Johannah writes: "I am a regular reader but have never turned to you for help until now. I recently decided to start going through everything in my closet to see if I can actually wear everything or if I can get rid of anything. I came across a pair of floral Doc Marten boots (see attached) I bought at the end of high school or beginning of college that I wore a few times but never really knew how to handle. I am hoping that you can either A) tell me to ditch them because they are horrible or B) help me style them now in my late 20s. I would say I tend towards girly styles like Zooey Deschanel but I would not limit myself to that. I have 2 older brothers and like to mix some tomboyish items with my girlier items. I love being comfortable and running around with my husband, friends and dogs. While I am a young professional I still have a limited budget so if I could make an outfit around the boots for about $100 that would be amazing but I would be willing to consider some splurge items if they are good quality. I love gem tones, black and gray. I also think that it's worth noting that I have short curly hair."
Johannah, it's Mitchy, and this request really spoke to me. On top of relating to pretty much everything in your description of yourself, I too had some red Doc Martens in high school that I was not quite cool enough for yet. Unfortunately, they're no longer with me, but I can live vicariously through your request.
I'm sure some of our readers would claim these shoes are horrible, but if there's ever going to be a time to rock these it's right now. Combat boots are in, and so is the oxblood color, so it shouldn't be too hard to find stuff to match. Your Personal Shopper comes with two disclaimers though: one, please ditch the ribbon laces for thin black ones, and two, you'll probably want to hold off on putting these outfits into rotation until fall or winter - they're a little moody for summer.
That said, I think these boots would be great with an LBD, but it'd be boring to show you a bunch of those. Instead, try a burgundy A-line dress like the 1. Feeding the Doves Dress in Berry ($70) with a 2. basic cardigan ($29). Red and black can get gothy pretty quick, so keep the jewelry lightweight with something like these 3. textured bangles from Target ($15). I thought about a bag in a contrasting color, but those boots have a lot of look already, so I'd actually keep the purse simple with something like this 4. R&J Skyler Clutch ($48).
For a more casual, tomboy look that's still professional, try this 5. Tiered Ruffle Cotton Cami ($40). An 6. oversized grey cardigan ($35) and an 7. ivory crossbody ($49) will contrast well with a 8. pair of skinny black jeans ($80, but you might/should have these in your closet anyway).
Your particular pair of Doc Martens are hard to duplicate, but if readers are looking to recreate these outfits, I've included a pair of cherry red boots ($140).
I hope I've helped you breathe some life back into your boots, but if you're still not so confident about them, I'd suggest putting them on Etsy.
Frustrated in your search for that perfect leather handbag, red stiletto pump, or whatever makes your heart go thump in the night? Click here to check out our requests for you, the reader, and to contact us, and we might do the shopping work for you in a future Personal Shopper feature!
Mitchy here: I'd be happy to never put on another pair of pants. What this means for you is that I love all kinds of dress shopping - especially cute patterned dresses and party dresses. I also love colorful apparel and jewelry as well as vintage-styled home decor. Other things I don't usually put on resumes: expert cat wrangler, road tripper, and connoisseur of bad movies.
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