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How to Try the Fall Fashion Trends

August 3, 2021

Welcome to our first official “transition to fall” blog post of 2021. I remember anticipating the arrival of the August edition of Seventeen magazine as a teenager because I knew it would be filled with fall fashions. Soon after devouring the magazine, I’d convince my mom to take me to the mall so we could hunt for all the chunky sweaters, menswear inspired trousers and fall eye shadow shades I’d seen on the pages. Undoubtedly I was back at the pool the next day, eating an ice cream and working on my sun tan. But the highlight of August was always thumbing through that fall edition of Seventeen, over and over and over.

Well, we’re not teenagers anymore. Not by a long shot. And most of us won’t be returning to school later this month or next either. But we can still enjoy the buildup to fall fashion. So that’s what we’ll be doing here at Dressed for My Day during the month of August. Of course you’ll still get to see how I styled my summer outfits in my Friday posts, but otherwise we’ll be talking all things fall. And today we’re squaring our shoulders and talking frankly about how to try the fall fashion trends…with more success and fewer regrets. Because fashion, dear friend, should be fun.

How to Try the Fall Fashion Trends

Personally, I consider my style aesthetic to be classic with a modern vibe. So, while I prefer rather classic outfit combinations such as jeans and sweaters or blazers, I do like to incorporate some modern trends into those looks to keep them fresh and contemporary. Plus, I find that experimenting with some of the trends is a great way to keep my overall appearance more youthful.

While I introduce a lot of trends here at Dressed for My Day, I don’t really encourage you to wear all of them. I’m just doing my job and sharing them with you so that you can be aware of them and perhaps learn a bit about styling them.

Throughout this month I’ll be sharing several trends that I think are the easiest and most natural for women over 50 to incorporate into their outfits. And I’ll try to make you aware of others, too. If you’d like to participate in some of the trends, here’s what I recommend so that you can have fun and fewer regrets.

My Tips for Trying Fall Fashion Trends

Kut from the Kloth Jeans and Vince Cardi
Kut from the Kloth Elizabeth Fab Ab High Waist Raw Hem Ankle Straight Leg Jeans (sold out) // Vince Slub Wool Blend Cardigan // P448 Thea Leopard Embossed Platform Sneaker // Halogen Teardrop Earrings (not in sale, but available)

Tip #1 – Remember this is supposed to be fun!

There may be some trends that really don’t resonate with us at all. That’s okay. Ignore those. But enjoy the opportunity to try something new with the trends that do strike you. And don’t let it frustrate you if something doesn’t work at first. Keep fashion fun!

Tip #2 – As you learn about the trends, make a mental or physical list of those that interest you somewhat, even if they seem a little extreme at first. I’m not suggesting you overthink this, but there’s a method to my madness!

Add a Blazer
 modern jeans (similar) // classic t-shirt // vegan leather shoulder bag // Elisa multi strand necklace // brushed gold teardrop earrings // Nordgreen Native watch // Easy Blazer from Everlane // black sports sandals

Tip #3 – Distinguish between trends and fads. A trend is a movement; it’s a direction in which things are moving. So trends last long enough for you to invest in and wear several seasons usually. Fads are a flash in the pan, here today and gone before you know it. So I prefer not to invest too much in fads generally, even though they can be fun to participate in, too, occasionally.

By the way, a fad is not bad. It simply doesn’t stick around as long. Don’t let anyone tell you that you shouldn’t participate in any fads. Remember tip #1!

I’d say, for instance, that wearing blazers with jeans is a trend. We’ve been seeing and doing that for several years now. But the more oversized or relaxed fit blazers may be more of a fad. In the same way, I’d classify straight leg jeans as a trend. But some of the gnarled or step or chewed hems are probably more of a fad.

Trends and Fads
NYDJ Straight Leg Jeans // sold out – similar jeans

Sometimes the difference between a trend and a fad is subtle. And sometimes what starts out feeling like a fad turns out to be a trend. But I do think it’s smart to think through the difference so you can strategize your participation.

One more distinction: Trends are usually new silhouettes or renditions of classic pieces. Think jean silhouettes, ways to wear animal print, iterations of classic pearls and blazer silhouettes. So if you invest in these classics worn in the trending way, you’ll get more bang for your buck. Whereas a fad is often something completely new…or new again.

corduroy blazer
See the original post (from two years ago) for more details.

The bottom line is to remember that a true trend is a direction, a movement. Sometimes if we don’t participate in any trends our wardrobe can begin to look outdated and old-fashioned. Know what I mean?

Tip #4 – Keep your personal style goals in mind. While fashion should indeed be fun, many of us want our clothing choices to accomplish something for us. We expect our way of dressing to set us apart in some way.

Perhaps you want your work outfits to make you look trustworthy, capable, approachable, intelligent or in control, depending on your job. Or maybe you want your day-to-day outfits to be very comfortable. And, if you travel a lot, you may need to create a wardrobe that is travel-friendly and very versatile.

Don’t sabotage those goals by adding trends that don’t work in the right direction.

Drape Collar Knit Blazer
See the original post (from last August) for more details.

Tip #5 – Establish or remember your own personal style essence. Have you defined your personal style aesthetic? I suggest you do that before you dip your toes in the water with any trends. Otherwise, your style will soon be all over the place.

If you need help identifying your own personal style, you might want to read this post or take this quiz.

Tip #6 – Think about how the trend will work with your body shape and proportions. Now don’t start ruling things out just yet. But do at least consider how a trend will work on your body…from the best you can tell without actually trying it.

Consider things like:

  • what it will accentuate or draw attention to
  • how much space it will take up on your frame
  • how it will play in proportion to your size
  • where it will hit on your body
  • where the lines will cross your body
  • how it may divide your proportions
  • how it may define your shape
Eileen Fisher Lantern Pants button cardigan
Treasure & Bond Puff Shoulder Cardigan (sold out) // Eileen Fisher Crop Wool Lantern Pants (size down) // Halogen Teardrop Earrings (not in sale, but available) // Aquatalia Dayana Water Resistant Stretch Bootie (runs small)

Tip #7 – But don’t rule something out that really intrigues you without trying it…several times. Even if you think it may not work on your frame, if you like something, you should try it.

When new silhouettes especially are introduced, it’s hard to know exactly what they will look like on us until we try them. Just because someone somewhere told you that petite women can’t wear kimonos, don’t let that keep you from trying one. Or just because you think a pair of cropped pants might make your legs look short, don’t hesitate to try them on.

Often these preconceptions can be changed simply with the right styling tips. Or maybe you just need to look for that trend in a different length or cut.

What I Wore Friday (3)
two button blazer // blue twist neck tee // similar jeans from Talbots (my Kut from the Kloth are sold out) // black ReNew sport sandals // earrings // necklace in black drusy // watch (use code KAYHRMS for 15% off your order)

Tip #8 – Watch to see how your favorite brands interpret the trends. If you already shop a few brands that you enjoy and that generally fit you well, lean into those brands when you decide to try some of the trends. For instance, I know many of my readers love to wear clothing from Talbots. So check out their iterations of trends such as leopard print, modern pearls, joggers, blazers and, yes, even relaxed fit jeans.

Everyday Relaxed Jeans at Talbots

Tip #9 – Choose one, two or three trends to try this fall. You can choose more if you’d like, but beware of incorporating too many trends into a single outfit. The point is “don’t bite off more than you can chew,” at least at a time.

Tip #10 – Consider how you can incorporate your chosen trends into your wardrobe and personal style essence. Once you’ve selected a trending garment or accessory to bring into your wardrobe, play around with how you can wear it so that your outfits still reflect your personal style. In other words, keep your outfits truly representative of you while including something new. That means you’ll probably want to just incorporate one trend at a time in some cases.

Tip #11 – Investigate how you’ll need to style the new trends. For instance, you may need to wear certain types of footwear with those new jeans. Or you may need some no-show socks with those fashion sneakers. And you may want a specific kind of bra with that top that has the cutouts.

See the original post for details.

Tip #12 – Try on several different variations of the new trend, if needed. You may not have this luxury if you’re shopping from home. But keep in mind that some stores, such as Nordstrom, do make this easier because they provide free shipping and free and easy returns.

The more you try something on, the more your eye will adjust to seeing it on you. And the more likely you are to find the right fit, proportions, color combination for your wardrobe and style.

Tip #13 – Invest in closet classics and wardrobe workhorses; spend less on trends you’re not sure about and even less on fads.

Tip #14 – Consider trying trends first in accessories, shoes or inexpensive tops, if applicable. For instance, it’s probably wiser to first try animal print in some inexpensive leopard print shoes or scarf rather than a coat. (Leopard print coats are trending this year, by the way.)

Tip #15 – Try on and style your chosen trends in multiple ways in the comfort of your home. Take photos on your phone so you can check out the looks with more objectivity. You might even send the photos to a forward thinking daughter or daughter-in-law or friend to help you assess the look. (Beware of sending these photos to the wrong people. Select people who are open, fashion forward and kind!)

Oversized Silhouette
See the original post for details.

Tip #16 – Be courageous and wear your trend with confidence and joy. Remember, this is meant to be fun. And you’ll never pull off a new trend without at least a modicum of confidence. Smile. Carry yourself with good posture. If someone says something unkind or questionable, toss it off and carry on!

You might want to check out my recent post, The One Characteristic Every Stylish Woman Has in Common.

Tip #17 – And then if you feel like you didn’t quite get it right the first time, try again. That was one day, one outing. Learn from it. None of us get it right every time. I certainly think I styled these Eileen Fisher lantern pants (sold out, but these are similar, not in wool) better below than I did above. And thousands of women saw me in the photo above. Ha! But that didn’t keep me from trying again.

Eileen Fisher Lantern Pants and Grey Cardigan
Club Monaco Shrunken Cashmere Cardigan // Eileen Fisher Crop Wool Lantern Pants (sold out, similar) // Halogen Teardrop Earrings (not in sale, but available) // Paul Green Dazzle Loafers (available, but not in Sale)

What trends are you thinking about trying this fall? We’ll be looking at more trends in the coming weeks. But I’ll also be sharing an updated fall wardrobe essentials list and classic styles as well.

I hope you have a great day. Now, go do something very summery!

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Blessed for My Day

Did you know that Esther is the one book in the Bible in which God is never directly mentioned? But He’s there! In fact, that’s part of the significance of this historical book. Even though God is never mentioned by name in this account of the Jewish people living under a foreign king’s rule, God is at work on their behalf.

When you turn on the news tonight or read the paper and you see or hear no mention of God, do no fret. He is here. He is at work.

During that night the king could not sleep so he gave an order to bring the book of records, the chronicles, and they were read before the king. It was found written what Mordecai had reported concerning Bigthana and Teresh, two of the king’s eunuchs who were doorkeepers, that they had sought to lay hands on King Ahasuerus.  ~ Esther 6:1-2

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xoxo, Kay
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26 thoughts on “How to Try the Fall Fashion Trends

  1. I would like to see a post on styling the lug sole boots for the mature woman. I love Paul Green and bought the Jackson style boot on the Nordstrom sale. Having second thoughts but so fun! I have a very casual wardrobe.

    1. I will definitely be sharing how to style that trend. I have some (not the Paul Green, not others) myself. And others have already asked too. Hang onto them! We’ll get there!

  2. Hi Kay. I can remember the excitement about running to the drugstore to get the August issue of Seventeen magazine filled with all the fall fashions as a teenager, too. The magazine was so thick back then and it was fun to spend hours looking at the fashions and advertisements. I never could really afford those new clothes back then but still it is a great memory.

  3. Thanks again for defining what trends and fads are. It can be a little confusing when you go shopping or look online and look at the new silhouettes. I do try to do a couple trends a year. Sometimes they work for me sometimes not. I personally miss sometimes people dressing up more. Like for church. I know God doesn’t care what we wear But I do like to look nice when I go to God’s house
    Yes we must always remember even during these trying times that God is always there working in the background taking care of us. Bless you

    1. Generally the most universally flattering length is right at your leg break or slightly above. But it really depends on your body shape and proportions. I suggest trying on several styles and seeing what looks best on you. Be sure you’re wearing the style of jeans or pants and shoes you might wear with a blazer.

  4. I begged my Mom to givrpe me jobs so I could buy Seventeen because she wouldn’t. I spent days drooling over those beautiful models – remember Twiggy? I like your ideas about fads and trends so if I think something I like is a fad,I shop less expensive brands ( like old navy or Target) and sometimes I end up loving those fads and wearing them for years. If I am going to invest a lot of $ I took a hint from you and take my trusted I pad shopping and have a sales person take my pic – they love doin that. That wayI can think about it for awhile – sometimes just seeing it that way the first time decides it for me, other times I look at it several times before I decide.
    I look forward to your post everyday. God Bless!

  5. YESSSSSS! I am so excited about this, the first of fall 2021 posts! I literally stopped exercising and started my hot tea, so I could “snuggle in” with this episode! Magazines are definitely NOT what they used to be, but that brought back some lovely memories. Blessings to you, Kay, as you continue to bless us!

  6. One of the things I so appreciate about following your blog is your inspiration to try some trends. So I have added some animal print accessories and even a sweater these last few years. That’s pretty trendy for me! I’m not an “early adopter.” Only had one scarf before. Now, as I acquire more pieces, I’d love it if you’d do a post on how to mix them together. Do you ever style two animal prints with the same outfit? Leopard scarf w different leopard shoes? If so or if not, what are you looking for to pull the outfit together? Do you ever mix them with other prints? I like my leopard print necklace with my indigo small striped tee. But wondering about other possibilities. Snake sneakers with a small floral print scarf? Maybe you’ve already done a post like this? Thanks for any help.

  7. Oh yes, I have great memories of the Seventeen magazine! I bought a pair of the Dolce Vita chunky booties from the NAS and am looking forward to trying to style them once my fall/winter clothes are out of the attic. As an almost 65 year old, I have finally recognized that I don’t need to jump on the bandwagon for all of the trends. Not only do I consider my style essence, but I also take the area in which we live into consideration. I am still on the hunt for a pair of lantern pants that are in my price range, and will need guidance on how to wear them during the cooler months.

  8. I feel about fads the way I do about music. I have the genre I listen to most of the time but I do listen and appreciate other music but I don’t invest much into it. I do it for fun.
    I think the lantern pants are great and I bought a pair but I’ll still buy straight leg for my basics.
    God knew ahead of time what would happen to this old world. Evil may trend for awhile but I’ve read the back of the book. Good wins. Fear no evil for aged is with you.

  9. So ready for Fall fashion Kay….great descriptions of trends and fads. I am beyond grateful God is always here. Speaking of Esther, my husband and I saw the live production of “Queen Esther” in Lancaster, PA while on vacation this summer. It was phenomenal….like the Bible was brought to life with outstanding and talented actors and actresses. I am looking forward to your upcoming Fall posts.

  10. Fads: I desperately needed a dress for a wedding once, but stores only carried cold shoulder sleeves. I refuse to buy something that will be outdated in 3 years. I go for long term purchases. PS. I LOVD Seventeen!

  11. Hello
    Funny that you mentioned Esther! I live in Maryland and we are about 1.5 hours from Lancaster P.A. This is the home of sight and sound theater. We just saw Esther there a few weeks ago. Really well done. Have you ever been?

  12. Seventeen magazine was the best thing ever and back to school shopping was so much fun. I remember saving up my babysitting money and buying a new back to school outfit. Here in Virginia our falls come late. It often stays warm through the end of October, so I curb my enthusiasm for rushing out to buy fall clothes. I have enjoyed the new shape of pants, and incorporated some in fall colors that I can wear with lighter weight tops for back to school-I’m a teacher. With some of the new trends it’s all on styling. I watched a YouTube video where a women suggested wearing wide leg pants a little lower on your hips for a nicer silhouette. So, I tried it. It did make a difference, just a little “cooler” looking.

  13. All the August fashion magazines were thick with fashion back in the day. I remember pouring over Glamour magazine as well as Seventeen. I just ordered the leopard print sweatshirt from Talbots as my “trend to try” this fall. I can think of several ways to style it. I am also eyeing the casual blazer look too. Thanks for the reminder of a fun memory!

  14. Hi Kay – Love following your posts and your style. I know you used to wear your hair curly and now have it straight. I can do the same thing with my hair but have issues with frizz (and I live in the PNW where humidity is low this time of year). Can you share any products and or tips for dealing with frizz? Another question, I purchased a faux moto jacket at the NSale this year. It is asymmetrical and I am a pear shape. Does the jacket need to look like it has to zip? If I size up to go around my middle area, then it looks too large on shoulders and sleeve length plus excess fabric across the chest…

  15. I have been following you for at least two years, since I first discovered you. You have a lovely classic style, overall. And I admire your posts on spiritual and character building. I just have one complaint. The shorter length pants visually cut off the leg length and I cringe when I see them on any fashion blogger and scroll through faster. Especially the newer baggie leg styles. A fad that needs to go, they’re not attractive on anyone. (I know, it’s my opinion, but as a design student of balance and proportion, it’s very off putting.)

    1. Hi Diana. I’m glad you enjoy the blog for the most part. Thanks for letting me know. You might want to keep in mind that I’m 5’8″ and my legs are pretty long. The photos may not convey it, but I’m not terribly concerned about visually cutting off leg length. And the truth is that shorter lengths are in style. I try to share them styled so that they optimize leg length. For instance, this is why it’s important to wear the right shirt length and shoes that continue the line of the leg. It so happens that I just this morning purchased a couple of pairs of full length boot cut jeans that I’ll (hopefully) be sharing in the next few weeks. But I will continue to show shorter or cropped and ankle length jeans, too. I’m not a slave to fashion trends, but I do enjoy keeping up with what is current and participating in the trends I enjoy.