I’ve been hesitant to try flat ankle boots for fear that my size 11 feet would look like massive, manly leather-covered blobs. When Long Tall Sally kindly let me pick a couple of fall items to try, the classic brown Chelsea boot caught my eye and I decided it was high time I conquered my fear of ankle boots. When I opened the shoe box, I gave the somewhat large looking boots a dubious glance. Slowly and suspiciously, I took them out and put them on, felt how comfortable they were, admired how classy they looked and realized that my preconceived notion about ankle boots being unflattering on my large-ish feet was entirely incorrect.
Then the real fun began as I started to play dress-up and realized that these boots have the potential to see a lot of wear this fall! Without further ado, I present you with my 4 ways to wear Chelsea ankle boots.
Look #1 – Black Skinny Jeans+Striped Shirt+Floral Scarf+Field Jacket
Last weekend, we took a quick trip to Paris and I wore this outfit one of the days (secretly hoping to score some amazeballs photo ops around Paris for the blog). Unfortunately, I didn’t get a chance to take any blog photos in Paris but I CAN tell you that these booties were quite comfortable for a leisurely Sunday walk through the City of Light. The only discomfort I experienced was the top of the boot rubbing against my leg a bit, but I think that’s because I didn’t have the right socks on. This outfit will definltely be one of my main go-tos for fall!
Look #2 – Chelsea Ankle Boots+Black Sweater Dress+Plaid Scarf+Tights
I’ve hit the 3C trifecta of cozy, classy and comfy with this outfit. A plaid scarf, tights and the boots seemed like the perfect items to pair with this basic black sweater dress for an effortless fall look.
Tall Sweater Dress – Ann Taylor (Old); Also shown here
Plaid Scarf – Jessica Simpson Collection (Old)
Tall Tights – HUE
Look #3 – Bootcut Jeans+Plaid Shirt+Animal Print Belt
Wearing ankle boots with skinny jeans is actually a bit trickier than I anticipated! Audrey from Putting Me Together recently did a very helpful write-up on the topic so be sure to check it out if you’re flummoxed about how to pair your skinny jeans with booties like I was. If I don’t want to bother with getting just the right “roll” or cuff on my skinny jeans, I figure I can just take the easy way out and wear the Chelsea boots with my bootcut jeans. I’ve often wanted to wear my J.Crew extended calf boots under my bootcut jeans but they are too bulky in the calf and make me look like I have lumpy legs. Now that I have ankle boots, that problem is solved. These jeans are so long that you can’t really tell that I’m wearing ankle boots even when I sit down. Huzzah! Hopefully I don’t look too lumberjacky with my plaid shirt, boots and jeans.
Plaid Shirt: Banana Republic (Old)
Belt – Loft
Look #4 – Button-Up Maxi+Denim Jacket+Tights
OK. This look is a bit “creative” for me (translation: out of my comfort zone). One of the style tips on LTS website for this maxi dress was to wear it as a long-line vest so I figured I’d unbutton all but 3 of the buttons and give it a try. I’m not sure if I’m completely sold on the look or if I can even pull it off but that’s the fun of playing dress-up, right? If I did wear this outfit, I might button the dress down a bit more. What do you think of this look? Yay or nay? Any suggestions on how you would make it better/different?
So there you have it! My 4 ways to wear Chelsea ankle boots from Long Tall Sally (which go up to a size US15 by the way). And now for a quick history lesson: Did you know that the Chelsea boot style is over 150 years old? The boots even have their own Wikipedia page that describes the interesting history! While these boots may be “trendier” some years than others, it seems to me that this classic style will always be en vogue and I’m happy to have them in my closet.
Which outfit is your favorite? Have you been hesitant to try ankle boots or do you already have a pair that you love?