Over 40 Style From A Girl in Boston

For Alyssa Romano, getting dressed is a joy.  That’s pretty obvious when you meet the woman behind Lissy in the City (A Girl From Boston.)

Scroll through her posts, and you’ll see dozens of photos of the perky blonde with the megawatt smile, happily showing off her latest looks. Clothes are Alyssa’s passion, and she’s been thrilled to share that with her readers for the last five years.

I recently had a chance to chat with this 40+ fashionista about her colorful, modern wardrobe. Here’s my interview with Alyssa (Lissy), my newest  Fabulous After 40 Styleblazer.

Deb: Lissy, Why did you start your blog?

Lissy: I worked in finance and was looking for a creative outlet to share my love of fashion and style. Plus, I really enjoy seeing what other real women are wearing and wanted to contribute to that.

Deb: How would you describe your style?

Lissy: What I love most about fashion is that I can represent myself and my style in different ways every day (one day ladylike, one edgy, another whimsical).  I like the classics, but every outfit has to have a unique detail (a stud, a bow, a pop of color).

Deb: How does living in Boston influence your style?

Lissy: Unfortunately, the main influence of living in Boston is the weather, especially in the winter.  I’m not one who favors practical dressing, but when it’s freezing and snowy out, sometimes there is no choice but to err on the side of practicality. I did splurge last year on a ruffle hem Moncler puffy coat to make me feel better about dressing for the bitter cold.

Also, living in a city where I walk everywhere influences my footwear choices, much to my chagrin. I used to be happy to prance about the bricked and cobbled streets of Boston in 4” heels, but I’ve become a bit more practical and now lean towards a lower heel, preferably in a block shape.  The bricks wreak havoc on a lovely kitten heel (which I wear anyway, but hey, at least I give my local cobbler lots of business!).

Deb: As a finance professional, you work in a professional environment. How does the fashionista in you inject creativity into your outfits while remaining office-appropriate?

Lissy: I’m lucky in that I work in an office that has a very flexible dress code.  Unless we have clients in the office, we can wear pretty much anything from jeans to a dressy dress. I generally like to wear what is considered professional clothing even though I don’t have to. I love a classic blazer, a fitted pencil skirt, and a tailored pair of trousers. But I add my extra oomph with fun accessories; bright shoes, lots of rockstuds, and bold baubles.

Deb: You say that getting dressed each day is a joy for you. Describe the elements of the perfect (or your favorite) casual outfit.

Lissy: My weekend casual uniform tends to be skinny jeans with an oversized top and either flat in the spring/summer or booties in the fall/winter. I’m smaller on the bottom than on the top, which is why I favor slimmer pieces on the bottom and oversized tops.  And in the fall and spring weather, where it’s still cool enough for coats but not so cold that you need a winter coat, I love to add a fun jacket on top.

Deb: Your wardrobe includes a vast collection of gorgeous high-end pieces. Where are your favorite places to shop for these items? Did you score deals on any of these pieces?

Lissy: My best friend Elisha is the personal stylist at Neiman Marcus in Boston, so I spend most of my shopping dollars there.  Elisha knows my style better than anyone, so she’s always got her eyes out for sale items that suit me.  I have a buttery soft leather moto jacket from Burberry that she plucked off the deep markdown rack for me. I also have a fabulous red fit and flare Jil Sander dress that came from the sale racks that I can wear three seasons of the year.  And I can’t omit the classic black Stella McCartney blazer that I got for less than half price.

I love shopping at Barney’s and Bergdorf Goodman when I’m in NYC. I also go to Charleston, SC, at least once or twice a year, and there is a super fabulous boutique called Hampden Clothing that I never miss an opportunity to pop into (you can also shop with them online). My favorite online shopping sites are Netaporter and their sale site, The Outnet.  They are the absolute best for giving you exact measurements in the description of each item which I wish more websites would do.

Deb: Can you offer some advice to women who want to build a wardrobe of high-end designers but are on a budget? Where can they shop? What are the best times of the year to score great deals?

Lissy: I think the Neiman Marcus last call sales have some excellent finds for high-end designer markdown items.  My advice is to develop a relationship with a sales associate who can keep an eye out for pieces that you want, as the good things tend to get snapped up quickly.

I also think the resale market is a great way to buy designer pieces for less. Sites like The Real Real and Yoogi’s Closet have fabulous products at reasonable prices, and you can trust that you are getting the real thing from them.

Deb: What trends do you love for fall 2015? Trends you know are not for you?

Lissy: Some of my favorite fall trends are those that happen to be a part of my regular style anyway.  One is capes; I have several capes in my wardrobe and have for years.  They fit my style since I like oversized items on top, and they serve a dual purpose of adding interest to an outfit plus giving me warmth when I need it.

Grey also seems to be everywhere, and I think it is a lovely neutral that works quite well with my love of color (you can pop it with accents of pink, red, green….just about anything). One of the trends this fall that I like but, in my opinion, is better in small doses is the Victorian trend. I think a Victorian blouse would be lovely with some distressed denim or a sleek pencil skirt, but I would personally stay away from an all-over Victorian look.

Deb: Everyone has fashion challenges. What is yours, and how do you get around it?

Lissy: I would say my biggest fashion challenge is dressing for my body shape. Being a size or two bigger on top presents its challenges.  I’ve overcome this by learning what works for me in terms of shapes and which designers fit me better than others.

Deb: So many women are afraid of color, but you do a great job incorporating it into your wardrobe. What colors are you most attracted to and why?

Lissy: Yes, I do love color!  I think I’ve just always been that way. I don’t discriminate when it comes to color (I love them all!), but for me, I more often go for the brighter colors (pink, red, kelly green) over the muted pastels. I find the brighter colors look better on my skin tone.

Deb: You seem to have a passion for shoes judging by the glass case full of shoes we see in your photos. Tell us more about that.

Lissy: Yes, shoes are a passion of mine. Even before I started buying clothing on the higher end, I always bought fancy shoes. They can make a less expensive outfit look like a million bucks. Plus, no matter how much the rest of your body changes, your shoes will always fit. I lived in a small apartment and was running out of space for my ever-expanding wardrobe, so I decided since some of my shoes were like works of art, why not display them!

Deb: I noticed that you use Poshmark to sell items that you no longer want? What is your most prized piece of clothing or accessory that you will never sell?

Lissy: This is a tough question. Years ago, I would have had a long list of things that I wouldn’t sell. But I’m learning to limit my emotional attachment to so much stuff, especially since I have limited space to store it all. Having said that, I have some jewelry (both real and costume) that were gifts that I would never get rid of (a diamond ring I got for my 40th birthday, a few Chanel brooches that were birthday gifts from my girlfriends over the years). And while I have sold a Chanel bag or two in the past, the classic Chanel bags I won’t ever get rid of. They never go out of style.

Deb: You’ve been blogging for a few years now. What has this experience taught you about your style or style in general?

Lissy: When I first started blogging, I was more apt to try things that, in many cases, weren’t the best for me. Experimentation in fashion is good, but for me, I have to remember to stick with what works for me and not to succumb to the temptation of trends that might be fabulous on someone else but aren’t the best for me.

Deb: Your advice to women over 40 who are struggling to find their style?

Lissy: Stay true to yourself. Nothing makes an outfit look better than a woman who carries it with confidence and a smile!

Deb: Anything else you wish to add?

Lissy: Thank you for including me! I love that you provide this outlet for women over 40 to get ideas and inspiration from each other.

Deb: Thank you so much, Lissy, for sharing your polished and colorful style with us. You are Fabulous!! Ladies, be sure to visit Lissy at her Instagram account @Lissyinthecity