How to Wear Fall Style Trends Over 50

It’s the second day of fall, and while our weather isn’t really cooperating, I am pressing forward, sharing fall clothes because many of you do live in climates that have cooled off. Here’s how to wear fall trends over 50.

blonde woman wearing houndstooth blazer and black turtleneck

Should you wear trends after 50? How much should you invest in them?

I believe a small touch of trend helps to keep us looking modern, so they’re worth knowing about. If you want to dabble in fall trends, add one piece or a nod to a trend. If this is the year that many trends appeal to you, go for it but keep your body silhouette in mind so you choose flattering shapes. If color is the trend, and they’re not your most flattering, wear it in an accessory, away from your face.

woman wearing blue jeans, suede boots, green jacket and floral shirt for warmer fall days


woman going down stairs wearing redelvet birdies plaid pncho and black v


woman wearing houndstooth blazer, wid eleg jeans, large chain necklace and wide leg jean trend

This fall, shrunken blazers, lug soles, loafers, chunky chains, and wide-leg pants are trending so I thought it might be fun to put them all together and see what we get. This is often a recipe for ‘tragic looking’ but I think this outfit passes the sniff test at a thousand yards because the pieces are exaggerated versions of classics. I do not recommend doing this unless your budget is unlimited:)

over 50 woman walking in wide legs jeans trend outfit

This time of year, plaid and houndstooth are always on-trend, so I started with borrowed from the boy’s, houndstooth schoolboy blazer.  It has a notched collar with a felt underlay that’s fun to pop up, for some attitude. The plaid has shades of chocolate, black, rust and blue, on a camel background with a blue and white striped lining.

Also see – How to Pop a Collar and Keep it Up

blonde woman wearing houndstooth blazer and black turtleneck

It’s available in regular and petite, sizes 0-24. Because it’s already short and I have a long torso, I opted for the regular length. It runs small so size up. They were sold out of my size so this one is way more shrunken than intended:)

over 50 fahsion blogger jennifer connolly of a well styled life wearing trendy wide jeans and loafers

Wide-leg pants and jeans continue to trend this fall. They’re not for every woman but they flatter women with wide shoulders and do help camouflage wide legs and athletic calves.  These jeans are very soft and stretchy with a nice high-rise and raw hem…which you could easily hem if you like. They’re sized from 0-14W and run true to size. 


woman sitting on bench wearing modern loafer trend

Loafers and lug soles are a popular trend this fall. Many are in patent leather which is often stiff so I was happy to find these loafers in matte leather. They’re also available in brown or a plum patent, sizes 6-12, in medium or wide width. I like the slight height elevation they give, without a heel.  They tend to enlarge the look of your feet, especially if they have contrasting soles and stitching.



woman wearing large chain trend

Larger chains are very popular this fall. I’ve spotted ones so large, they look comical, which is perhaps the point. This chain statement collar necklace is a good proportion for me because the scale is in line with my medium/large facial features and square jaw. You can wear this with or without the gemstone and also backward, as a lariat. 

over 50 fashion blogger wearing black turtleneck and wide leg jeans

A simple classic turtleneck rounds out this outfit which I folded over 3 times so it didn’t strangle my extra neck skin. 🙂

Are there trends you’re trying this fall?








  1. Loving your help!
    I’m “working on” the right look for 55 and working with high schoolers. LOL
    I have long silver mix hair, in the best shape I’ve been in a while with no time for self. In addition, full time caregiver for cancer surviving husband. Life is real

    1. High schoolers are a “tough crowd” :). Good for you. You do have your hands very full.

  2. Francesca B. says:

    Such a fantastic look Jennifer ! I so want that necklace for Christmas, l am going to show it to my daughter to “suggest” to my husband lol!!

    1. It’s the most amazing necklace! I think it’s my favorite of his of all time.

  3. Love the loafers. I agree that it gives a boost without heels and that is a great look for me. The wider legs on jeans look great on you. The blazer is a classic and not too pricey. On sale!
    Keep the geat looks coming. I wouldn’t have considered the shoes until now.

  4. I love the green jacket outfit. Just don’t like blazers or anything suits looking but I do like the blue on that popped collar. Lug boots are cute but just not for me. I don’t like heavy shoes but I love boots or booties. I have a new pair of burgundy this Fall but it’s just not cold here snd won’t be till Thsngiving or after.

    1. We won’t really cool off here until much later too, but I’m ready:)

  5. Mary Ann Pickett says:

    GREAT look with the plaid blazer and jeans….and the lug soles. Looks fabulous!

  6. I love loafers! I can see shoe shopping in the near future.
    Have to say a big NO to the shrunken blazer though. Too many years in the corporate world so a blazer feels too constrictive anyway and add shrunken, well NO, NO, NO. Looks cute on you but I would look like I was wearing something that didn’t fit anymore. I do like the wide leg jeans and I would like to see you style those another way. I am wondering how they would look with a more less constructed top. I miss getting dressed and going out!

    1. Lol, I hear you. This one is very shrunken because it’s several sizes too small for me:)

  7. Please tell about the sunglasses.

    1. The Sunglasses are from here , then I took them to my optometrist to have my RX lens put in.

  8. SUSAN BLAKEY says:

    Love those loafers and the plaid blazer! This is a good season for finding modern classic styles.

  9. Nicole from High Latitude Style says:

    Great looks. My favorite is the one with the blazer. This blazer is such a head turner and perfect with the black sweater and jeans. Such a posh casual fall outfit!

  10. Great post! I am on the hunt for a pair of loafers, and a plaid blazer. These are two trends I like. I think you look great in blazers. And the tip for keeping the collar popped…who knew! Loved the humor too. At our age, you have to have a sense of humor evaluating trends. We have been there and done that at least once!!

  11. Nice, versatile color combination on the blazer. None of these fall trends are good on my body shape, so I’ll just have to wait it out. thanks for showing us what’s out there.

    1. That’s the smartest way to approach trends. Happy Thursday

  12. Jennifer, you made me laugh before I finished my tea – you and your neck!!! (Which by the way doesn’t sag.) I liked the look a lot, though I think trousers in a color from the blazer would look super – even better than jeans. Loafers with lug soles: who knew?

    1. Happy Thursday, Maeve:)

  13. For my frame and height, wide legged pants must be longer than those shown and worn with at least a 2” heel. I don’t care for the ragged hem.
    The small jacket is nice but that style and fabric would need to be good quality. … lined, well fitting, good buttons. No lug soles for me. They look too clumsy and not comfortable. I do like that they give a bit of extra height.

  14. Mary Divine says:

    I usually pop the collar . Thanks for the tips on how to keep the pop !!!!! It makes you look a little taller ane I could use that at 5 2.
    I really like the dressing room shots, it shows how things look on real people.

  15. Love fall dressing…now if only winter didn’t come after fall. Anyway, I’m excited to wear ladylike combat boot (yes, i do think that exists), cowboy(ish) boots, loose leg jeans, and shackets.

    1. Ladylike combat boots do exist. I’ve seen them:)

      1. I often see the recommendation to buy a few trendy things per season to look modern. However, when the pieces are clothing items, one only looks modern on the days that one wears them. The only things that would have a modernizing effect throughout the season would be something like a bag or chain that is worn daily with everything. But most trendy items don’t fall in those categories. #confused

  16. Paulette Levy says:

    Classic and beautiful! Thanks for sharing.

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