The 5 Most Controversial Fashion Items Over 40

I get the question, “Can I still wear (insert controversial fashion item) if I’m over 40?” I’ve been asked about everything from skinny jeans to denim shorts to espadrille wedges and SO much more! I like to say that you can wear anything you still feel comfortable and confident in. But…as women over 40, we need to be careful about how we wear these controversial items! I’m sharing five of the most controversial and most asked about fashion items and how you can wear them over 40.

Age Appropriate Denim Shorts, Fashion blogger over 40 Busbee Style wearing AGOLDE denim shorts, a black tee, and panama hat at Lake Powell

#1 | Denim Shorts

Denim shorts…one of the most polarizing items! Half of you say it’s time to throw them out while the other half love them! I’m a big fan of jean shorts during the spring and summer. I’ve done an entire video on how to wear shorts over 40 that’s a must-watch! My favorite denim shorts are these super high rise shorts by Agolde.

Quick Tips for Wearing Denim Shorts Over 40

  • If you’re wearing shorts, add coverage on top with a long sleeve blouse or third layer like a blazer or jacket.
  • Find shorts with a longer inseam. I suggest at least a 3” inseam or longer!
  • I also love shorts with roomier legs because it actually makes your legs look slimmer. A higher rise will cinch that waist too!
  • Dress up your shorts! Denim shorts are casual but if you pair them with dressier pieces, they look more elegant.

Amanda Uprichard Tops, Fashion blogger Busbee Style wearing a beige puff sleeve top by Amanda Uprichard with dark wash skinny jeans, Valentino sandals, Julie Vos bracelet and ring, and Kendra Scott adjustable necklace in Texas

#2 | Deep V Necklines

The next controversial fashion item…v-necklines! There’s a fine line between wearing a classy, sexy deep v and showing too much cleavage. Some of us just aren’t comfortable with that part of our body, some don’t love the skin on their décolletage, and others think it’s just inappropriate. I completely understand not wanting to show off that part of your body. But I wouldn’t say that women over 40 can’t wear v-necklines.

Quick Tips for Styling Low Necklines

  • If you’re going for the sexy deep v look but aren’t sure if it’s appropriate, add a pretty lace cami or bralette underneath. You’ll still get the sexy look but take away the anxiety of the neckline possibly being inappropriate.
  • For normal v-neck tops, I look for the v to end right above my cleavage to avoid too much showing.
  • This changes for a special occasion or statement pieces. If you’re going for a statement piece, you can get away with a deeper v sometimes!
  • If you’re wearing a deep v, add coverage with jeans or a longer hem.

fashion blogger over 40 showing how to style a crop top over age 40 in age appropriate outfit

#3 | Crop Tops

I’m not a huge fan of crop tops but I do own a few! When women ask if they can wear them, I do have a few tips!

Quick Tips for Rocking a Crop Top After 40

  • Pair the crop top with a higher rise bottom so you don’t show any belly.
  • If it’s cropped, make sure it’s not tight. A looser fitting crop top is easier to style and won’t be too “young-looking.”

How to wear leggings over 40, featuring black Spanx leggings, Sam Edelman over the knee boots, Barefoot Dreams cardigan, and two-in-one layered sweater worn by fashion blogger Erin Busbee of in Telluride Colorado

#4 | Over The Knee Boots

Every fall/winter season you all ask me if over the knee boots are out of style. OTK boots are still in style and can look super chic and sexy if you style them correctly. I shared three ways to wear OTK boots here.

Quick Tips for Wearing OTK Boots

  • Avoid pairing OTK boots with short skirts and dresses. Many influencers on Instagram do this and it’s fine if you’re in your 20s…but styling them with jeans or pants is much classier for women over 40!
  • Going with a basic black, brown, or taupe colored boot will also look more classic and be easier to style.
  • There are a lot of OTK boot styles out there. I’d look for some that are high quality with no visible hardware or stitching, a pointed toe, and a block heel. I’ve tried a few brands and my absolute favorites are the Stuart Weitzman pair. They’re an investment but you can find some that are more affordable too!

Blonde woman wearing jeans, layered sweater, Barefoot dreams cardigan, Saint Laurent boots, and a Rag & Bone hat in Telluride Colorado sharing chic and casual looks for busy moms

#5 | Leggings

Leggings are probably one of the most controversial fashion items no matter what your age! Some people feel very strongly you can’t wear leggings as pants! I’ve styled leggings a couple of different ways and believe you can definitely wear them! They’re comfortable, easy, and can be dressed up or down! I’ve shared how to wear leggings and look chic in this video and post.

Quick Tips for Age-Appropriate Outfits With Leggings

  • Cover your bottom with longer tops and sweaters or a third layer.
  • Shoe choice is important…your shoes can really elevate a leggings outfit!

What are some controversial fashion items over 40 that you have questions about? Please share in the comments!

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Join the Conversation

6 thoughts on “The 5 Most Controversial Fashion Items Over 40

  1. This is a great posting. You are spot On with your comments — especially anout leggings. Leggings are not Pants, lAdies! Cover those butts! I’m over forty and i wear leggings frequently, but only with DRESSES, tunics, or a third layer.

  2. My mother tells me i can no longer wear a mini skirt! Also short dresses. I wear them anyway but wou love advise, so i dont loo rid!

  3. Erin,
    I love your channel and an happy to now get your newsletter. I started watching you in Fall of 2019 and started building my wardrobe then. I always bought things I liked or were pretty or flashy or unique or on sale but felt like i never had anything to wear. I’ve learned so much from you and a few other youtubers that now at age 50 I finally have found my own individual style and am building up my basics. Looking forward to your bag too!
    Thank you!

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