Jacket with a Tennis Skirt

tweed blazer with tennis skirt

jacket | skirt | shoes | earrings

One perfect example of pairing your different seasonal clothing together is by pairing a tweed blazer with a tennis skirt. This combination blends the classic fall sophistication of a tweed blazer with the playful summer style of a tennis skirt.

For this look, opt for a tweed blazer that has neutral tones like black, white, or beige. These colors can easily pair with different tennis skirts and allow for versatility in styling. Look for a blazer that fits well, has a tailored silhouette, and is made of high-quality materials.

When it comes to the tennis skirt, choose a length that flatters your body type. A mini skirt can add a youthful vibe while a knee-length skirt can create a more polished look. When pairing a tweed blazer with a tennis skirt, you are mixing classic with sporty, and the outcome is effortlessly chic!

12. Wear a Wool or Knit Maxi Skirt With a Tank Top

wool skirt and tank top

skirt | top | shoes | necklace

When styled right, a wool maxi skirt can be a great piece for warmer seasons as well. Not only does it provide ample coverage, but it also adds a touch of elegance and sophistication to your outfit.

One of the easiest ways to wear a wool maxi skirt is by pairing it with a simple tank top. This creates a balanced and effortless look that’s perfect for running errands or going on casual outings. When it comes to shoes, sneakers or sandals are the best options for this casual summer look!

13. Wear a Cardigan Over a Tank Top and Shorts

cardigan with tank top and shorts

cardigan | top | shorts | sneakers | hat

As the temperatures start to cool down in the fall, it can be tempting to pack away your favorite summer clothes. But, with a few smart pairings, you can still rock your shorts and tank tops well into the fall season!

One of our favorite ways to transition summer pieces into fall is by layering a cozy cardigan over a tank top and shorts. This combination is perfect for those days when the sun is still shining, but there’s a chill in the air.

To pull off this look, start with a basic tank top and a pair of denim or tailored shorts. Choose a lightweight, neutral-colored cardigan in a fabric like cashmere or cotton. The cardigan should be long enough to cover your hips and add a bit of warmth to your outfit.

This outfit is perfect for a casual brunch with friends or a day spent running errands. It’s also versatile enough to transition from day to night. Just swap out the shorts for a pair of slim jeans and add some heels for a chic evening look.

14. Pair Tights With Shorts

tights with shorts

tights | shorts | blazer | shoes | earrings

Don’t pack away your favorite shorts just because the weather is getting chilly. With a simple pair of tights, you can keep your legs warm while still showing off your summer wardrobe. Not only is this an easy way to transition into the cooler months, but it’s also a fashionable one!

When it comes to color, black tights are a safe and classic choice that will pair well with most shorts. However, don’t be afraid to mix it up and experiment with different colored tights, just say no to nude. To complete the look, pair your tights and shorts with shoes in the same color. This will help elongate your legs and create a polished, put-together look.

15. Wear a Long-Sleeve Shirt Under a Dress

long sleeve shirt under dress

shirt | dress | shoes

If you have a sleeveless dress that you love but it’s not quite appropriate for the cooler weather, layering a long-sleeve shirt underneath can make all the difference! To make sure the outfit looks intentional, choose a dress with spaghetti straps. A fitted shirt or a turtleneck underneath works well for a sleek and sophisticated look, while a more relaxed shirt can add a casual vibe.

This trick works well for transitioning dresses from summer to fall, but it can also be applied to spring dresses on a cool day. Try out different combinations to make the most out of your favorite dresses all year round!

How To Organize Your Wardrobe To Best Pair Different Seasonal Clothing Together

If you’re someone who likes to have all your clothes available to you year-round or at least have the option to dip into your off-season wardrobe, you may find yourself struggling with closet space. Don’t worry – with some strategic organizing, you can have it all. Here are some tips:

  • Keep your off-season clothes in an extra guest closet. This way they don’t take up extra room in your closet, but they’re nearby if you want them.
  • Divide your closet into sections by season. This way, you’ll be able to quickly identify what clothes you have available for the current season.
  • Use space-saving techniques, like stackable bins or storage bags to store your off-season clothes. Make sure the bins are clear and labeled, so you can see at a glance if you want to use the clothes or not.
  • Rotate your clothes regularly to make sure everything gets equal use. This also gives you a chance to re-evaluate if you still love certain pieces or if they’re ready to be donated.
  • Invest in closet organizers like shelves or hanging organizers to make use of every inch of space.
  • Store away all the color-specific clothing and keep the versatile seasonal pieces on a clothing rack for easy access.

Pairing different seasonal clothing together not only helps you create new and exciting outfits but also allows you to maximize and love your wardrobe. With a little bit of creativity, you can create versatile and stylish outfits all year round, while making use of pieces that might have otherwise been sitting in storage!

To make the best use of your wardrobe, organization is key. Up Next: How to Clean and Organize Your Closet Like a Pro


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.