Do or don’t: Boat shoes this fall

What kind of shoes do you wear in the fall? I usually wear flats, but I’m hoping for a new look. So I was psyched to see these boat shoes on Tomboy Style. They’re cool and tomboy-ish, and I’ve spotted super chic women wearing them around New York. Thoughts? Would you wear them?

From top: Bass, $119; L.L. Bean Signature, $69; L.L. Bean, $49; Bass, $119.

(By the fantastic Tomboy Style)

  1. Anonymous says...

    I love boat shoes! Pictured, however, are moccasins or blucher mocs. Boat shoe, blucher moc, and camp moc are not interchangeable terms! (Uh, says the preppy New Englander who grew up 15 minutes from the L.L. Bean flagship store.) :-) (…And who also just discovered your blog and is reading and commenting on old posts.)

  2. I’ve seen them in a bunch of stores lately and am in love! I’ve gotta say, you’re the first blog I’ve seen them on, though I have been way too swamped to read many blogs. Way to be spot on!

  3. I love boat shoes! Of course, being in North Carolina, I never realized that they weren’t previously “in style”. I’m pretty sure I wear them through every season. Go for the good ole sperrys! Classic, and super durable!

  4. i’ve been wearing these awesome sebago boat shoes i picked up at a thrift store in north carolina last week every day since i’ve been back and love them! (ps hoping you can make it wednesday night!)

  5. Well boat shoes are really something for someone with a particular type of taste. I personally can’t see myself wearing them but if they came in pink then I may try it out!

  6. i think they’re so cute. i’d just be scared of the awful stinky feet that must come from them, but i guess flats do the same thing. so go for it :)

  7. I love boat shoes. They are so comfortable! However I find it quite difficult to match them with my outfit sometimes. Too boyish to go well with skirts/dresses and they are getting quite common these days.

  8. super cute! I also want to get some moccasins. Unfortunately, it rains a lot in the PNW so cute shoes are rarely worn. :(

  9. I bought my husband some of the Timberland boat shoes for his bday so he’d have something to wear to work with long shorts.

  10. Yes to boat shoes! But, NO way in the fall (past September)! These are summer only shoes!!!

  11. Anonymous says...

    I bought a pair of Sperry topsiders this summer, and I don’t even care if they’re cute. They are. So. Comfortable. I live in them now!

  12. I would, IF I was living somewhere cooler…
    Here, in Cyprus, it’s sooo hot no one is able to tolerate shoes over sandals, long trousers away from an air-conditioned area etc…
    So, not much of a choice…. :p

  13. I wore shoes like this growing up with my school uniform. Adorable! Ive been thinking penny loafers too!

  14. They’re not for me. I am into shoe boots this season. In fact I already have two pairs from last season and new pair I picked up already for the coming season.

  15. Do! At the beginning of summer, I got a pair of Sperry Topsiders in the most perfect shade of gray from J.Crew. I love them! I live in SF, so I needed shoes that were comfortable to walk everywhere in yet more stylish than tennis. They were the perfect solution.

    I’ve also gotten a couple of pairs of the colored loafers from Bed Stu that Anthro is selling. I’ve been wearing those all the time too.

  16. Personally, I’m dying to get my hands on a pair of oxfords, but I like these boat shoes as well!

  17. I bought the cutest pair of blue plaid boat shoes from Payless and I have been rocking them all summer at work with pencil skirts and such. I love boat shoes!

  18. Do, great brand called Dubarry from Ireland, handmade and absolute musts for the a/w ahead!

  19. I love my Sperry’s! Definitely get a pair! They’re good for rainy days when you don’t want to wear flip flops or wellies too.

  20. i used to wear these as a pup with curlicue laces, remember them?

  21. Definitely a do. I have some Sperrys (I know, I know, I am such a follower) and they are awesome.

  22. Sarah says...

    nope, not for me. I’m not a fan of manly shoes on women. I had a pair similar to those when I was in middle school (or maybe high school?), but I wouldn’t wear them now.

  23. They’ll surely look great on you–do it!

  24. i can definitely see you rockin those shoes but for me, no way…

  25. Do! With slouchy trousers or skinny jeans. Simple and classic.

  26. there are some really good vintage boat shoe options on etsy, too! :)

  27. do do do!! so adorable! all of the bridesmaids (including me) for my friends wedding are getting similar shoes. so excited!

  28. Anonymous says...

    I wore Sperry at University in the (80s!!) yikes! So I’m going to pass on this retrend and stick with my ballet flats

  29. I have a pair of sperry shoes and i love them till no end, so cute & so comfy!

  30. An absolute DO. But only if you go with Sperry Top-siders. Any other brand/pair/attempt is a falsehood! I’ve worn mine every summer for 8 years. They’re incredibly comfortable and perfectly worn in.

  31. C. says...

    YES definitely! I love the tan pair.

  32. Oh, also — I am pretty strict about this — only Sperry Topsiders, and only LL Bean bluchers. Original, classic, no substitutions.

  33. I love Topsiders, though I am somewhat dismayed at how pervasively trendy they have become lately, and I would definitely consider bluchers like you show, but I am pretty sure I only like them with shorts or cropped pants, so they are really a summer staple for me, and not something I’d wear once the weather started requiring socks…

  34. Mallory says...

    I’ve worn the same Sperry Topsiders for 5 years now, and they’re STILL holding up. They’re super comfortable and match everything. I love them. DO! DO! DO!

  35. Yes, I love boat shoes. I have a hot pink pair from a few years ago I absolutely love and will continue to wear until they fall apart!

  36. Foteini P. says...

    Love them!!!! :)

  37. v. says...

    they are a great go-to summer shoe. and fall too! mostly i like that they look good with everything, even dresses, and are more comfy than heels!!

  38. a BIG yes from me. I love how they look on guys (swoon) and on girls as well. I bought myself sperrys in dark brown but had to return it bc I bought a size too small. but when I find my size, definitely getting again.

  39. I am absolutely jumping on this bandwagon!!! I love them.

  40. I love wearing my Sperry’s in the rainy Holland weather. The LLBeans on the top of your graphic are so cute!

  41. Do! I just bought my first pair (Sperrys) & I love them! German women where we live always wear them, so it’s nice to start fitting in with the locals. They’re also incredibly comfortable and double as rain shoes for all the summer storms we get. May have to get those L.L.Bean Signature ones for fall though…

  42. “Yes” if I am going on a boat! “No” if I am staying in the city!

  43. Don’t! Not for me, but I bet there are many women that cal pull it off.

  44. Personally I wouldn’t wear them, however here in Melbourne they leave the impression you live in a certain suburb and promote the fact you own a boat! So that said I’m sure they would look very ‘tres chic’ in NY and of what I know of your style though your blog, you’ll pull this look off with aplomb!

  45. Please for Christ sake help this poor boy from Haiti