Weekend Style with Sperry

Weekend Style with Sperry | The Fresh Exchange

Just the other day I realized it is nearly Christmas and the last few days here have been closer to spring weather than Christmas weather. Though I love a good winter chill, these days are like gifts as I know at some point in the coming months we will be bundled up. With the weather being so wonderful we have been enjoying some favorite items a little longer than we normally would.

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Our weekend ahead is full of errands and getting things done for both the holidays and the list of things in preparation for life with a little one. This means we are layering up for the cool mornings and warm afternoons in order to tackle all the things on our to-do list, but the most important part is having a pair of shoes to keep our feet both warm and comfy through the busy weekend. We have been long time lovers of our Sperry’s for everyday wear. Growing up on Lake Michigan and spending my summers sailing we both have found that hands down Sperry knows how to make a great shoe for both casual wear and all day activity.

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Our pairs become very well loved, to say the least, but just like any great shoe, the longer you wear them, the better they become. So, when Sperry asked us to use their new custom boat shoe designer to make some fresh ones to give our older pairs a little break. It was fun to dream up our ideal boat shoe, and we both loved playing around with all the options. Have you ever designed custom shoes?

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

We cannot wait to wear them this weekend with our favorite laid-back layered pieces during these unexpectedly warm days.

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

Weekend Style with Sperry | The Fresh Exchange

What are your go-to weekend pieces? Do you have a favorite pair of shoes?

What I wore:
Cropped Trench from Everlane  |  Custom Boatshoes c/o Sperry  |  Black Maternity Skinnies from Gap  |  Chambray tunic from Lou & Grey

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What Mike wore:
Fleece Jacket from Ralph Lauren (Similar from Sperry)  |  Chambray shirt from Jcrew Factory  |  Raw Denim Jeans from Jcrew  |  Custom Boatshoes c/o Sperry

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This post was brought to you by Sperry. All thoughts and opinions are our own. Thank you for supporting the sponsors that all us to create all your favorite content on The Fresh Exchange every day. 

Leave a comment

  1. Do you have any tips for how to break sperry’s in? I Have one all leather pair that I Love love love the look of, but they tear my feet up. From experience with my last sperry pair, they are awful until they are perfect – but I can’t seem to stick with it through the pain in these new ones! Any SUGGESTIONS?

    1. Great question! I was just talking to Mike about this. They are a little bit of work to work in. I suggest wearing band aids on the back of your heels or anywhere else they seem to rub for a good week or so of wear. Also, if you are sure the shoes are the ones you want I suggest if they are leather boat shoes to get them wet in warm water. Since they are boat shoes they are meant to be worn in the water. Some people suggest doing a warm tub of water with salt water, but I think just water is fine too. The color of the leather may come out in the water a little, but it is okay. You place them in the tub with your feet in them. I have worn my other pair on our boat so often they get wet often so I haven’t had to do the tub thing, but I find this softens and loosens the hard and sharp parts of the leather so they can conform to your feet. A good pair of topsiders (Sperrys are truly the best) should last YEARS! My dad (58) still wears the first pair he got when he was 16. So don’t feel bad about getting them wet because they should stand up to it and open the water with open arms. If you want an exact process, I suggest googling breaking them in there are some good DIYS out there on how to do it properly. But if you live in a warm climate by the water I would just walk down to the beach and submerge your shoes and feet in the water and do it all natural 😉 If not the tub or shower is a great option as well!