Romantic Dressing Over 40 ~ A Style Interview With Elegantly Dressed and Stylish

Is romance dead? Not in Jessica Jannenga’s closet!  Jessica is the creative force behind Elegantly Dressed and Stylish, a 40+ blog that celebrates romantic, feminine dressing.

The 47- year- old fashionista from Charlotte, North Carolina, has a passion for all things pretty and a soft spot for vintage classics.  Florals, lace, and Jessica’s fiery red hair are all part of her well-known signature look.

I recently had the chance to chat with Jessica about her vintage-inspired style and romantic approach to dressing at midlife and beyond. Here’s my interview with this Fabulous After 40 Styleblazer.  

Deb: Your style is very feminine and romantic, but you say you are a tomboy. That’s a contrast! How did you arrive at your signature look?

Jessica: Growing up, I was a tomboy. I played many sports, including football in front of our house, hockey in the driveway, lifting weights, played kickball, softball, etc. I was on a sports team in school for basketball. I have always loved camping and hiking, and I met my husband taking a rock climbing class.

I wouldn’t exactly say I am a tomboy at this stage, but I still love sports and do what I can, such as swim and walk.  I always liked the romantic look of lace and florals in fashion shows etc. My love of wearing touches of vintage springs from my interest in different eras. The pieces I buy have a story behind them too, which fascinates me too.

Deb: Let’s talk about romantic dressing- What does it mean to you?

Jessica: To me, romantic dressing is about wearing fabrics like lace, faux fur, cashmere, chiffon, silk, and details such as ruffles, florals, jewel embellishment, and quilted handbags. These things evoke a certain feeling or mood when I dress romantically. I also love shoes with bows.

Deb: Whose romantic, feminine style inspires you?

Jessica: As far as a designer, I love Ted Baker. He designs bold pastel floral dresses and has some dainty purses with fabulous floral prints. Grace Kelly dressed both romantically and classically.

Deb: Florals and lace are part of your look.  What’s your favorite way to style them?

Jessica: I love to style them by adding texture,  like a lace skirt with a tweed jacket or sometimes a soft cardigan and faux or vintage fur and brooch. I have some floral 60′ s pencil dresses for spring that I can’t wait to wear. I look forward to styling them with some vintage or vintage-inspired block low heel or t-strap shoes. I also love velvet and would add a jacket or vest for a rich textured look.

Deb: You let it be known that you don’t subscribe to “over 40 fashion rules.” Give us some examples of rules you find silly.

Jessica: Well, not wearing mini skirts, leggings, or over-the-knee boots would be some examples. I wear mini skirts with tights in the fall/winter and love to balance the proportions with an over-the-knee boot. I also think confidence is an important part when you are choosing what to wear. Over-the-knee boots are also wonderful for elongating the leg. I suppose I feel strongly about all this because who makes these rules?

Deb: If you could choose only one outfit from your closet, past or present, to wear for the rest of your life, which would it be and why?

Jessica: I probably would choose this red and white floral 60s pencil dress. It is made of very comfortable neoprene fabric. It has a flattering fit; red is one of my favorite colors, representing my style quite well.

Deb: You have a health challenge that requires you to make some fashion accommodations. Tell us about that and how you work around things?  

Jessica: I have Ehlers-Danlos Type III, an incurable chronic pain disease. I  have a genetic defect in my connective tissue, the tissue that provides support to many body parts such as the skin, muscles, and ligaments. My joints are unstable and can dislocate. Because I am missing a protein, my body is challenged to “hold itself up” due to hypermobility, thus creating muscular knots under the skin. This causes pain. (Sorry for the long explanation!)

Eight years ago,  when I was first diagnosed, I wore all black, soft cotton clothes, and sneakers and was only able to go to the end of the street and back with my pups and spent most of my time on the couch.

Presently, I do much better, but I have heightened nerves, so I have only recently begun to wear jeans, as the material would bother me. Because I can not stand for long periods, I do not wear stilettos or high heels but have managed to wear 1-1.5 square inch heels, and I add orthotics for extra support and padding. I also do 95% of my shopping at online thrift stores like Poshmark.  I shop at stores in which the sizing is consistent and have free return policies. I can not stand for long periods, so I am not a fan of mall shopping.

Deb:  Tell us more about your love for Vintage. How do you suggest women over 40 do vintage without looking old?

Jessica: I need to do a post on this!! I wear faux fur, so I love fur stoles, capelets, etc., to get that vintage-inspired look. However, I do have one piece that is a true vintage capelet from 1926, which still had the label and initials inside. It makes me feel as if I am walking in someone else’s shoes in a different era.

I do most of my vintage shopping on Etsy, and I collect vintage brooches. I love hearing the stories behind the pieces. Start by wearing one-pieces, such as a brooch or vintage handbag, and see how you like the look. Dressing head to toe in vintage can be overwhelming or look too costume-like. I love to add a faux stole and a vintage brooch or shoes that I found. Just add pieces here and there. One doesn’t have to look like one stepped out of a time machine!

Dressing head to toe in vintage can be overwhelming or look too costume-like. I love to add a faux stole and a vintage brooch or shoes that I found. Just add pieces here and there. One doesn’t have to look like one stepped out of a time machine!

Deb:  You wear a lot of dresses. What are your favorite dresses and why?

Jessica: I always feel more dressed up and pretty in a dress. I will reiterate that comfort is also key for me, and dresses are wonderful as they are quite comfortable and make getting dressed relatively easy. I love taking a dress I wore in the summer and transitioning it to winter by adding a pair of boots, a new blazer, and some vintage jewelry in the fall. There is a lot one can do with dresses. My favorite dresses are the Megan dress from Karina, a style out of the 40s with short sleeves and a flowy bottom half. My favorite would be the pencil dress, as I love the fitted shape and either Peter Pan style collar or sweetheart neckline. I find some of these on eBay or ASOS.

Deb: You wore a gorgeous dress when you attended NYFW. Tell us about that special night and how the dress made you feel. 

Jessica: Thank you! The dress was picked instantly when I found it on Bloomingdale’s site during a big sale!   The designer was Tadashi Shoji. I saw it and said, ” That’s me!” I loved the lace, the defined waist with satin trim, long gown. It made me feel quite glamorous as most people were in black, and I think it was myself and one other woman in red. Red has always been one of my favorite colors, and I don’t believe redheads can’t wear red ( another silly fashion rule!)

Deb: I see a lot of burgundy and olive green in your outfit posts. Are you picky about the colors you wear? 

Jessica: In the fall, burgundy, plums, and purples are my favorite colors, and I love olive and other shades of green. I used to wear all black in college, but now I feel it makes me look a bit stark, with fair skin and red hair. Black can work if I have

Black can work if I have some color near my face, a scarf, blouse, etc. I love to wear color as I feel it shows my mood and helps my mood when I wear color. It feels nice on me.

I am picky and feel that jewel tones are great colors for redheads; I love blush and other pastels. Yellow can be tricky to wear, but a soft butter yellow will work. I am looking to add more blue hues to my wardrobe. I also love fall colors such as rust, reds, and greens.

Deb: You say fashion should show off one’s personality. What are you hoping your clothes are saying about you?

Jessica: I hope they say that I am a romantic, have class, enjoy vintage and learning about the past, and love to share my feminine side.

Deb: Anything else to add?

Jessica: I love hosting Turning Heads Tuesday, my weekly link-up with stylish, inspirational women. I also hope to continue my wonderful collaborations with brands that exemplify my look. Thank you so much, Deborah, for this interview!