I resisted adding the Chelsea boot to my wardrobe for years. I suppose that I felt like the style was too chic and modern for my more classic and feminine style, but I was starting to come around to the idea and stumbled upon the perfect pair by complete accident.
I will start off by saying that flats are definitely more my vibe lately because they’re just easier to put on and to chase Sophie around in (please see my Freda Salvador sneaker review and any of my posts about Rothy’s 😅). Being a mom doesn’t necessarily mean giving up heeled shoes altogether, but nowadays I definitely find myself reaching for flat styles more often for everyday activities. It’s nice having a [mostly] flat sole boot option in my closet that isn’t my pair of tall Hunter rain boots (which I still love, but they can be too clunky for some activities).
I love that these shoes are constructed of waterproof rubber (as they are technically rain boots), have a lighter brown piping trim so that they’re not fully black, come up just high enough on the ankle (not too low or too high), have just a bit of heel but are mostly flat, the sole isn’t too chunky, and obviously I adore the bow detailing on the back of the shoe to add a pinch of femininity.
I will say that because they don’t have a clunky lug sole the tread is probably lacking in the traction department so I don’t think they’ll be ideal for super wintery weather; just something to consider!
As far as sizing goes, I went up a half size from my normal because I wanted to be sure that there would be room to fit a thicker sock, but I don’t know that I necessarily needed to as the shoes feel plenty roomy on their own and are easy to slide in and out of.
I think that another resistance that I was having to the Chelsea boot was that I didn’t know how to style them so that they would work with my existing wardrobe. I certainly didn’t want to have to buy outfits JUST to wear with the shoes! Thankfully, some fellow bloggers that I love to follow are more knowledgeable about fashion (namely @jesskeys_, @karlareed, and @merricksart) and they styled their Chelsea boots in enough ways that I could start to envision how they could make their way into my wardrobe.
I personally plan to wear them mostly with pants (skinny and straight leg styles alike), but I’ve seen people pull them off with skirts and dresses too! I like the bare ankle look as well as having a chunky sock scrunched around the ankle for both styling and warmth purposes.
Below are a few of the ways that I plan to wear my new boots and I can’t wait to style them! (haha — is it obvious that I have a thing for neutrals??)
All of this to say: you don’t have to jump on a trend right away (not that Chelsea boots are necessarily a trend because they’re a pretty classic boot type, but they’ve been trend-ing for the past few years).
(1) observing how others with a similar aesthetic are styling the piece that you’re considering — utilize Pinterest or do a hashtag search on Instagram or TikTok including the item name,
(2) taking the item for a “test drive” by trying it on in a store and see how you feel about it while you’re actually wearing it (bonus points for saving money / landfill waste by buying these items secondhand on Poshmark or Mercari to try out a new-to-you style!), and
(3) don’t buy a style of something right away if it doesn’t speak to you and your aesthetic! I saw this pair and immediately knew that they needed a place in my closet, but haven’t felt that way about any of the other styles I’ve seen over the past few years. If you wait long enough, the right design will find its way to you!
If bows aren’t your vibe, but you’re still looking for something classic, these are the options I was considering before I discovered the Bernardo Briton style:
If you’ve been on the fence like me and have a similar style aesthetic, I can’t recommend these booties enough! I’m crazy about them and think they’re going to be such a great addition to my closet.
Happy shopping, friends!
Sending hugs —