CHS Debate: Boat Shoes, Yay or Nay

Apr 19, 2010

When I moved to Washington, D.C. five years ago, I was astonished by some of the fashions that residents of the Mid-Atlantic region consider stylish.

Your love of critter pants confounds me to a stupefying degree.  And your belief that plaid pants and brightly colored bow-ties are the preferred choice for formal occasions makes me want to gag.  But the most polarizing and divisive Mid-Atlantic fashion choice of all has to be the boat shoe.  

Some Washingtonians swear by them and love their Hyannis Port appeal.  While others insist that boat shoes are for poseurs, the prepster equivalent of the hipster favorite Chuck Taylors.  And the zeal with which each side articulates their position has always left me confused, wondering what side I’m really on in this debate.

So when frugal fashion guru The Cheap Chica featured the tasseled moccasin as one of this season’s hottest trends, the explanation she gave for her blooming adoration only deepened my consternation about the boat shoe.

OK, so they’re not the most attractive or sexiest pair of shoes out there and they totally remind me of something my father would wear, but they’ve appeared in every fashion magazine from Glamour to Lucky and they’re starting to grow on me!

She admits that the shoes aren’t attractive or sexy, and that they look like something an AARP recipient would wear, but then she sidesteps her entire argument and asserts that all of that can be overlooked because fashion editors love them. 

This, of course, prompts the question: If the editors of Lucky wear Crocs, will you wear them too?

Granted, boat shoes aren’t as far down on the Faux Pas Scale as Crocs.  But I just don’t understand the appeal. 

I’m willing to accept that this could be a lingering geographic prejudice.  After all, I grew up surrounded by cowboy boots not deck shoes.  Yet, I wonder if my confusion means that I should be more accepting of this regional footwear selection or if I’m justified in my dislike but feel unsure because I’m in the minority.

Thus, I decided to toss this question to the masses and ask you, my loving readers to help me decide: Are boat shoes preppy chic or totally weak? I look forward to your comments.


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  1. Belle says:

    Bianca consider yourself today’s blog comment superstar.

  2. Belle says:

    Bianca consider yourself today’s blog comment superstar.

  3. t says:

    thumbs down on boat shoes

  4. Samantha says:

    Despite being a native East Coaster, I wholeheartedly agree with Belle. Just say no to critter pants, madras, and boat shoes, even if you’re on boat.

  5. Maggie says:

    Whoa, whoa, whoa. Belle, normally I think you are spot on, but I think you’ve missed the boat (ha! I made a pun!) on this one. I, too, am from a geographic region where cowboy boots are the norm. But, living in a part of the country that is home to many large bodies of water, from lakes to oceans, I also grew up around boat shoes. I happen to love them; worn with a polo and khakis for the gents, or with a cute pair of shorts and tank top for the ladies. What ruins them is the same “faux-preppy” set that swears by critter pants and popped collars. Talk about poseurs! Take safari-style shirts, for example. If you’re actually on a safari, or happen to be in Africa, I’m all for them. If you’re in DC, you look like an idiot. I feel somewhat the same way about boat shoes; if you’re around/on the water, they are perfectly acceptable. If you’re at work or out to dinner, then no way.

  6. Maggie says:

    I should add that you have chosen a truly unfortunate picture of boat shoes to display. You can’t go wrong with a classic pair, such these:***7********9102047*M090&productId=7-134400&catId=cat90048DM

  7. MAB in VA says:

    I think boat shoes are adorable! some of the “sky high heels” that are this season’s top trends are what confound me

  8. KLo says:

    I have to +1 Maggie. I love boat shoes with shorts. I hate critter pants. And popped collars make me want to scream. (RVA is home / I’m an Alabama resident … for about 13 more months.)

  9. A says:

    I bought my Sperry topsiders (traditional light tan leather) at the end of last summer at the boater’s store less than a mile from my parent’s lake house. I have to admit my purchase was inspired by my weekend on the boat but I have definitely enjoyed the shoes since. I did pack them away for the winter and have just recently brought them back out. They were the perfect shoe for my recent trip to Orlando. Walking around Disney and Universal all day required a comfortable shoe and sandals were out as they would limit my choice in rollercoasters! My boat shoes were absolutely perfect and a great accessary to my semi-nautical themed outfit – Banana Republic shorts (white) and navy ruffled tank (Loft).

    However, I do not believe they should be worn in any sort of formal attire. A few of my male coworkers will wear them on “business casual” Friday but I feel that they are way too casual, especially when women really have so many cuter options for a “casual” show.

    Lastly, the seer-sucker, boat shoe, Ran-Ban look just makes me sick. Sorry Belle, but I feel that is a common Hill staffer offense. Make it stop!

  10. Anna says:

    In college (SEC School), I went a little crazy and bought too many pairs of boat shoes. The Authentic Originals, the backless slides, dark brown Angelfish and even a madras pair. Now that I’m a little older, I’ll reach for a feminine ballet flat instead of Sperry’s. My wardrobe has matured, and I just don’t have as many boat shoe opportunities now as I did back in college.

  11. janae says:

    Are you kidding? Boat shoes are quite fashionable and Gucci made them iconic. Boat shoes are amazing and especially a great way for men to branch out in fashion. They could easily go from casual to upscale IMO.

  12. a says:

    Boat shoes are timeless, esp the classic brown with white bottoms. Love them. Had my last pair for 5 yrs, regularly got compliments on them – even in the midwest. I think the cowboy boot comparison is apt – those are also timeless but more appropriate/common in the south and west. And like cowboy boots you need to be mindful of what you wear boa tshoes with so you don’t look ridiculous

  13. b says:

    Boat shoes are just awful and I’m thrilled they’re finally being called out!

  14. District Cut says:

    This will always be a debate in a city like DC where there are people from all over the world. It’s all relative to where you are from, but generally speaking I think they are a part of the DC and East Coast culture. I mean, Ive always worn them when going down to the Chesapeake Bay or Martha’s Vineyard during the summer time. Not to mention they were perfectly acceptable when I was in school, they complimented my uniform quite well. But I think we can all agree that they are a hot trend in menswear right now, and are classic Americana. So many designers have put their spin on the boat shoe and have accepted them as an iconic piece of fashion. And there are so many different varieties, I’m sure everyone can find a pair they love. Check out a few of the different options for menswear available for this season

  15. steph says:

    I like them 🙂

  16. Bianca says:

    They ask you to turn in your rights to use your southern charm and deny you sweet tea if you don’t love boat shoes in the south.

    I love them, and look at it this way….boat shoes are a great alternative to wear for occasions that require a lot of walking and beat the hell out of tennis shoes!

  17. Chelsea says:

    I think boat shoes are incredibly ugly. Sperry’s are an eyesore.

  18. I’m from the Midwest, where boats & the shoes that go with them are unheard of. But I have to say – I love them. They’re so yuppie, so “Let’s head to my yacht.” They’re comfortable, often colorful, & I really don’t think they’re ugly. Give me boat shoes over four-inch heels any day.

  19. Belle says:

    Bianca consider yourself today’s blog comment superstar.

  20. Rory says:

    I grew up around boat shoes in the South, although I didn’t get my first pair until college (anybody else remember the whole “fratty” thing?). Up until then, only guys wore them. My Sperry’s are so comfortable I’d exercise in them if it wouldn’t look weird.

    But I love madras, am okay with critter pants (on toddlers and old ladies), hate the popped collar. That was never Southern.

  21. Lexi says:

    While I can understand Belle’s disdain for boat shoes as a fashion trend, their practicality cannot be understated. Wearing Sperry’s while out on a boat is natural, they give you the grip on the deck and with the various styles and colors, they are able to transition easily when back on land (when stopping off for a quick drink or bite to eat). Down at the Georgetown Waterfront, seeing Sperry’s is pretty common and forgivable…but that excuse doesn’t work when you’re exiting metro and heading up the sidewalk to the hallowed halls of Congress. At the end of the day, style is subjective, but common sense isn’t!

  22. Allison says:

    I love boat shoes as well, and I definitely grew up in the land of cowboy boots and wranglers. Sperrys are practical! Your feet don’t get too hot, you can walk around in them comfortably, and then are a plain tan color that is easily matched and unobtrusive. In my opinion, the rule is to keep them clean and tidy. I wear a pair out pretty much every summer, so I get rid them out when they get ratty.

  23. District Cut says:

    So do you guys feel the same way about loafers than? Because Gucci loafers look quite similar to some of the boat shoes on the market today.

  24. CatG says:

    The problem isn’t the boat shoes, the problem is the d-bag contingent that popularized them. (No, not everyone who wears them is an insufferable waste of human flesh, but they do make up a substantial proportion of the boat-shoe wearing demographic). Why is that?

  25. Jill says:

    I bought these last season, thinking they were more feminine than the traditional top-sider but still had a preppy look. Like the look of the shoe. Unfortunately, they’re extremely uncomfortable. I think the traditional version looks better on men than women.***7********9762352*M060&productId=7-132460&catId=cat90048DM

  26. firecracker says:

    absolutely love them. i’ve been wearing them pretty consistently my whole life. they’re practical, comfortable, and go with all things casual. what else does a girl need?

    to be fair, i grew up riding horses and sailing, and i’ve been known to wear my cowboy boots and my boat shoes at inappropriate times.

  27. Jessica says:

    I own a pair of dark brown sperry’s to wear on low-key sundays, and when wearing sneakers will make me feel like I’m 15. My boyfriend also owns a pair, and when we’re going out to eat for a casual dinner or lunch, they look SO much better than his nikes with jeans.

    My thoughts in general on them: They dress up a pair of jeans or dress down a pair of khakis. Nothing more, nothing less. They’re comfortable (mine are waterproof) and are definitely not hideous.

  28. Maggie says:

    As a Southerner, I still think boat shoes should be a staple in any lady’s summer wardrobe. However, I agree that popped collars are an eyesore, and I’m a bit offended that someone (anyone) would consider them a Southern trend.

  29. Vicki says:

    I say wear them to commute, because they’re alot cooler than that abomination of reebok high tops and socks alot of women in DC still wear on the Metro. Then when you are on your way to that job that pays too little and gobbles up all of your free time you can at least look at your feet and dream of the day you have enough free time and $$ to actually wear the shoes on a boat. Personally I like them on guys IF they’re broken in without being worn out, worn w/o socks and worn with jeans and a blue or white button down. Casual Trad, vs affectation Trad a la critter pants/popped collar.

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