Meet Maria Osborne: Shoemaker, Saleswoman And Sea Lover

Each month, we spotlight one of the shoemakers behind Rockport. This month, we’re excited to introduce you to Maria Osborne. Read on to learn more about why Maria loves working at Rockport and how she spotted a Great White off the cost of New England this summer (photographic evidence included). 


My job at Rockport is…Territory Manager

A day in my life at Rockport looks like…Right now, I’m selling in our Spring 2018 line. I always have between five and six shoe sample bags in my car. My accounts are mostly family owned independent stores in New England. When I’m on a sales call, I travel to the stores and set up my samples like a mini pop-up store. I meet with the buyer and we review the current business and then work through the new product line. We work together to select the right assortment for their customer for that season.


A little snow didn’t stop Maria last winter. Here she is in NYC with her shoe bags, ready to show the latest collection.

My favorite thing about working for Rockport…Being able to have a voice, not only for me, but for our customers, is a unique thing about my job. Our product team does a great job reaching out to us to get our feedback from the field. It’s this kind of teamwork that helps us produce the best products in the marketplace.

Also, some of the friendships I have made. Having great people to call my “Work Family” is very important to me! When you spend most of your life on the job, it’s nice to have co-workers who you consider family.

A few of my favorite styles from this season…I love our Hattie collection! The insole is loaded with cushion and feels like you are walking on pillows. The leather uppers are extremely soft and really mold to your foot. The styles are right on trend and I always get compliments when I have them on.


Pictured: Cobb Hill Hattie Cuff Hi Vamp ($110)Cobb Hill Hattie Gladiator ($110) | Cobb Hill Hattie Lace Up Sandal ($110)

A trend I’m currently digging…Athleisure. When I’m not on the road, I’m an active mom. Playing tennis, heading to one of my kid’s soccer games or just hanging out with the family. This trend really fits my lifestyle right now and the footwear designed to go with it is fun!


Pictured: TruFLEX Tie Sneaker ($120)TruFLEX Lace-to-Toe ($120) | Raelyn Knit Tie Sneaker ($69.99)

During the week, I also enjoy…Beach and boating with the family. We love being on the water and feel fortunate to live so close to the shore. Every summer we make a boating bucket list of places we want to visit or things we would like to see. This summer unexpectedly started off with a Great White Shark sighting! It was a calm day on the water and we were able to cruise alongside this beautiful and scary creature for at least 100 yards. Wasn’t on the list, but certainly made it to the top of our most memorable moments!


The people who inspire me…My parents have raised eight kids with many challenges. They have taught me to work hard, don’t give up and family is forever!

 A quote that inspires me daily…“Live life to the fullest.”

In five years, I see myself…Personally, sending my kids off to college – yikes! Professionally, enjoying the success of The Rockport Group. I have more than 18 years of experience in the footwear industry, working in many different roles along the way. My hope is to utilize all of my knowledge to be a leader and major contributor to our company’s continued growth, whether it be here domestically and/or internationally.

Fall Change-up: Chukka Boots


As summer starts to cool down, but the outdoors still beckon, it’s time to reach for the fundamental transition shoe we all know and love: the chukka. Kick start your fall wardrobe with one (or all) of these three styles that are sure to become a staple in your late summer and fall (and let’s be honest, winter and probably early spring) wardrobe. Your ankles will thank you.

A Classic Re-imagined. The Wynstin Chukka Boots are for the guy who appreciates old-school charm and values modern-day comfort tech. Handcrafted details with vintage-feeling leathers kick this classic up a notch, and a removable Ortholite® footbed will keep you cool and comfortable all day long. Wear them with anything from rugged shorts and a classic tee to dark denim and a sport coat.

wynstinWynstin Chukka ($130)

Dapper Details. Elevate your everyday uniform with the Style Purpose Perf Chukka. This boot can be paired with anything from a refined suit to simple jeans and a tee. Perforated uppers in full grain leathers add a dash of detail while a padded collar and EVA heel cup provide a soft, secure fit.

sp chukkaStyle Purpose Perf Chukka ($130)

Rain? Check. The Essential Details II Chukka is your secret weapon for a rainy day. With waterproof leathers and nubucks, these bad boys will keep your feet dry and polished all day long. The cognac color aptly complements the warm hues of fall, or grab them in black to pair with your work suit.

EDII chukkaEssential Details II Chukka ($115)

Check out more chukka styles, in an array of colors, materials and designs, right here.

How to Rock: Our Hattie Sandals


Comfortable block heels, fashion-forward silhouettes (think: gladiators, lace ups and slings), and neutral, wear-with-anything colors are the hallmark of our Hattie Collection. The Hatties are a must-have for your wardrobe this season and next, as their chunky heels transition from summer to fall without a hitch.

We paired the versatile Hattie sandals with some of our favorite looks that keep you on-trend for whatever lies ahead, whether you’re planning a late summer beach getaway or looking to step (comfortably) into fall. Here’s a look at a few of our favorite ways to style the Hattie sandals for every occasion, from work to weekend.


Ring Necklace | Sunglasses | Dress | Denim Jacket | Planner

Keep it chic and casual with the Cobb Hill Hattie Gladiator. These trendy suede sandals up your gladiator game with some added heel height but keep you cool and comfortable with breathable cutouts and supple cushioning. For an early fall day-to-night look that can seamlessly take you from your desk to drinks after work, pair with a sundress, denim jacket and a suede fringe shoulder bag.



Earings Necklace Phone CaseBracelet Clutch Jeans | Top | Jacket | Belt

The Cobb Hill Hattie High Cuff Sling in blue adds a subtle pop of color to any look, whether you’re dressed up or dressed down. For dinner or a night out on the town, we love these sling-backs paired with white jeans and a ruffled top for an effortlessly on-trend look. When the weather starts to cool and the seasons begin to change, add a beige leather jacket to take this look from summer to fall in a flash. Looking for a more neutral, wear-with-everything hue? Try the Hattie Cuff High Sling in this gorgeous tan.


Shorts | Top | Bag | Sunglasses | Zip Pouch | Coin Purse | Bracelets

Though summer is slowly coming to an end, the heat is still on, so here’s one of our favorite looks for last-minute beach trips. Think versatility in these two-tone nude suede Cobb Hill Hattie Lace-Up Sandals. Mix and match with denim shorts and an airy tank for a laid back beach vibe or pair with a lightweight maxi for an easy, breezy look. These lace-ups feature a molded foot bed to provide complete comfort, which makes these chunky sandals a footwear staple for a casual coastal getaway. The Hattie lace ups are perfect for long walks and whatever else you have planned (or unplanned) for a weekend away by the sea.

See the full Hattie collection here.

Looks We Love: Wear-With-Anything Wingtips

wingtip-blog-header-2 (1)

From day to night, weekday to weekend, wingtips can be the perfect shoe for any occasion and every season. This classic and versatile shoe will keep every on-the-go guy comfortable for hours on end, from the heat of summer to the chill of winter. Take a look at the many ways to wear wingtips year round by checking out some of our favorite looks below.


Summer: The Wyat Wing Tip Oxford is as comfortable as it is stylish, featuring both a plush foam footbed and amazing detailing. We love Brick & Vine blogger, Ryan Rosenkilde’s clean and classic summer look with wingtips, rolled jeans and a button down, perfect for a date or casual day at the office. Step up your warm weather weekend wear by dressing down dark leather wingtips with shorts and a lightweight short sleeve button down.


Fall: Update your fall footwear by pairing wingtips with bold polka dot socks. We love this polished look by menswear-enthusiast @Drmmathias featuring the Wyat Wing Tip Oxford. Roll up your jeans to show off your shoes, and pair with a relaxed button down and vintage luggage for smart travel style, fit for crisp fall weather. The memory foam footbed of these wingtips make this shoe the perfect travel companion to take you where you need to go with ease and comfort.


Winter: As temperatures plummet, pair black leather wingtips with neutral, dark tones for an understated winter look. Roque and Soul blogger, Carlos, adds a sophisticated edge to his street style by wearing his Marshall Wing Tips with a minimalistic outfit while sightseeing in Austin, Texas (read more about Carlos and Jenna’s Austin adventure with Rockport here).


Spring: The Jaxson Wing Tip is the wear-with-everything dress casual shoe you need for spring. Matt, the husband of Visions of Vogue blogger, Jenna Colgrove, looks ready for warmer weather by pairing his wingtips with a yellow polo and dark jeans for a date with his wife. The red laces of this classic, versatile shoe add a hint of modern to every look while providing complete support.

How will wingtips make an appearance in your closet this season and beyond?