Set Sail with Helly Hansen

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Fewer things say Summer to me than a casual afternoon on the lake.

This past Sunday marked the last day of racing for the Chicago Helly Hansen National Offshore One Design (NOOD) Regatta, the largest national sailboat racing circuit in the United States. More than 150 sailboats and hundreds of local and national sailors came together over four days on Lake Michigan for competition in one design races, where similar types of boats race against others in their own classes. Shawn and I had a front row seat for all the action as we spent Saturday morning with one of our favorite brands, Helly Hansen.

Helly Hansen, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club, Helly Hansen Sneakers,

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Chicago, Lake Michigan, Helly Hansen NOOD Regatta, Sailing in Chicago, Chicago Yacht Club, NOOD Regatta Chicago

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Jacket, Sailing in Chicago, Lake Michigan, Chicago Fashion Blogger, NOOD Regatta Chicago, Helly Hansen Sport Dress, Nautical Style, Chicago Yacht Club

Helly Hansen Welsey Trench Coat c/o || Helly Hansen Thalia Blouson Sport Dress c/o || Helly Hansen Sneakers c/o

The weekend was absolutely gorgeous.  After a few hours delay Saturday, the wind came in strong enough to sail two good races. Skipper Bradley Faber of Owassa, Michigan, and crew of Utah won the opening race. Though the challenging conditions produced close racing, Chicago local William Smith and crew aboard the Wooton (who placed third in the first race) emerged as the leaders after day one.

Sunday, we were also so excited to see the first-ever Helly Hansen Junior Crew, comprised of four local teenagers, competed against the pros in the J/70 class. They finished 19 overall.

The overall winner, chosen based on the strongest finish in the most competitive class, will receive an invitation to compete against the winners from the other four series stops at this year’s Helly Hansen NOOD Regatta Championship, hosted by Sunsail, in the British Virgin Islands Oct. 22-28. The winner of the North American Championship will also be announced at the culmination of the event on Sunday, June 19. Sign me up for a front row seat at that competition, please!

With the weather as perfect as can be, being on the lake was exactly what Shawn and I needed to get us back to zero. If you had an opportunity to read the ‘rainy day style’ post we did a few weeks back, you know we are big fans of all things Helly Hansen.

To launch sailing season in Chicago, we invested in our nautical style with this light weight striped dress and sneakers.  Let me tell you, this dress is the most comfortable one I now own. It was so lightweight – almost feeling like silk. When the cool winds picked up a bit in the morning, this trench jacket was just the ticket to fight the temperatures, but equally breathable enough when the day heated up.  Their gear is a true go-to for all seasons.

Also, join us on Snapchat to see more fun from this weekends NOOD Chicago Regatta! @alilyloveaffair

________ Sales & Such ________

  • Guys! I am beyond excited this weekend is the Chicago Food Truck Festival taking place Saturday & Sunday – Shawn and I are so stoked!  If you’re in the ares, be sure to snag your tickets as well.  You can purchase there here!
  • And, don’t miss your chance to win a $1000 shopping spree to Fab.com! If you’re not already familiar, I promise you’ll fall in love!
  • Enjoy 30% off all sale items with code SUNSHINE at Kate Spade!
  • 5 stunning looks to prepare you for the upcoming July 4th holiday
  • Save an extra 40% sale prices at Banana Republic
  • Summer is officially here!  We’re raising a glass with the Ultimate Bloody Mary recipe.  Cheers!
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77 Comments

  1. June 22, 2016 / 8:40 am

    Love this trench coat, this looks super fun!

  2. June 22, 2016 / 11:26 am

    I love stripes! That trench is perfect too. Nice photos!

  3. June 22, 2016 / 11:41 am

    What a fun event and your look is so perfect (or so I imagine) for spending time on a sailboat. All this talk about Lake Michigan and seeing these pictures really makes me miss it!!

    Shannon
    Clothes & Quotes

  4. June 22, 2016 / 12:24 pm

    You’re wearing the perfect boat dress! I just got a pair of nautical shoes in the mail and now I feel the need to go sailing, too!

  5. June 22, 2016 / 4:55 pm

    I love stripes, so you know I gotta have that outfit. I would also like to get outside when it cools down a little.

  6. June 22, 2016 / 8:34 pm

    Food truck festival?! Count me in! Absolutely want to visit Chicago ASAP, as it’s been on my list for quite some time! xx Adaleta Avdic

  7. Heidi
    June 22, 2016 / 9:38 pm

    This is so fun Anna! I’ve been following you on Snapchat and I’m so happy you started, I love every single one! Please teach me your ways!

    Heidi || Wishes & Reality

  8. June 23, 2016 / 3:56 pm

    This outfit is so darling! I love sailing and being in the water. This outfit is perfect for that! I love t shirt dresses and sneakers, so this is right up my alley.

  9. Biana
    June 23, 2016 / 4:34 pm

    You are ready to set sail!! Love the outfit here and makes me want to go on a boat ride! xo, Biana

  10. June 23, 2016 / 5:14 pm

    Too funny. My son just came back from sailing. I should invest in my sailing outfits. 🙂

  11. June 23, 2016 / 5:24 pm

    This looks beautiful! You look lovely. Stripes are always a go-to with sailing. Love it!
    xoxo,
    E

  12. June 24, 2016 / 8:11 am

    How cute is this look? I adore this outfit (AND THIS STELLAR shooting location!). Miss you so much — reunion with the girls again soon??

    Xoxo,

    Ashley || Sed Bona

  13. June 24, 2016 / 8:44 am

    I’m loving all the navy in this look! Too cute!

  14. June 24, 2016 / 8:44 am

    I love your jacket! And the stress is so cute and definitely looks comfy. It’s the perfect layering piece.

  15. June 24, 2016 / 9:21 am

    We went to the Annapolis boat show last year and I had a lot of fun dreaming about all of the things in Helly Hansen that I really wanted , but couldn’t justify buying. I love these boat looks. So summery!

  16. June 24, 2016 / 9:42 am

    Sailor chic!!! So cute and how fun to be out on the water for that! xx

  17. Jolina
    June 24, 2016 / 9:53 am

    Love the nautical style even if I don’t sail lol. It’s a classic look. Just lovely!

  18. June 24, 2016 / 10:09 am

    Wow that is such a cute jacket!

  19. Tamara
    June 24, 2016 / 10:35 am

    The coat is absolutely gorgeous and the stripped dress is perfect for a day sailing!

    XoXo,

    Tamara – LoveofMode.com

  20. June 24, 2016 / 1:58 pm

    That jacket is gorgeous! Love it!

  21. June 24, 2016 / 2:24 pm

    How fun! Sailboats actually really terrify me, but I always like to think I’m the kind of person that would go sailing haha!

  22. June 24, 2016 / 3:28 pm

    These are awesome pictures. I’m loving the outfit. The trench coat is amazing!

  23. June 24, 2016 / 3:46 pm

    You were very lucky to be able to board a boat and have a photo shooting on it. I would love to experience this at some point in my life. I live near a harbor with stunning boats but I don’t know anyone that owns one, haha. Your outfits are very lovely, I like the nautical theme.

  24. June 24, 2016 / 4:24 pm

    Literally love this post!

  25. June 24, 2016 / 6:50 pm

    Awesome pics, babe!

  26. June 24, 2016 / 8:05 pm

    I like the “Sherlock Jacket” haha, it’s so cool

  27. June 25, 2016 / 5:27 am

    You had such a cute outfit. I liked the dress although I would prefer that it`s a bit longer. I liked the nautical theme.

  28. June 25, 2016 / 8:35 am

    I love the coat and the sneakers most! Would love to get a pair of it!

  29. June 25, 2016 / 8:47 am

    This is such a cute post, you look adorable as always.

  30. June 25, 2016 / 9:00 am

    That dress is so gorgeous, I love stripes! Loving ya blog too.. let me know if you want to follow each other and keep in touch, i’m always looking for new blogger friends! x
    adelelydia.blogspot.com

  31. June 25, 2016 / 9:01 am

    GREAT look and perfect location!!! xo

  32. June 25, 2016 / 9:05 am

    Absolutely love our attire…..the dress, shoes and the trench coat. You carry it so well.

  33. June 25, 2016 / 9:28 am

    How fun to be able to take part in this event! And you’re dressed appropriately, and adorably! Love the outfit!

  34. June 25, 2016 / 11:11 am

    You had such fun and sunny weekend. Also your outfit rocks! Perfect for that occasion.

  35. June 25, 2016 / 11:22 am

    I love your striped dress and jacket looks perfect on it! Your pictures are beautiful. Looks like you had so much fun!

  36. Ashley
    June 25, 2016 / 12:25 pm

    You are the cutest!! This post is perfect from the outfit to the location! So obsessed with that dress!

    xo Ashley

  37. June 25, 2016 / 12:33 pm

    Great sense of fashion, the cost is my favorite. The color is perfect and ideal for spring and fall. Love it 🙂

  38. Angelle Marix
    June 25, 2016 / 12:57 pm

    You look beautiful!! And, every picture had me drooling. What a perfect day on the water. Love the striped dress and trench.

    Xoxo,
    Angelle
    http://www.dashingdarlin.com

  39. June 25, 2016 / 1:28 pm

    I love everything about this! Helly Hansen is one of the corporate sponsors for the resort I work for and they do our uniforms but I had NO IDEA they had a stylish line of cloths like the dress you’re wearing! SO SO SO CUTE!! Hope you had fun at the sailing races!

    http://www.darlingdailyblog.com

  40. June 25, 2016 / 11:53 pm

    Love the stripes and the coat – so fun!

    xoxo, Jenny

  41. June 26, 2016 / 3:51 pm

    Such a great outfit – love the simplicity and the edgy vibe. Cool phots

  42. June 27, 2016 / 2:42 am

    I love sailing, is one of the perks of living in an island haha. You seemed to have a great adventure. You are so chic!!!

  43. June 27, 2016 / 5:22 am

    It looks like you had a wonderful day! Love the look, Anna 🙂 Have a nice week!

  44. June 27, 2016 / 10:00 am

    Such a beautiful look and this look like so much fun! Your photos are gorgeous as always!

    Xo,

    Brittany || The Everyday B.

  45. June 27, 2016 / 10:10 am

    Perfectly nautical chic! Love these shots of you!

  46. June 29, 2016 / 9:29 am

    This is such a cute outfit!! And I’m definitely inspired to go out on the water this weekend after seeing that beautiful sailboat!

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