How To Wear The Popular Fashion Trend: Matching Sets (Over 40 & 50)

How To Wear Matching Sets

If you are like me, one of the most frustrating parts of getting dressed is… finding something to go with the skirt/pants/jeans you put on. Putting separates together is definitely trickier than a one-and-done piece like a dress or jumpsuit. But, there is a REALLY simple way to nail separates and look amazing… wear matching sets!  Not only are matching sets very on-trend right now in fashion, but they’re also simple, slimming, and sophisticated. Are you on board with this fashion trend? I’m the biggest fan. Sharing 5 different matching set options ranging from office looks to beach-ready looks. And…make sure you scroll to the very end for some key tips when it comes to matching sets.

Matching Sets

Cropped Blazer and Side Button Shorts

I instantly fell in love with the stunning cobalt blue color of this matching short and blazer set from Alice & Olivia the moment I saw it. This brilliant blue looks so amazing on most skin tones! It’s made of a linen and cotton blend so it’s lightweight for summer. You can wear each of these pieces separately but together they really pack quite the punch. The shorts are high-rise, have functioning gold buttons, and have about a 3″ inseam. The cropped blazer has an open front, notch lapels, and the same matching gold buttons on the cuff as you see on the shorts. To complete the look, I’m wearing a Generation Love tank with a pretty gold link detail at the neck, some pearl hoops, and a pair of Valentino Rockstud espadrille wedges. I’ll wear this matching set all summer long both together and by styling the pieces separately.

Meet Melissa!

For this next look, I wanted to (once again) introduce you to my sweet friend, Melissa Meyers, from The Glow Girl! We exchanged DM’s for a while a couple of years ago and then decided to meet in person during one of my visits to Malibu. I loved meeting her! She definitely a girl’s girl and happy to share ideas, resources, etc. That is actually quite rare in this space. She is a New Yorker, which I SO appreciate because it also means she’s a straight-shooter like me. A couple of other things we share in common: our TV backgrounds and our love for clean beauty. You can check out Melissa’s website here.  And, follow her on Instagram here. You can also see more of Melissa’s amazing style in this post where she shares some of her favorite comfortable flats, this post with a NYC chic look, and this post with some gorgeous office outfits.

Monochromatic Linen Blazer and Shorts Set

Melissa is wearing a super chic monochromatic white/off-white look that’s perfect for summer. Notice how she varies the textures and tones to make the look even more elegant and sophisticated. She’s wearing a lightweight ecru boyfriend blazer with linen shorts and a classic white tee. She lengthened her legs by wearing a super cool pair of skin-colored braided heeled sandals. I love how she chose a blazer and then grabbed a pair of shorts that coordinate. It looks like a set she bought together, but she just grabbed the pieces out of her closet. So… monochromatic matching sets don’t need to match perfectly to achieve this cool girl look.

Boyfriend Blazer & Matching Shorts Set

These next images were actually taken the very first time I met Melissa back in Malibu in 2021. Melissa is wearing the same set featured above with a few accessory swaps! We wanted to show you just how versatile matching sets can be. When you invest in quality basics like any of these sets, they will stand the test of time, season to season.

I’m wearing a boyfriend blazer and matching shorts by Alice + Olivia but this time in a gorgeous poppy color. Boyfriend blazers are still very on-trend. You might remember this blazer from this post talking about how to wear a boyfriend blazer. It’s still one I reach for each summer because it’s SO gorgeous! The bold color is such a beautiful addition to your wardrobe. And I love the relaxed fit. I paired it with the matching Alice + Olivia shorts, a basic white tee, and white braided heels. These shorts have a 3” inseam and are high-rise. I could easily swap the shorts for a pair of jeans. Or ditch the blazer and wear a puff-sleeve blouse. Lots of options! While this exact blazer and shorts are no longer available, we found some similar options in this same striking color.

If you’re not quite sure how to find the perfect fitting blazer, this post is a must read!

Vest & Cargo Pants Set

This next look is a little more casual. I mean…how chic is this matching set from Ramy Brook? This is definitely an unexpected, cool, and edgy look! Vests and cargo pants are very on-trend right now and this set covers both. The vest has a tailored, flattering fit with a V-neckline, an adjustable back, and pretty gold buttons. The matching cargo pants are the perfect lightweight fabric for summer. This head-to-toe monochromatic look is also super elongating and slimming. The pants are a little long on me so I’m wearing them with platform sandals. So, if you are 5’4″ or under you may need to have them hemmed. Just add a pair of slick aviator sunglasses to complete this fashion-forward look!

Keep scrolling for one more matching set outfit. Plus, key tips for nailing the look over 40 and over 50!

Gauzy Cotton Top and Pants Set

This next matching set would be so perfect for a beach or lake vacation, but it’s also a great everyday summer outfit too! I actually bought this super cute and summery set by Bobi at a retailer in my hometown. I was really hoping that I could find it available online so I could share it with you all because it’s just THAT good. And I did! The top is a really soft gauzy cotton. You can wear it on or off the shoulder, it’s cropped, has a lot of elastic, is very comfortable, breathable, and…versatile! I’m wearing it with the matching pants in the same comfortable gauzy fabric. This is the perfect day-to-night beach or lake outfit. Wear it over your bathing suit OR with some strappy sandals for dinner. It’s so breezy, comfortable, chic, and fun. You can also separate these pieces and wear the pants with a tank or tee and the top with some jeans or shorts. That way you’ll get even more mileage out of this very affordable set!

Tips To Wear Matching Sets

If you buy two pieces that are already a set…

• When I say “top” that can mean a sweater, blouse, jacket, blazer, etc. And when I say “bottom” that can be anything from shorts to skirts to pants… Your matching set possibilities are endless!
• Make sure you like the top and the bottoms. Remember that you can wear a top with jeans instead of their matching skirt or shorts. And vice versa. This creates more versatility. Don’t feel relegated to wearing only “the set”.
• More recently, a lot of sets come with a cropped top or sweater. This might seem scary, but when the bottoms or skirt is a super high-rise, like above the belly button high, then you may show a sliver of skin and that’s about it. It’s not as scandalous as you might think.

If you’re building your own set and searching for the perfect pieces…

• Remember that each piece in a matching set doesn’t have to match exactly.
• You can vary the tones and textures for a super chic look (like Melissa).
• If you do prefer the perfectly matched look but a specific top or bottom doesn’t come as a set, look at the same brand for a matching bottom or top. For example, my blazer above doesn’t come with the shorts. But I loved the color, so I looked at the brand to see if they had matching shorts, skirts, or pants…and they did!
• No matter what top or bottom you buy, make sure that you can wear both of them with different things, not just together.
• When in doubt, choose white or black for your DIY matching set. It’ll be much easier to get the look right.

Don’t forget to check out Melissa’s website here.  And, follow her on Instagram here. To get my blog posts delivered directly to your inbox, along with some amazing style resources, be sure to sign up for the newsletter here.
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