Hannah Osterman

IMG_0116editedHannah Osterman hails from Nebraska, graduating from Iowa State University with a degree in apparel design.  She did an internship with Coldwater Creek in Sandpoint Idaho and got hired before migrating to New York on a job transfer, switching from product development to design.  She now designs for Talbots and writes fiction for fun.  

What type of trip is it? To visit my sister since I do not visit her enough.

Destination? Chicago, Illinois

How many days? Four days.

Any travel buddies? My book.

Local weather is like… warm/ chilly/ cloudy/ sunny and unseasonably not humid.

What’s the packing strategy? See what’s clean and fits into the carry on! For this trip I’m planning the outfits based on activities. I have a “Chicago” tee for the Cubs vs. Mariners game, an easy eyelet woven tee for Rib fest and a swimsuit in case of having time to lie out by the lake!

How many bags and suitcases? One purse and one carry on.

Are you checking in or carrying on? Carry on! Since my four days worth of clothing fits into one bag I figure I’ll haul it on with me to avoid waiting at the baggage claim!

Do you use any travels aids? I have my iPhone, wallet, hairbrush, lipstick and earphones.

Do you use any travel apps or checklists? My sister sent me a reminder e-mail with a checklist of what I needed to bring, including: umbrella, swimsuit, Cubs tickets, and my excitement. I also use the Southwest Airlines’ app for checking-in and tracking my flight status.

The book you’re bringing is This trip I am bringing “Wait For You” by Jennifer Armentrout. I got a signed free copy of the book when I attended Book-Con. It is a cheesy romance novel…

Are you a prep packer or last-minute type? I am last-minute all the way!

Never leave home without…my glasses and a contact case. My father always texts or e-mails to remind me!

Any rituals or guilty pleasures you do? If I have an early morning flight, I generally do not shower but instead opt for a hat and sunglasses. My shabby lets me get in more shut-eye!

Have you ever missed a flight? I haven’t missed one… but I have gone to the wrong airport (only in New York) and let me tell you, I probably aged seven years that day.

Any tips for fellow travelers you find helpful? When going to Chicago, prepare for any and all-weather. Wear good walking shoes and aim to look Midwest-fabulous.


The outfit strategy–airy and cheery. A bright lip (stick) or two, beads, Converse kicks, eye contacts, hair-brush, medium rinse denim jeans, hot pink umbrella (you never know), glasses for the inner owl, iPhone and charger, linen slub mini-emergency kit, reading material, shades, wide brimmed straw hat, white eyelet top, reflective silver Birkenstocks, sports jersey tee and striped zip bag.


A few of her favorite things on the mantlepiece.

Be the first to comment!