From Day to Drinks (+ a major giveaway!)

June 1, 2015

wit & whimsy I meghan donovan I styling sneakers

So back when I was about to start my very first internship in advertising/marketing, I was talking to my Dad about the commute. I was home in Chicago for the summer (I went to school out in California) and had secured an unpaid internship down in the city. The commute involved a drive to my town’s train station, a 30 minute train ride and then walking 15 some odd blocks from Chicago’s Union Station to my internship’s offices. My dad immediately commented “well you’ll need a new pair of sneakers to do that walk in every day.” I remember my over-dramatic reaction with my mouth dropping and my declaring “I will never be one of those women who commutes in sneakers with their dress clothes on.” Oh what little I knew…

wit & whimsy I sneakers and a dress

As a proof point I did walk in J.Crew flip flops every day to my gig but now I laugh at the story. 19 year old bodies are so much more nimble than nearly-30 year old bodies and comfort quickly reigns supreme the older we get, right? Anyhow, this outfit brings such a smile to my face because I was that girl…commuting in a dress and a pair of sneakers.

wit & whimsy I how to style sneakers

Thankfully sneakers have gotten a much needed makeover by most brands these days and I picked up these colorful kicks at a recent DSW stopover with my roommate Alyson. Their colors make them perfect for pairing with Spring dresses and skirts and when it comes to get drinks later in the day, I slip on a pair of heels. I also have to make a more concerted effort to stop relying on athletic wear while running errands on the weekends. Pairing sneakers with your outfit and then stashing a pair of heels in your bag makes it easy to transition from running around the city to heading straight to happy hour with friends.

wit & whimsy I banana republic dress

wit & whimsy I meghan donovan blog

These Alice + Olivia pumps are the perfect neutral shoe. They’ll go with anything and since I already owned a pair in another pattern, I knew they’d be a great buy.

wit & whimsy I day to drinks

Onto more of what you’ll be excited about in today’s post 🙂

wit & whimsy I charles and colvard giveaway

Always wanted a pair of the perfect studs? Now is your chance. I’ve teamed up with Charles & Colvard to giveaway a pair of their Forever Brilliant Moissanite Bravo Earrings – retail value $299! Seen styled in this post, Moissanite is the strongest alternative to buying a diamond has more brilliance + luster than a diamond and is ethically sourced and conflict free. Better yet? Only Charles & Colvard Moissanite is made in the USA and comes with a limited lifetime guarantee. You can find out more about moissanite and its benefits at I’ve been wearing mine practically non-stop. They are the perfect size!

Please note in order to be eligible to win you must like Moissy’s Facebook Page, wit & whimsy’s Facebook page and leave a comment on this blog post! Details below to enter via Rafflecopter.

wit & whimsy I spring neutrals

wit & whimsy I meghan donovan I little white dress

Shop the Post:

Banana Republic Dress

Suede Pumps (also have them in snake print -so comfortable!)

Nike Sneakers

Denim Jacket (more denim jacket picks)

Kendra Scott Two-Finger Ring (c/o – I get so many compliments on this!)

Gorjana Wrap Bracelet

La Mer Collections Watch

Leopard Clutch

Charles & Colvard Earrings (c/o)

BaubleBar Heart Pendant (c/o)

Monogrammed Necklace

Celine Sunglasses

a Rafflecopter giveaway
wit & whimsy I sneakers and dress

And more colorful kicks:

[Bekka Palmer Photography]

comments +

  1. Samantha S. says:

    Hi Meghan!
    I think it’s so funny that you mentioned the conversation you had with your dad about investing in sneakers for your commute, because my sister and I just had that conversation last night and just about every night the last week! My sister and I, both being in our early 20s, often struggle with the idea of toting a spare pair of shoes in our handbags or just changing when we get to where we need to be, which is why I’m so inspired by the way you styled this outfit. I’ve read about pairing sneakers with dresses in fashion magazines lately, but never really thought it worked. Your post gives me a new perspective though and your smile in these pictures definitely gives me a little bit more confidence to want to try this look. If all else fails, maybe a nice pair of earrings will distract people from looking at my shoes! 😉

    • Meghan says:

      I love it! So you know exactly what I was referring to haha. My dad and I still joke about this but my how the tides have turned in what I deem acceptable 🙂 I think you should definitely try the styling out (and report back!)

  2. Jess Zimlich says:

    I can’t really think of a reason that I wouldn’t want to win them 😉 But in all reality, I’ve actually been reading a ton about moissanite stones recently in terms of rings and I like what I see so far!

  3. KT says:

    These look great on you! I learned about Moissanite recently and am definitely interested in owning some. I’d wear these for my wedding!

  4. lindsay says:

    love those sneaks! would love to win the studs because i recently lost a pair of go-to earrings. these would do nicely!

  5. Hannah says:

    I’m just starting to come around to the sneaker-and-dress combo, but I love the pairing here. I think the denim jacket really ties the look together perfectly. Thanks for sharing!

  6. Buck says:

    You know how I love sneaks 🙂
    And diamonds 🙂 🙂

  7. BStarkles says:

    I THOUGHT I noticed some extra BLING in your ears last week. A girl’s BFF, right? xo

  8. Kim Pincombe Cole says:

    Love these! I’m always tend to wear classic style stud earrings – simply because they go with everything & I forget to change them. I recently lost 1 of my diamond stud earrings (bday gift from my husband a few years back) at the hair salon – I’ve been so heartbroken over it!!!

  9. You’re so right about comfy shoes being a MUST! I wore heels all the time until I moved to New York and now flats are my BFFs.
    My current go-to studs are from H&M so those would be quite an upgrade! 😉

  10. Lizzie Lambert says:

    I would love to win these so that I have the perfect pair of earrings as I start my new career. As a student, I have had a difficult time adjusting to professional work place attire, but these earrings would be a great transition piece for any thing or any place I have to go! Love the blog and get new outfit ideas from you all of the time! Thank you!

  11. Elisabeth says:

    Wow! Such beautiful earrings. I love timeless, classic earrings so winning these would be wonderful! xoxo

  12. Brittnie says:

    Thank you for this amazing giveaway! Fingers crossed!!

  13. Megan Davis says:

    Comfort is key! Gone are the days/nights where I can walk around in heels and not feel it the next morning. What a great giveaway!

  14. Linda says:

    I love that the earrings are so simple and classy. It could dress up any outift!

  15. Megan says:

    Hey! Love your site and visit it often. Glad to see things are going great for you! These earrings are an awesome wardrobe staple and I feel like I need some like them in my life 🙂 xoxo

  16. denise says:

    These are such cute earrings. I would love to wear these on a daily basis- so pretty!

  17. Suzanne says:

    I would love to win because I currently do not own a pair of studs. These are so gorgeous.

  18. Darina says:

    Love these earrings! So versatile and gorgeous, perfect for every day and night. Love, love love!

  19. Marta says:

    These earrings are total classics! I’d love to win!

    PS – Love this dress! Two great outfits.

  20. Chelsea says:

    When my entire jewelry box got stolen out of a friends car while moving I lost so many of my favorite pieces, and I had a pair similar to these! I’d love to finally replace them with a gorgeous pair!

  21. dianne says:

    I would like these to give to my sister for her wedding present!

  22. kenny says:

    Pretty! Would love to wear these on my anniversary coming up.

  23. Taylor says:

    Love the dress and sneakers look! Dresses are a favorite of mine and I love being able to be comfortable and stylish at the same time!

    I’ve never heard of moissanite before but those babies are gorgeous! They’d be a perfect addition to my everyday earrings rotation. 🙂

  24. Jennifer says:

    I would love to win because I have lost all of my good earrings! These are perfect!

  25. Jessica Gipson says:

    I would LOVE to win these gorgeous studs because you can wear them with an fit and look like a diva.

  26. stacey grantham says:

    I am all about looking good, but being comfortable at the same time. I do not want to suffer for fashion, so sneakers are a necessity. I love the stud earrings as they can really dress up the simplest outfit!

  27. Karrie Millheim says:

    They are so pretty.. I would pair them up with a cowgirl outfit. skinny jeans. my boots and a jean top!! i think they would look amazing

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