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10 Ways To Look Stylish This Fall Over 40

October 14, 2021 By: Nada Manley2 Comments

It’s the little things, really, that can elevate the everyday outfit and make it feel special and stylish. And that’s what today’s post/video is all about.

Like every season, fall brings with it a unique set of challenges and opportunities when it comes to style. We want to look festive without feeling silly, warm without looking like a woolly mammoth, and stylish without looking like a fashion victim. It’s a tall order.

Fortunately, a stylish fall has less to do with major overhauls and more to do with small tweaks and easy updates to the outfits you’re already wearing. Here, 10 simple ways to look stylish this fall.

Don’t Be a Slouch

A slouchy sweater sounds cozy and cool in theory, but in real life, it is often too warm, too baggy, and too bulky to be truly stylish. Slouchy, oversized and boxy sweaters are only flattering if you’re very tall, slim, and small-busted. Otherwise, swap your slouchy style for something with a bit more flattery built in, whether it’s a lovely v-neck or a slightly fitted button-front cardigan.

  • A sweater with some structure and shape is a more flattering choice.
  • This v-neck sweater from Banana Republic is a stylish option.
  • A slouchy sweater worn with a flowy skirt is a shortcut to frumpiness unless you are tall and slim
  • This slouchy sweater is easier to wear because of the exposed shoulder

Add a Hat

Does your outfit feel boring and a little incomplete? A hat is an easy way to instantly add style and create a fun and finished look that is perfect for fall. I love wearing dresses year round for comfort and style, but sometimes they can look a little boring. A hat adds instant just the finishing touch a dress outfit needs, and a great hat has the ability to turn basics into outfits.

  • A hat elevates this simple outfit
  • The trim on this hat adds pattern and texture to the simple outfit
  • Fall basics get an upgrade from a hat

Update Your Boots

I’m about to have the same friend-to-friend chat about boots that I had about skinny jeans. It’s time for a change. And while skinny jeans can still be worn stylishly, the round toe brown booties of 2015 need to be retired. You know the look, because it was everywhere for what felt like a decade, and now it’s time to move on.

The new boots are so tempting and so pretty, and they’re an easy way to update all of your existing clothes. The key trends to look for include knee-high pointy boots, usually with a kitten or stiletto heel, booties with pointed or square toes and a cool sculptural or block heel, slouchy suede 70s style boots and chunky, thick-soled lug or combat style boots. I’ve added a few of my faves to my catalog right here.

  • A sculptural heel is a chic update
  • These pointy-toe knee high boots from Vince Camuto feature trendy embossed leather
  • A slouchy pair of boots has a chic 70s flair
  • These slouchy boots from Anthropologie are chic and comfortable
  • An affordable pair of boots from Lulu’s
  • These high-end Marni combat boots are a big trend this season, but modified versions are more wearable for most of us
  • A blocky and bulky pair of slouchy boots, like this style, is not a flattering choice for fall
  • The ubiquitous 2015 look, with brown round toe boots and an infinity scarf
  • A pair of boots from Neil Rodgers on Sincerely Jules

Try a Long Outer Layer

Playing with proportions can be an easy way to add interest to an outfit, particularly one involving wardrobe basics. One of the most flattering ways to do this, of course, is to add that all-important completer piece in a longer length. When you throw a blazer, casual jacket or cardigan on over separates, you have a look that is polished and stylish, and of course, you have an additional layer of warmth.

  • A long cardigan adds interest to simple pieces
  • A white tee and black jeans get dressed up with a blazer
  • A contrasting cardigan over a dark neutral column of color is a chic choice

Consider a Wrap

The perfect answer to a breezy day in early-mid fall, a wrap also happens to be a trendy choice this season. Ponchos, capes, and their easier-to-find-and-wear cousins, the wrap, were all seen all over runways for the season. The key, however, is to wear them without them wearing you. Choose a style that isn’t too overwhelming, boxy, or long, and make sure it hits at a flattering spot on your body.

Pair Dresses With Boots

I know the idea of wearing boots with dresses is nothing new. I have been wearing my booties with dresses for years. However, with the change in both dress lengths and boot styles, this look has had a welcome makeover. The new looks have some of the polish and glam of the late 70s and early 80s, but with more flattery. Try a pair of slouchy boots with a midi-dress, especially if you don’t love your legs. Another strategy is to pair boots with a dress that is potentially stuffy. It immediately creates a more relaxed look.

  • Light boots and a short floral dress is a great fall option for women in warmer cliamtes
  • The look of high boots and a classic dress never goes out of style
  • Chunky boots update this simpl
  • I have worn booties with dresses for years, but this season I’m mixing it up a bit

Try White, Not Black

Black and other dark neutrals are classic choices for fall, but that’s also what makes them obvious. White, cream and other light neutrals are a more unexpected choice and a more high maintenance one, which is why they can also be so chic. Try layering light neutrals in varying shades and textures together (don’t worry so much about matching) for a fresh and stylish fall look.

  • A simple but stylish statement in white
  • Textures and varying colors add interest to this look
  • Layers of cream create a cohesive style
  • Nubby and silky textures keep this look interesting

Try a Trench

I know I’ve already mentioned the chic-ness of a long over short look, with a long outer layer, but a trench deserves a category of its own. A simple trench is one of the few truly timeless pieces in your wardrobe, and is an easy way to instantly add polish to the simplest outfits. Tee and jeans? Add a trench. Simple dress? Add a trench. It goes over almost everything and makes you look like a movie star. Choose a style with a belt for maximum flattery.

  • Casual pieces get an upgrade with a trench
  • Camel and white is a classic chic combination
  • Elevate your basics with a trench

Try a Twilly

A twilly is a long thin scarf, usually of silk, with a pretty name, so I chose to use it for this category. It’s also the simplest scarf style to wear in a flattering way, because it’s not too big and bulky for petites and doesn’t add weight to a fuller bustline. Tied around the neck for a flash of color and pattern, it’s an instant outfit maker (and neck skin disguiser). It also looks fab worn on the wrist, the waist, and the arm of a purse.

  • Add color and pattern to a solid outfit with a twilly
  • Neutrals plus neutrals is a timeless combination
  • A feminine substitute for a necklace

Which of these fall styling tricks will you try in your wardrobe? Let me know in the comments!

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Comments

  1. Nada Manley says

    October 17, 2021 at 6:00 pm

    I understand your frustration, but your toes don’t actually go into the point in a well-made boot or shoe. So you actually do have some toe wiggle room. But all of these ideas are just suggestions, of course, and you have to choose what works for you!

  2. Heidi says

    October 15, 2021 at 9:10 pm

    I am soooo unhappy about the pointy boot trend! Wide toe boxes are necessary for natural foot motion and healthy feet and body. Why should we let these fashion designers decide what’s good for us?

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