Wearing a Vest- Fall Menswear look with a Feminine Touch - Elegantly Dressed and Stylish
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Wearing a Vest- Fall Menswear look with a Feminine Touch


Hello friends!

Hope you had a great weekend. It was a busy one, as I voted early, went to the Opthamologist and got a new script for my glasses,  and enjoyed Verde, a Mexican restaurant that is only 10 minutes from us.  We still are loving the “taste of New Mexico” so I tried the least spiciest dish on the menu, and had a very good Agave Nectar Margarita!  Sunday we went and saw ” Dr Strange” with one of my favorite’s Benedict Cumberbatch! woo-wee! It was great!

Today I am wearing one of my favorite colors for fall ( perhaps I say this a lot) olive green. I decided to take this sweater dress( again, an easy dress to wear in the fall) and layer it with this menswear brown plaid vest. I have shared some looks with this vest or similar, over the year in the spring ( worn with jeans), last fall ( with a mini skirt and menswear booties) and now, with this look that has a bit of feminine and masculine in it.


The taupe Over The Knee boots were bought last season from Sole Society, as I loved the way I had seen them worn with white, also with various neutral looks. As you know, taupe is a neutral and can be worn with any color. I do love it with these colors- olive, browns.


Try some of these tips when adding an item of menswear to your look.

  1. Add a frilly scarf to the vest to give it a more feminine look when worn with jeans.
  2. Brogues in a more feminine color ( blush, tan) can be a fun way to add a feminine/masculine look when combining with a menswear vest.
  3. Try what I have shared today, wearing a structured vest over a dress.
  4. Wear a menswear vest with wide leg trousers, heels, and  a blouse with a pussybow for the more womanly touch
  5. Add a vintage brooch or as I did a tweed fabric brooch for a pretty look and additional texture.




I would love to hear your ideas on wearing a structured vest? Let me know your thoughts in the comments. I am also using some affiliate links to other vests, OTK boots, and sweater dresses. Enjoy! I am a big fan of OTK boots and have hinted to Santa about a pair 🙂

Outfit details: Olive Sweater dress; older, ( love in wine) ( LOFT) Vest: The Limited, OTK boots: Sole Society ( love these), Handbag: Rebecca Minkoff ( love this)


SHARE YOUR FALL STYLE AT TURNING HEADS TUESDAY LINKUP~ ! LOOKING FORWARD TO SEEING YOU THERE ! 🙂   Linking Up with  Visible Monday, Still Being Molly, Not Dressed as Lamb SHoe andTell , How I Spring Manic Monday, Monday MingleLinkup with Lisa

Jess xo

  • Pingback:Trending This Season- Vests- How to Style Them - Elegantly Dressed and Stylish - Fashion Over 50
    Posted at 01:00h, 13 December Reply

    […] I shared how I styled this vest with a dress in THIS POST. […]

  • Nicole
    Posted at 23:59h, 10 November Reply

    Thanks for linking up to Top of the World Style.

  • Julie @ Running in a Skirt
    Posted at 08:22h, 08 November Reply

    Such a great look! I love the details in it and these are another pair of fabulous boots!

    • Jess Jannenga
      Posted at 08:33h, 09 November Reply

      Thank you Julie, I love boots and these were easy to wear too ! xx

  • Megan_Ballard
    Posted at 01:01h, 08 November Reply

    I love the details on the tights and olive green is one of my favorites for fall too. xo ~ Megan The Fashionista Momma

    • Jess Jannenga
      Posted at 08:34h, 09 November Reply

      Thank you Megan, I am all for wearing textured tights in the fall! xx

  • Amy Christensen
    Posted at 17:33h, 07 November Reply

    Jess, I am so jealous that you saw Dr. Strange! I love Cumberbatch, but haven’t gotten out to see the movie yet. My hubby has a low threshold for superhero movies, so I may not get to see it until it is out on video…ha, ha. I like menswear inspired pieces and your suggestions for making the outfit feminine by pairing the menswear piece with a more lady like piece or accessories is a great way to blend the two and still look like a woman. Your dress is very cute and the vest is the perfect topper. Great accessories too. Love the look. – Amy

    • Jess Jannenga
      Posted at 08:31h, 09 November Reply

      Hi Amy, ys it was a great movie. Funny as hubby used to think I had a low threshold for superhero movies, I told hi,m I dont, just bad ones! Glad you enjoyed the post! xx

  • Highland Fashionista
    Posted at 15:41h, 07 November Reply

    LOVE your boots, they’re a great color for fall. All of the boots are coming out today, in every post I’m looking at, and I have been in the market for a new pair. I guess this is the universe telling me that I need to take some sort of action. Also love olive green, and it is so flattering with your red hair!

    • Jess Jannenga
      Posted at 08:32h, 09 November Reply

      Thank you! THese are so easy to wear. Low heel, suede. I love the OTK boots, but yes, it is your time. Lots of sales and good prices now too! xx

  • Anna Parkes
    Posted at 15:18h, 07 November Reply

    I love your OTK boots Jess, especially as you added those lace tights – very clever move! I’m a fan of mens vests too and have a few in different colours. I do the same as you – adding a frilly or brooch just gives a touch of the feminine as you say. Your handbag is a wonderful colour to wear with olive. Thanks for another lovely post.
    Anna x

    • Jess Jannenga
      Posted at 08:35h, 09 November Reply

      Thank you Anna for your comment. I am in love with OTK boots and always loved textured tights, a match made in heaven right? xx

  • robjodiefilogomo
    Posted at 08:18h, 07 November Reply

    I have a few of these vests in my closet—I’ll have to bring them out again!
    And I know my mom would absolutely adore that pin you’re wearing!!
    Fabulous look Jess!

    • Jess Jannenga
      Posted at 09:29h, 07 November Reply

      Thank you Jodie! I have a handful of vests, found this at a steal. Yes, you would look great in a vest.. you know me and pins! 🙂 xx

  • versatilestylebytracey
    Posted at 07:34h, 07 November Reply

    I love vests and the opposite juxtaposition of feminine/masculine touches in outfits. This is a wonderful example of that.

    • Jess Jannenga
      Posted at 09:28h, 07 November Reply

      Thank you Tracey, yes me too! Have a wonderful day! xx

  • Nancy
    Posted at 07:04h, 07 November Reply

    I absolutely love this look. I had a simular vest years ago that I wore on a wide brown skirt with edgy boots. I loved that look but couldn t wear the vest because it made me gap for air. To tight. It really looks so stunning on you!

    • Jess Jannenga
      Posted at 09:26h, 07 November Reply

      Thank you Nancy! I may wear this with brogues next time to change it up. I am a fan of vests and bet your outfit looked great. 🙂 xx

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