I recently spent three days in Boston for a work trip.  So much fun.  It was a whirlwind but I was able to see lots of the city during my quick trip.  I had a few extra hours each day to explore this city I had been to several times but never really had an opportunity to enjoy!

I also did a fair amount of people watching (per usual) and my conclusion … Bostonians are stylish with a splash of practical.  There were two items of note in their practicality; their outerwear and their shoes. Those that live and work in Boston have commuting down to a science and it starts with their shoes.   I lost count of the number of cute flats I observed.  My favorites though were a gorgeous pair of all-over studded ones.  I saw the woman three times as I was strolling Newbury Street and wandering towards cocktails at the Four Seasons so I had ample time to drool.  I searched high and low and found lots of similar flats, but nothing exact!! #stillhunting

So what other fabulous shoes were on the feet of these stylish commuters? There were two styles that kept appearing again and again … mules and boat shoes!


Style Inspiration:  Glamour | Style Nine to Five | Posh Classy Mom | Bus Bee Style

I saw tons of mules.  I have typically thought of mules as rather impractical and not ideal for when you actually have to walk.  I’m going to have to rethink this based on the number of commuters I saw sporting this as their footwear of choice.

Mules That Might Make Me Reconsider

Sperry Top Siders

Style Inspiration:  Outfit Ideas HQ | Sperry | J’s Everyday Fashion | Fit Fab Fun Mom

The other shoe to note … top sliders. So many adorable options. You can even dress these up with a dress making them more versatile than you might think. And they come in so many fun colors!

A Rainbow of Sperry Shoes

Now on to outerwear. I will say one thing … Bostonians can layer. And layer with style … the two standouts? Moto jackets and trench coats.

Moto Style

My9to5shoes.com My 9 to 5 Shoes Moto Style Boston

Style Inspiration from  Elements of Ellis | Pinterest |  My Style Vita | Camille Styles

I love Moto jackets!  So much so that I have a black one and a grey one!  But ever since my trip to Boston I’ve been thinking I need one with color so I purchased a blue one during the Nordstrom sale. I saw so many stylish Bostonians sporting these fun Spring toppers paired with everything from dresses to denim.

The one I purchased is no longer available in blue but I found tons of other options!  (Black, Blush, Grey and Butter Here for $199!!! and Red Here and Silver Here!!)  I would recommend sizing up!!

More Motos

Trench Coats

My9to5shoes.com My 9 to 5 Shoes Trench Coat Boston Style

Style Inspiration:  Betty’s World | Just the Design | Be Daze Live | Fashion Gum

Classic. Perfect. Enough said. If you don’t own a trench … you have no excuse. So many good options. I rounded up my ten favorites and I also rounded up a handful of under $100 favorites (these are for you my Columbia Fleece wearing hold outs). #HasItsPlace

My Favorite Trench Coats

Trench Coats Under $100

What to Wear For Three Days in Boston

I was only in Boston for three days …. including travel and I managed to fit right in with my commuter, street style! First up … my casual travel sneakers. #SoPractical #SoPink

My practical twist for day two? Rothy’s on my feet in the street and in my tote when inside. (I wore them to walk the streets and switched to my heels once indoors.) #TipSavingTip

The last day was meetings and more travel. I changed into denim and my casual sneakers for the journey home but you can still see the buttoned up button down I had for my work look.

Where to Eat for Three Days in Boston

If you aren’t planning on eating seafood while in Boston then you should stay home. No seriously. #NotKidding

Island Creek Oyster Bar

Thanks for the fabulous recommendation from @FabLifeForever for this gem. Despite it being a night the Red Sox were playing I had no problem scoring bar space and enjoying every morsel. The biscuit cannot be skipped but then you must bring a dining companion because it was the size of my head.

North Street Grill

After a sight seeing early morning run and a quick change I grabbed a late breakfast, early lunch here. The food was great, the coffee was strong … but the bloody Mary’s looked even better.

Cocktails at the Four Seasons

After touring the shops of Newbury Street (and doing a little damage at Rag and Bone) I joined coworkers for martinis at the four seasons. #iconic


Dinner at Ostra was more seafood and fun! I highly recommend it!!

Tatte Bakery

Saving the best for last … I literally stumbled into this place while returning from a run along the Charles River. It was a good thing the run was included because this gem is full of indulgences.

Sight Seeing

By far the favorite thing I did was run the Freedom Trail. You could use the term run loosely because I did stop to see the sights and read some signs. And google trivial facts. #BestHistoryLessonEver

The trail is literally bricked (and painted) into the sidewalk so you cannot get lost and every notable sight has a marker where you can learn more.

I used my phone to learn more about each marker.   Things like the fact that the Battle at Bunker Hill actually took place at Breed’s Hill (apparent Colonel William Prescott was not the geographer yours truly is).

The run ended at the USS Constitution (where I did the full tour, including below deck). #SoCool #IDidAskThemToMoveTheCrane #NoLuck

This is one city I look forward to returning to as I’m not done with the seafood or the sights (or shopping)!