How I Add Drama To A Casual Look

Some women treat getting dressed as though they’re creating a work of art. Others simply put clothes on to cover their body. Most days I fall somewhere in the middle. Today I’m sharing my thoughts on creating various looks from the same core pieces and how I add drama to a casual outfit.

This time of year you’ll usually find me wearing jeans and a cashmere sweater of some kind. It’s a simple base that can be accessorized to create many different styles. over 50 fashion blogger jennifer connolly wearign chico;s outfit with gray fedora

If I wanted to look feminine, I could add low heels, pearls, and a curvy, soft jacket. For a sportier look, I could add sneakers, a baseball cap, and a zip-up jacket. You can get a classic vibe by adding nice loafers or driving mocs and a tailored blazer. For drama, I added a hat, ruana, and a touch of animal print.

I started with a patterned belt because a little animal print always jazzes things up. This belt (similar) has got to be at least 20 years old and is one of my favorites. I like the texture of the cow hair and the neutral color. I do have an orange-toned leopard print belt but went with this one to keep things cool-toned.
chico's wrap on jennifer of a well styled life

Once I’d decided on my pale gray boots (similar), my gray Fedora felt like a natural. Hat’s go a long way to help me feel pulled together, as well as protect my face from the sun. They do create hat hair, but they also cover a bad hair day, so there is that:)
fashion blogger jennifer connolly wearing chico's coolmax turtleneck, leopard belt and brixton fedora

You need to feel comfortable being noticed because wearing a hat makes you stand out. They add drama and a touch of mystery to whatever you wear them with.

I’m a big fan of Ruanas and capes. They’re dramatic and their “swish” makes them fun. Mine is a treasured gift from Chico’s several years ago, but this one is similar.  I kept the jewelry simple with tiny hoops and a large, artistic pin.over 50 fashion blogger jennifer of a well styled life wearing grey fedora and black ruana

I finished off my casual outfit with another dramatic (for me) touch, red lipstick. I seldom wear red because it can overwhelm my pale coloring but it’s a perfect shade when wearing black.


A simple sweater and jeans, or any casual combination can be dressed to achieve virtually any style recipe you want….based on the accessories you use.

What is your go-to base this time of year?

Thanks for reading and remember to wear what makes you feel confident.





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  1. Elaine @ Following Augustine
    January 16, 2021 / 10:08 am

    What a fun outfit! I agree with others here. I’d love to see how you change up the same basic jeans and sweater for completely different looks. Jeans and a sweater are my go to right now too.

  2. Rose
    January 15, 2021 / 11:11 am

    Love this outfit! I enjoy hats also, mostly just for golf. Since staying home so much I’ve been wearing tennis shoes more then my boots. Never would have done this in the past.

  3. KB
    January 15, 2021 / 9:26 am

    I am intrigued by this post!
    Please add another post where we can SEE you style “jeans-and-sweater” as described:
    “Drama: hat, ruana, and a touch of animal print (via a statement belt)
    Feminine: add low heels, pearls, and a curvy, soft jacket.
    Sporty: sneakers, a baseball cap, and a zip-up jacket.
    Classic: Nice loafers or driving mocs and a tailored blazer.”

  4. Lauren
    January 14, 2021 / 6:16 pm

    If you love hats as much as I do try Conner Hats (connerhats.com) They originate from Australia but are in Florida for their USA warehouse. They have more styles than you can imagine….they come in SIZES and if it is one of their one-size hats they can provide foam strips to adjust the size

  5. MRSBEN2
    January 14, 2021 / 4:41 pm

    As my grand daughter who is ten years old would say, ‘fashtastic’ Jennifer! As to starting with a few core pieces, to me it is similar to interior design. i.e.: Take a bed frame and mattress then by adding accessories you “can create many different styles”. ☺ -Brenda-

  6. Sandra Matthews
    January 14, 2021 / 4:14 pm

    I’m with you, my winter go to……jeans and cashmere or merino wool sweaters!

  7. Robin
    January 14, 2021 / 12:49 pm

    This may be my favorite look yet! Living in Palm Desert, we don’t have many days that require duplicate warm sweaters, however, I will start doing more layering–with leopard accents 🙂 — but with lighter weight pieces. When we do have those chilly days, I will follow your lead!! 🙂

  8. carol
    January 14, 2021 / 12:38 pm

    love your outfit but especially your hat! i have many but don’t wear them enough! my latest was TWO burgundy hats after seeing a commercial on tv!

  9. Judy Littler
    January 14, 2021 / 9:25 am

    I can’t believe how much the belt pulls your outfit together. Thanks for the tip! I’m definitely going to look for some new belts instead of wearing my old ones.

  10. Eve
    January 14, 2021 / 9:10 am

    Hats for me are not comfortable unless they serve a purpose like a sun hat, rain hat, knitted cap, or wearing a baseball cap to a sporting event. I wear a straw for gardening and fishing, so I do wear many. You just wouldn’t see that particular type of hat in my small coastal town. Oh, we do see cowboy hats at our rodeos. I’m afraid my small town may be in a fashionable rut.
    You do look smashing in a hat! Great look!

  11. Kat
    January 14, 2021 / 8:52 am

    Love this outfit on you!

  12. Kathy
    January 14, 2021 / 8:49 am

    Your outfit is very polished. My winter formula, too. Sometimes I add a cowl or shawl that I have knit. I also wear my own hand knit sweaters. I usually just add large earrings from my collection of vintage Mexican silver and I add booties if I am going out. We maintain a no shoe inside house, so Ugg slippers at home. Wish I could wear a hat like yours, but my hair is too short.

  13. jodie filogomo
    January 14, 2021 / 8:48 am

    Of course I love the outfit…it has sass and spunk. BTW, I adore the quote: “Some women treat getting dressed as though they’re creating a work of art. Others simply put clothes on to cover their body.”
    May I use that for an upcoming quote of the day on my blog and give you credit of course??

  14. Lurania
    January 14, 2021 / 8:44 am

    Once again you have focused on my outside world style zone! I love everything about this outfit!!! Like other comments I wish I had places to wear these! Being cooped up inside makes home comfort key… lounging in yoga pants or leggings with a comfy sweater is my new normal these days. I know the other ladies feel the same. Plus being retired…I have nowhere I MUST BE! A good book and a cup of tea is a perfect day.

    • Peggy
      January 14, 2021 / 2:47 pm

      I am very classic. I pull on my jeans, loafers and a blazer or cardigan. I do have some leopard flats and snake booties. They always perk up the look. I like minimal jewelry, either a necklace or gold hoops, pearl earrings or diamond posts. I have a few Coach purses (I have a purse weakness). Nothing brings the look up a notch than a nice bag and shoes

  15. Audrey
    January 14, 2021 / 7:40 am

    I like the sweater and jeans base as well. Now I will work on the different possibilities. Thanks for reminding us how a basic look can become great!

  16. Gail Ardiel
    January 14, 2021 / 7:27 am

    You have outdone yourself here. Love this look. I’m in Ontario and we are in Lock Down so I can’t can’t leave the house to show off the look. Will dress similar for lunch with my husband hoping
    For a better future.

  17. Gail Ardiel
    January 14, 2021 / 7:18 am

    You outdid yourself here. Love this look, my favorite. We here in Ontario are in total lock down so I can’t attempt to wear outside just in my house , which I will for lunch with my hubby.

  18. Joanne
    January 14, 2021 / 7:15 am

    Your beautiful red lipstick was the first thing I noted in the first picture! I love it! You look just fantastic.

  19. Jaci
    January 14, 2021 / 7:07 am

    Love this look Jennifer… adding the animal print belt makes it pop for sure.
    I love the look of the cool tone boots and hat, tying it all together. The cape looks super soft and cozy for this time of year. Is that a brooch or embroidery on this beautiful piece?

    Skinny jeans are very slimming for most body types and are still trending in the market place. (Hard to find a great pair of straight leg or boot cut jeans these days) I carry my weight in my booty and thighs. To balance the look I cuff my jean to show off the smallest part of my leg, my ankle! It also showcases that great bootie or flat.

    Thanks for the inspiration today!

  20. Debbie Monroe
    January 14, 2021 / 6:52 am

    Ii absolutely love this look! I have a rather large head (LOL) and have a hard time getting hats to fit but I would love to wear them. I will try the rest of this look this weekend though.

    I really look forward to all your ideas. I just wish this pandemic would be over already so I had more places to try them out.

  21. Susan
    January 14, 2021 / 6:24 am

    My favorite wa.y to dress is casual with a touch of drama,didn’t know how to describe it.It would be fun to more of this!

  22. Cindy
    January 14, 2021 / 6:12 am

    I love this look!
    Do you have any suggestions what style of hat to wear for a long, oval face?

  23. Paulette Levy
    January 14, 2021 / 5:14 am

    I too love your sense of style! Sometimes I think, “why didn’t I think to do that?” You are amazing and look gorgeous! So many great ideas……thanks!

  24. Paulette Levy
    January 14, 2021 / 5:13 am

    I too love your sense of style! Sometimes I think, “why didn’t I think to do that?” You are amazing and look gorgeous! So many great ideas……thanks!

  25. Paulette Levy
    January 14, 2021 / 5:13 am

    I too love your sense of style! Sometimes I think, “why didn’t I think to do that?” You are amazing and look gorgeous! So many great ideas……thanks!

  26. Diane B
    January 14, 2021 / 5:13 am

    Hats, yes! I love hats. Not so many places to wear them lately however but the day will come to start enjoying them again. I add my voice to those who like the suggestions for how to change a look and be able to soften the edges so to speak. Don’t know how you manage to come up with fun things all the time but really enjoy your posts.

  27. Bea
    January 14, 2021 / 5:13 am

    A lesson for me here is that when you stay with the same color for your layering pieces, it unifies the look while creating interest. Great look! Thanks, Jennifer.

  28. Pam
    January 14, 2021 / 5:11 am

    You look stunning!

  29. Jan
    January 14, 2021 / 4:49 am

    This blog was so useful! Starting with two basic pieces and building an ensemble from there. Maybe you could go a step further and display each of these options that you detailed.
    I find myself reaching for jeans and a basic, neutral top on most days. I love to layer with a cardigan or vest or flannel. Adding these pieces adds a comfort level that I have always been drawn to. I do need to focus on more shoe options. I don’t wear any type of heel anymore but still want a more finished look.
    Thank you for all the inspiration today! This was a fun read!

  30. Deanne
    January 14, 2021 / 4:27 am

    You look gorgeous in this ensemble Jennifer! You managed to wear a lot of black without having it drain your coloring! Stay safe

  31. Leslie
    January 14, 2021 / 4:24 am

    This outfit is “Everything”!!!! You look so gorgeous and amazing….. Love it👍👍👍👍👍

  32. Sandy A.
    January 14, 2021 / 4:18 am

    I liked your description of how to turn this outfit into classic, sporty, dramatic, or feminine. Could you please do a post where you do that and show us pictures?

    • Linda S.
      January 14, 2021 / 4:39 am

      I would love to see a post like this also.

    • Cindy
      January 14, 2021 / 4:40 am

      Yes! I was just thinking the same thing. The description was good but I’d love to see it in pictures or little video changing it up.

  33. Beverly
    January 14, 2021 / 4:14 am

    I love this outfit! It is so pulled together and would be so fun to wear. You look amazing in the hat.

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