five outfits

1 Girl, 5 Outfits: Elsa Massey

I’m extra excited about today’s 1 Girl, 5 Outfits post because it’s by my new friend Elsa. We met a few months ago after I moved to the suburbs. We reached out to each other via DM (I’m not sure if I did it first or if she did) and then got together for a “friend date” at a local coffee shop that lasted for, like, four hours. We immediately hit it off and clicked as friends. I can’t tell you how grateful I am for Instagram because it totally brought us together!! I was also super excited to hear that she was planning on launching her own blog (just launched last week) and knew I wanted to have her share a week’s worth of outfits. She’s got great style– that I know you guys will love– and shares her size-inclusive finds!


Hello! Elsa here. I am a 28-year-old native of New Jersey where I reside with my husband, Andrew. By day, I am an assistant at a private wealth management firm in New York City. By night, I am the voice behind @simply_elsa, the Instagram account where I focus on size-inclusive classic style with a little preppy panache. I love to entertain, decorate my home for the seasons and co-author the blog Purely Simply with my sister-in-law! My passion for decor and entertaining goes way back, I have my Master’s Degree in Decorative Art and used to be a buyer for One Kings Lane (my love for blue and white runs deep!). When I made the career switch into administration I found myself searching for a creative outlet and, in my free time, began pouring my heart into my style Instagram and blog.

Style is something that I never struggled with, but shopping was. I knew what clothes I loved, I  just could never find them in my size. So, a few years ago when my weight began to change, I started searching for size-inclusive preppy brands that would help me keep my classic style. The style that truly felt like me. I’m in that grey area where I can usually wear a straight size XXL or a plus size 1X, which has made things a bit challenging. Something I have learned through this is no matter your size, you should never have to compromise quality or style just because you don’t have a certain build (and this applies to everyone). When I started to embrace my body my natural style came out so fluidly and, after a lot of trial and error, I found that I did not need dozens of brands to choose from, I just needed the right ones. 

 As I’ve gotten older, my style that was once seersucker dresses and statement necklaces has evolved into a more “tailored” preppy, consisting of navy, neutrals, pops of animal prints, and polished silhouettes. All completely achievable in both straight and extended sizes.  When Carly asked me if I wanted to do this post (it was an immediate YES), I knew I wanted to show practical outfits that I find myself wearing on a regular basis. So, I have styled five easy and elevated looks that I hope to inspire you to style your life regardless of your size! 

J.Crew Chiffon Top, J. Crew Curvy Fit Toothpick Jeans, Chanel Ballerinas

I work in the finance field and while I am able to wear denim to the office, I must always look put together and tidy. This easy outfit is from J. Crew! The smocked collar blouse is so comfortable, barely wrinkles and looks super polished while feeling like you are in pajamas. I pair it with J. Crew curvy fit denim, which I swear by, and my Chanel flats. My Chanel ballet flats were an investment and I definitely wear them more than any item I own. Any cap-toe flat, Chanel or not, has a timeless look that is sure to elevate whatever outfit you pull together. I love to put on this look when I want to be comfortable or might have plans after work, it is easy and transitions from day to night.

Tuckernuck Easton Blouse, Eloquii 9-5 Work Pant, Margaux NY Classic Flats, Cuyana Classic Leather Tote Tuckernuck Birdcage Earrings (c/o)

This is my tried and true look for days where I do need to wear “work pants.” It is simple, chic and versatile pieces can be mixed and matched with other items. I love this outfit because you can easily swap out the pants for a pair of denim and make it work, too. Boy oh boy do I LOVE this blouse from Tuckernuck. Tuckernuck recently extended their size range to include XXL and, while it is not a true plus size, it is a great place to start and I find their blouses to be fantastic.

The Eloquii 9-5 pants are my favorite dressy pants, they have an elastic band in the back and are tapered so perfectly for my curvy body type. You can also select your inseam! That is huge for me. I find that I wear these pants in and out of the office as much as I do denim! I paired them with my Margaux NY leopard classic flats and Cuyana tote which are both workhorses in my day-to-day wardrobe.

3. J.Crew Leopard Dress, Similar Talbots Heels, J.Crew Satin Turban Headband

I am a firm believer that every woman should have a dress in their closet they can throw on for any occasion and feel great. This is that dress! I have owned it for a little over a month now and I have managed to wear it to the office, an engagement party, a wedding and out on date night. I styled it with fun and simple accessories and every time I wear it, I switch them up to give it a slightly different look. The simple turban headband is an understated nod to the hair accessories trend and these Talbots pumps (c/o) have the most adorable tortoise heel!

4. Dudley Stephens Cobble Hill Fleece, J.Crew Curvy Fit Straight Leg Denim, J.Crew Sadie Ankle Boots, J.Crew Western Hat

We are in the thick of Fall and this outfit has definitely become my autumn weekend uniform. Living in the suburbs I find myself traveling near and far to run errands so comfort is key. Whether I am grocery shopping, getting lunch with a friend or pumpkin picking, this look seems to work for just about everything. I have a few Dudley Stephens fleeces and I have to say, the Cobble Hill is definitely my favorite! DS goes up to an XXL or 18/20 (which I am wearing here) and the longer length of the Cobble Hill is definitely their most figure-friendly option for tall or curvy gals. I paired it with yet another pair of J. Crew curvy fit denim, these fun J.Crew leopard boots, and a camel hat.

A good blazer is a must! I am big on blazers, they are so versatile and can transform any outfit. I find myself wearing this Madewell blazer and bodysuit combo on a weekly basis. Madewell, like J.Crew, has increased their extended-size options and they are all really good. I recently wore this look to a brunch and felt so put together, when in reality I was just in a t-shirt and jeans! Since I do spend 5 days a week in the office, I like to find pieces that can be worn both in and out of the workplace and everything here meets that criteria. I dressed up the combo with the same pair of J.Crew jeans I styled with the polka dot top, and added my Stubbs and Wootton slippers. I love a good smoking slipper! They are so old school and polished look fantastic with jeans.

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Allie N.

Elsa, thank you so much for sharing! Your style is so classic and put together. I’m definitely coming back to this post for outfit ideas.


Absolutely love your style Elsa! The jcrew toothpick jeans have never fit me very well (I keep trying them on every so often as so many people love them!) but I didn’t know they had a curvy version and now I feel like I definitely need to go try them on. Thanks for the idea!


I really enjoy this series, 1 girl 5 outfits! It’s so great to see what others are wearing across the country. I love this post in particular because it highlights body positivity and styling for the body you have! I love that she included brands that Carly often wears, and shows that style isn’t just for skinny people, it’s for everyone! These are great outfits, I love that they can be transitioned from work to going out or even just running errands!


Loved every single outfit! It can be so hard to walk the line between casual and put together in the work place and she totally nails it. Thanks for sharing your amazing style, Elsa!


Yay!!! I love Elsa!! She has incredible style that has convinced me I needed a pair of jeans after going nearly 10 years without wearing jeans!! Thank you, Elsa!! This post is amazing!! Also, like maybe a Jersey friends meet-up?!

xx Libby


Love all of these outfits, and I love seeing a plus-size influencer in the preppy world!
Also, would love to know where the necklace in the last outfit is from? I didn’t see it linked


Love this! Love seeing a range of body types and a Clear discussion of sizes. The outfits are PERFECTION.


I’m usually not a fan of this series but for this post I make an exeption. I love every single look and already thought about how to recreate them at home. Elsa really is a beauty and has a great sense of style!

Courtney Jenney

I absolutely LOVE following along with both of you two (Carly and Elsa). You both have incredible style – and it’s so great that you’re able to use your platform to make sure all women are finding clothing that makes them feel their best!

christina villecco

This was my favorite! Id wear every single of these looks head to toe! Awesome style and Ill be a new follower of Elsa’s!


Thank you, thank you, thank you for sharing so many great plus-sized options for REALLY stylish clothes!


Ooh I want that madewell bodysuit/blazer combo! And I’m inspired to buy more headbands. Love these outfits.


Holy smokes, these looks are terrific!! Elsa, everything you put together is just golden. I hope to see you more on this blog in the future!!

Christina Marie

Holy goodness, that last outfit is so ridiculously flattering! It’s absolutely perfect, and I’m going to have to steal it immediately. The shoes are the perfect amount of pop to an otherwise neutral color palette.


Thank you for this one, Carly and Elsa. I related to it so much, as my body has really changed since having a baby 6 months ago. Learning — slowly — that I can still wear what I love in this new body. Thank you for the needed reminder!

Mary Kate

Wow love all 5 of these looks! I can see myself wearing them all, but omg that leopard dress..!!


I love these outfits! As I’ve gotten older, I’ve also found myself reaching for more neutrals, and all of these are outfits I could see myself wearing.

Ashley Snelgrove

I’m so glad you featured Elsa!! She is one of the very few classic, preppy bloggers in the mid to plus size range. It can really be a challenge sometimes to find quality items for my size and she always does a fabulous job of sharing size inclusive options.


Hi Jennifer! I am 5’6 and they hit ankle length for me. I think these are more of a fall/cool climate pant vs. winter, just because ankles are exposed. I hope this helps!

Tara N

I think every outfit was just cuter than cute! Elsa, you’re so photogenic. Thanks for the inspiration!

Victoria Brazell

You, Elsa, have easy, effortless style…. Chic, eye-catching, confident!!!! One can see that style is inherent in you.


SUCH a beauty!!! I really appreciate the thoughtful, well put together descriptions of the outfits…thanks for having her, Carly!


Elsa, you are gorgeous and your style is impeccable! I love that you wear a lot of neutrals with some patterns splashed in. Can I be you?


I absolutely love this post! As a size 18 who has been trying to incorporate a prep/modern take into my wardrobe for years, it means so much to see someone else doing it so well and so thoughtfully. Will definitely be following Elsa too from now on! Thank you Carly, for this awesome series!