In Which I Look Like An Insurance Agent

How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) []

Is this too weird? I feel like it might be too weird.

This is the series of events that lead me to traipse gleefully around Soho at 10 in the morning looking like an investment banker:

  1. The sartorial Aeneid that is Annie Hall celebrated its 40th anniversary last week.
  2. InStyle paid homage to the milestone with an editorial featuring Alexa Chung and some lobsters, impeccably decked out in the most gorgeous Annie Hall-inspired outfits (Alexa, not the lobsters).
  3. I thought “hey! I know how to tie a tie thanks to years of private school and a brief stint as a caterer!”
  4. I visited my grandparents’ house for Easter, where I acquired the requisite tie and also five pounds.
  5. I didn’t feel like shaving my legs. 

Which brings us to today. Admittedly, the final product is decidedly less “menswear-inspired” and more “legitimate man” (in heels) (it’s 2017!).

How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) []

But then again, this isn’t surprising when you consider the fact that I am a person of extremes. Oh, you’re wearing a button down and boyfriend jeans? Cute! I see your “menswear” look and raise you a full suit that’s two cufflinks short of an insurance agent.

Am I pulling it off? Jury’s still out. In the process of shooting this, I was thanked by an elderly gentleman (my target audience) with no follow-up explanation. I was also given the once-over by a group of Lululemon-clad 20-something year olds en route to Ballet Beautiful who, judging by the less-than-discreet disparaging expressions they catapulted in my general direction, were less than enthused by my getup.

How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) []How To Wear A Suit 101 (sort of) []

One part of my outfit that’s significantly less controversial is the gorgeous watch by Victoria Emerson. When I visualize people who really have their shit together, in the form of a 5 year plan and steady rotation of vegetables in their diets, they’re all wearing some variation of this watch. Simple, chic, and timeless, it’s a piece that goes with everything and has already become a staple in my wardrobe.

It even has rose gold detailing. I fux with some rose gold detailing.

How To Wear A Suit 101 (sort of) []

You can purchase the watch online now; it’s on sale, but just in case you needed an extra lil nudge, use this coupon code to get an extra 30% off your order.

How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) []

I thought it the perfect accessory for this “suit” (which of course is not a real suit, because I’m not Olivia Pope) to pull everything together. A sensible watch demands a sensible outfit, no? It would be near blasphemy to pair it with leggings. Not that I would do that, because leggings as pants registers at #4 on my personal 7 Deadly Sins ranking, but you get the picture.

Though maybe next time, I’ll lay off the tie.

Thank you to Victoria Emerson for sending me the watch to feature! As always, all opinions are my own.

How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) [] How To Wear A Suit 101 (sort of) []



  1. I never feel like shaving my legs lol. Your posts always make me laugh! You have such a talent for writing and fashion!

  2. You pull this off perfectly, girl! The dark lip completes the look!

  3. Your writing always makes me smile. I think you can rock anything if you have the confidence! You look so great girl!

  4. You look really good in a suit! I feel like I wouldn’t be able to rock a suit as well as you did! I am really lovin’ the dark red lipstick you paired it with too! 🙂

    xo, Chloe //

  5. You rock this look which not a lot of people can do!

  6. Your post titles always kill me because I click on them and there you are, SLAYING in whatever your outfit is!

  7. jennyblaisdell

    Your fashion sense is killer and your writing is funny and relatable. Just overall killing it.

  8. Ditto #5! Pants are my go-to whether it’s winter or not when I don’t feel like shaving my legs. You look great though! And this post was hilarious. 🙂

  9. you are pulling it off!! Although you totally remind me of Madonna in this look!

  10. Loving those block heels with the cropped pants.

  11. Your shoes definitely lower the insurance agent look 😉 you look more like a spy actually… Jane Bond? 😉

  12. The heels definitely lessen the insurance agent feel haha. And honestly, if the jacket was more tailored to a woman’s body, you’d look like a million bucks! Love the menswear inspo though – you’re definitely rocking it!

  13. Though you’re not Olivia Pope, I still think you pulled it off!


  14. OMG I love this. You seriously look like a runway look brought to life.

    The Classic Brunette

  15. You look EPIC – like you should be in a James Bond movie!

    Coming Up Roses

  16. You look absolutely stunning. Love all the shots.


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