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Q&A: What to Wear on a Tall Ship

July 20, 2009

L-A: With all of our time spent prepping for the live show this weekend, my Sudafed-head, and the need to soak up some sunshine while we’ve got it (no idea how long it’ll last), we haven’t got much of a plan for a Monday morning post. So, I’m going to suggest we re-visit a question that we tackled during the live show.  Jane, one of our readers, posed the following question:

Q: I have a great navy and white striped shirt from H&M with a boat neck, but have a hard time figuring what to pair it with. When I wear it with khakis, I feel like Im channeling Gene Kelly in Anchors Aweigh – you know, when he’s dancing with the little cartoon mouse?


A: When looking at this photo on Saturday, Ally and I came to the conclusion that we actually liked Gene Kelly’s outfit. Not as an everyday sort of thing, but if you lose the hat (and the cartoon mouse) and change the shoes, you might have something there. We’re fans of the high waisted sailor style pants. Granted, I can’t wear that style, but if you can, go for it. As for shoes, we are overwhelmingly in favour of the wedge.

But, that answer isn’t quite enough, is it?  So, we had some fun with Polyvore and came up with a few outfits that work with such a striped shirt. Granted, the striped shirts in these sets aren’t exactly what Jane described in her question, but I think you could interchange any of them quite nicely.

What to Wear on a Tall Ship 1
What to Wear on a Tall Ship 1 by Ell_Eh
Cute shorts, cute tote, a pair of sandals, and aweigh you go!  Next up:
What to Wear on a Tall Ship 2
What to Wear on a Tall Ship 2 by Ell_Eh
Those cute Current/Elliott boyfriend jeans that celebrities are all aflutter for and I can’t afford, a cardigan in case it gets chilly, and some cute shoes. As for the brand of your boyfriend jeans, it really doesn’t matter if they’re those particular Current/Elliott denim. As cute as they are, I’m sure some of you ingenious readers can find a more affordable incarnation of the boyfriend jean.
What to Wear on a Tall Ship 3
What to Wear on a Tall Ship 3 by Ell_Eh
These shorts are a cute way to do the high waisted sailor pants without going completely Gene Kelly. Again we’re all over the wedge sandal. I know this is the summer of the gladiator sandal, but in case you haven’t noticed, I’m ignoring this particular trend. There are few circumstances where I can honestly say I’ve liked a pair of gladiators (although, our model Tara did rock a pair today with leggings and a cute dress/top from Sweet Pea. There will be pictures soon).
What to Wear on a Tall Ship 4
What to Wear on a Tall Ship 4 by Ell_Eh
I love these shorts. Cannot wear them (shorts of any kind do not do not mix well with my thighs), but they are adorable. This pair that I found on Polyvore are from Arden B., but I have seen a similar pair at a Joe Fresh store.  Also, is it just me or are these enamel Kate Spade bangles not the most adorable? They also sell for under $100 (! almost affordable! if I wasn’t a student, they would actually be affordable) at and make me very excited to visit the Kate Spade outlet near my parent’s place.
Also, we are aware that the wedge sandal, or any kind of heel are not exactly appropriate sailing attire. But Jane didn’t ask us about what to wear sailing and neither Ally nor myself sail. In fact, I’ve never been on a sail boat in my life. But I do like to look as though I might be headed off on a very glamourous sailing adventure. The above outfit is very Mary Ann and very cute, but don’t wear pigtails or you might end up looking like you’re in costume.
What to Wear on a Tall Ship 5
What to Wear on a Tall Ship 5 by Ell_Eh
I’m in love with this Burberry top and am now on a hunt to find something similar that costs less than $250.  The J.Crew pants are an example of how to do a wide leg with the striped top. With the wedge or a flat sandal, you can avoid looking like Gene Kelly.  Also, am loving the anchor on the purse.  Our model/guest blogger Jo had something similar at the show in a grey and black by Montreal company Jak’s that is available at Lady Luck Boutique (home of some of Halifax’s cutest accessories).
Over to you Ally. I’ve once again done a poor job setting up the post for you. I’m going to blame today’s Sudafed-head for that.
AllyG: This is a fantabulous post. Loves it. Particulary because you wrote it while I put up my swollen feet for the majority of yesterday afternoon/evening. Honestly. No word of a lie. I spent a 1/2 in kitten heels during our webcast yesterday and I am paying for it dearly.
We had a fantastic show yesterday. Many thanks to our retail sponsors and models. More on that tomorrow (hopefully), we’re hoping to have our photos back today (we had to develop them all old school like).
We’ll also hopefully have a link to the webcast for you this week. Sit tight for that. In the meantime, I’d like to add an accessory to Jane’s outfit. The fedora. This blog writes a love note to my favourite hat of all time. And why not with a striped shirt?
Cameron kills the fedora look. In fact, she does it better than her ex JT. Did you see Cameron in last month’s Vogue (was it last month?)…

If I was Jessica Biel I would want to eat my own arm in jealousy.
Sorry. Fedora. Where was I?
Fedora + striped shirt = Tall Ships Hotness.
Happy Monday everyone. Can’t wait to show you our fashion show post.
Ally xoxo
10 Comments leave one →
  1. Eden permalink
    July 20, 2009 2:10 pm

    1. I now need some high-waisted sailor pants.

    2. or the sailor shorts!


  2. Jane permalink
    July 21, 2009 11:31 am

    Thank you! Amazing!

  3. Jen permalink
    July 21, 2009 11:53 am

    I love your blog! Loved the Bachlorette feature…I too noted what a great dresser that Jillian is. This was another great one. Keep it up!

  4. J. Rousseau permalink
    December 21, 2011 1:32 pm

    Well, as a tall ship sailor my self, these ”fashions” would be more what ou would wear as a tourist, not for working. What you wear more when you sail on a Tall Ship would be Boat Shoes, Jean shorts or Kapris or Kakhis, and a Tee Shirt or a Ribbed Undershirt or a plaid shirt if it’s cold, and , for a hat, either a Fedora or a Sun Hat and Aviator or Dollarama sunglasses. :-), as you can see, sailors are very simple people who don’t necessairily wear the top styles.

    • la permalink*
      December 21, 2011 10:33 pm

      We had a feeling these were high impractical choices for actually wearing on a tall ship. My own seafaring experience has been limited to a commuter ferry, a booze cruise and large passenger ferries going from NS to Nfld…so not at all qualified to recommend what one would actually wear on a tall ship.

      • Julieanne permalink
        December 26, 2011 6:15 pm

        yeah, you just have to watch out, and if you are going to go a any actual sailing vessel, what i recomended before is perfect to wear. :)

  5. J. Rousseau permalink
    December 21, 2011 1:34 pm

    oh and NEVER EVER wear high heels, it is VERY DANGEROUS, and some ships won’t let you aboard if you are wearing high heels.

  6. J. Rousseau permalink
    December 21, 2011 1:57 pm

    sorry, I keep forgetting things, but don’t wear jewlery either, it attracts sailors and crew of the ships to stare uncontrolaly @ you, and it’s very creepy for the person wearing the jewlery. :-) as you can see, we’re (sailors and crew) very weird and….different.
    ”Cookie” (trust the cook to tell you good information)


  1. Favourite Friday: July 20 Edition | Fashionable People, Questionable Things.

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