This has been my uniform as of late. A button down shirt, comfy skinny jeans, navy school boy blazer, and my “grandpa shoes”. A sweater (or sweater vest in this case) gets added if the temps dip into the chilly range, which it has recently.

A lot of factors about ourselves can make us reach for particular types of clothing over others. Depending on what you deem flattering on your body type, or the type of activities you participate in, some clothing is just better suited for us or easier to wear. I’m learning that I avoid pull-over type clothing, opting instead for items that button or drape, the reason being my hair. Having naturally curly, fine, and frizz-prone hair, I prefer to avoid pulling fuzzy knits over it, which just messes up the peace-treaty I’ve made with my hair that day. My daily wardrobe is reflecting this…button-down shirt, and blazer…no hair-frizzies involved. When I do pull a sweater over my head, it’s usually followed by some intense damage control.


I love the color and shine of these penny loafers. Called “Cordovan”, it’s a perfect mix of deep red and brown hues which I’ve found to be pretty neutral. The shine makes them a little dressier, which adds a little oomph to a basic outfit.

Cole Haan has been a favorite brand of mine for quite some time, so I was sad to hear the company was recently sold by Nike, which means they’ll most likely be losing the Nike Air technology that has been credited in making Cole Haan shoes so comfy. I may need to round out my penny loafer collection with a nice black pair from them in case Nike Air really does disappear from the brand.


Outfit detailsJ.Crew Crewcuts blazer :: Theory sweater vest (in grey/navy) :: Banana Republic shirt :: Rag & Bone jeans :: Cole Haan loafers :: Valentino handbag (in beige & light green) :: Kate Spade watch :: vintage brooch :: Saks Fifth Avenue pocket square :: pearl bracelets :: Daisy Knights ring

Altered – Banana Republic shirt has had seams added :: Kate Spade watch has had the strap changed :: pearl bracelets have been shortened

Join the Conversation


  1. says: Jenny

    I went to Cole Haan today to look at their Chelsea pumps and asked the SA what’s going to happen to the Nike Air technology in the shoes. He said that Cole Haan is keeping the technology, but it might be renamed to remove the Nike name. I hope that’s helpful :)

  2. says: Franziska

    I, for one, love the “grandpa shoes”. I have a pair of lighter tan ones, but I like the patent version too. Also, thank you for the idea of using a sweater vest. I like the look of the sweater over button down under blazer, but the added sweater would add too much bulk to my shoulders.

  3. says: Madalina Tita

    the bag is amazing! so edgy and fashion forward, it really brings the outfit to another level!



    1. Eventually I’ll get this blazer taken in at the back like I did with the herringbone Crewcuts one, but I haven’t yet. It’s a size smaller, so it’s not as boxy, and is wearable in a relaxed-look kind of way. I’m wearing it so often that I don’t want to hand it over the tailor for a week! I’ll probably tailor it when the weather warms up and I’m not wearing a blazer pretty much every day.

  4. says: Ammera Kaing

    You look great Kelly! I’m bummed to hear about Cole Haan being sold too. They’re one for my fav brands for well-made, comfortable shoes.

  5. says: Jen

    I have a pair of Cole Haan brown suede penny loafers too! They’ve stuck with me for the last few years when I want to get my grandpa-chic on. ;)

  6. says: Carolyn Otto

    The Theory sweater vest was on “Happy Endings” tonight! She styled it with a white button down and grey skinny jeans. Cute! I always love when a professional wardrobe stylist dresses a character in something I own!

  7. says: Jen

    I tend to uniform it up on the weekend, too. It’s often jeans and blazer or jeans and a sweater, but, I’m missing the bootcut jeans, I have to say. My skinnies are fine, but I have a fuller backside and as a petite who is otherwise small, I find the skinnies just aren’t that flattering on my shape, and the bootcuts balance me more… Unfortunately my fave pair of those ripped about a year ago, and my fave manufacturers seem to all favor the skinny cuts….sigh. Kelly do you have any suggestions?!

    1. Have you tried the Paige Laurel Canyon? There is a slightly darker wash that I always see that runs really small. I have to get a lot loped off the bottom, but I find it leaves a much smaller and more flattering size bootcut. I see them all the time at Nordstrom Rack (if you’re US based) for a good price.

  8. says: liz

    love love love your style. We have the same body type too ! As far as flats go, I’m stuck. I am sick of tennis shoes but when I try flats, my pants just look wrong and I feel really short. I am thinking that my pants are hemmed to long when I get them altered. What flat shoes do you wear with straight leg jeans, and where IS the hem supposed to be on jeans?

    1. Hi Liz! I prefer flats with a low cut toe box. When a flat shoe shows a lot of “skin”, it just looks so much better with straight or skinny pants, and makes your legs look longer. As far as hemming goes, it depends. Straight leg jeans are a little tough and I’ve largely given up on them and gone straight to skinny jeans. I think straight leg jeans look best without much scrunching or breaking in the leg line, so hemming them so they just rest on top of your shoe (tad below ankle for flats, maybe 1/4th of the way down the foot for heels) is a start. But, like I said, I never really mastered them myself, so maybe try a jean that’s more tapered at the ankle if you’re still struggling. Good luck!

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