How to style ankle boots

4 Ways to Wear Chelsea Ankle Boots

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.

Size 11 Ankle Boots for Women

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!

Striped Top: Long Tall Sally
Jeans: Tall J.crew Reid Jeans
Jacket: Tall J.Crew Downtown Field Jacket
Scarf: Banana Republic (Old)

How to style ankle boots and skinny jeansLong Tall Sally Chelsea Ankle BootsSize 12 Chelsea boots for women Size 13 Ankle Boots for Women

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

Sweater dress ankle boots Chelsea boots with tights

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.

Jeans: Tallwater
Plaid Shirt: Banana Republic (Old)
Belt – Loft

Chelsea boots bootcut jeans Ankle boots bootcut jeans

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?

Button-up Maxi: Long Tall Sally
Denim Jacket: Hudson Jeans
Tights: HUE

How to wear maxi with ankle boots How to style ankle boots maxi

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.

Your turn…

Which outfit is your favorite?  Have you been hesitant to try ankle boots or do you already have a pair that you love?

Linked-up with: Fun Fashion Friday|Shoe and Tell

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  • Reply Stephanie September 27, 2015 at 10:08 pm

    My favorites are the boots paired with the sweater dress which is an outstanding classy look but I also liked the long dress as vest also. The dress/vest was visually interesting and fun. I would just button one more button on top if it doesn’t interfere with the necklace which I loved with this look. I did like your plaid shirt with the jeans but I was confused by the skinny jeans look. We’re the skinny jeans tucked in the boots? Or rolled up I was trying to tell bc I want to wear my skinny so w/ my short boots too. Overall all 4 looks were great. I love wearing my ankle boots and I especially love them with dresses and tights. That look I find so fashionable for some reason

    • Reply Tall Fashion Adventures September 28, 2015 at 1:07 pm

      Why thanks! Happy to hear your ideas. My black skinny jeans are rolled up so they hit just above the top of the boots. Hard to tell from the photos. I’m trying to remember what ankle boots you have. You’ll have to show me.

  • Reply karen September 28, 2015 at 8:58 pm

    Very nice booties! 🙂
    Look 2 is defo my fav! That dress looks sooooo comfi, and it’s the perfect look for fall.
    Obviously, look 1 is very nice too, great top!! 😉
    Look 3 is a bit lumberjack-y indeed, but I think that fits this time of year perfectly. Not sure if I’d wear it in summer though…
    Look 4: like you, I am not sure. I like how you’ve paired your maxi dress with the mini-dress underneath though. Maybe it works just a bit better with black booties?

    Great find for the season though!

    • Reply Tall Fashion Adventures September 30, 2015 at 5:30 pm

      Thanks! A 20-something German girl that I walked by on the street told me she really liked them and asked me where I bought them. It made my day! 🙂 I love look #2 as well and can’t wait to wear it out. I think you’re right re look #4 – maybe black ankle boots are better.

  • Reply Allison @ The Tall Mama September 30, 2015 at 6:02 am

    I love how you’ve styled the boots! I have that style of boots and they are timeless. x Allison

    • Reply Tall Fashion Adventures September 30, 2015 at 6:50 pm

      Thanks Allison! They do indeed seem timeless which makes me happy. A stranger stopped me on the street today and asked where I got my boots which made me quite happy. 🙂

  • Reply Sara October 1, 2015 at 12:53 pm

    I am a big fan of ankle boots – they’re just so comfy and easy to wear. I like them best with the 2 dresses but all 4 looks are great for Autumn.

    I’ve never heard of ‘Chelsea’ boots before though – if you’d shown me a picture of these and asked me to describe them I’d have told you they were jodhpur boots, for riding! (Like these: Oops!

    Great post!
    Sara x

    • Reply Tall Fashion Adventures October 2, 2015 at 11:00 pm

      Yes! You’re right! They are super comfy and easy to wear. I had never heard of Chelsea boots before this year either but now I’m hooked. I can see what you mean about them resembling jodhpur boots. Very interesting.

  • Reply Jill October 2, 2015 at 1:06 pm

    Those boots are so cute! I love all of the ways you styled them! They look great with the dresses!

    Doused In Pink

    • Reply Tall Fashion Adventures October 2, 2015 at 11:00 pm

      Thanks so much Jill! I love them with the dresses too.

  • Reply Dawn Lucy October 3, 2015 at 4:43 am

    All great looks and I totally wanna copy that maxi dress outfit! Bravo!

    Thanks so much of sharing with Fun Fashion Friday & hope you have a great weekend!
    Dawn Lucy

    • Reply Tall Fashion Adventures October 7, 2015 at 2:54 pm

      Thanks so much Dawn Lucy! If you copy the look, I want to see! Hope you had a good weekend too.

  • Reply Jaymie Ashcraft October 3, 2015 at 2:44 pm

    Great booties!!! Love with the black dress.
    Fridays Fashions link up love for you to join. 🙂

    • Reply Tall Fashion Adventures October 7, 2015 at 2:54 pm

      Thanks so much Jaymie! I think I’m going to wear the black dress/booties combo this weekend.

  • Reply Another Tall Blogger Meet-Up! October 16, 2015 at 4:12 pm

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  • Reply Andrea@WellnessNotes October 16, 2015 at 5:44 pm

    I love the boots with all four outfits! And thanks for the lesson on Chelsea boots; I don’t think I had ever heard of them (or, probably, I just didn’t pay attention….).

    #4 would also be out of my comfort zone, but I think it’s fun and looks great!

    • Reply Tall Fashion Adventures October 16, 2015 at 6:39 pm

      Thank you! Now that I have a pair and have learned about them, I see Chelsea boots everywhere. Funny how that happens, isn’t it?

  • Reply My Love Affair With Tall Blazers - Long Tall Sally Riding Jacket April 16, 2016 at 8:17 pm

    […] guess you could say I’m a bit Long Tall Sally’d out in this look since the lace top and Chelsea boots are also from LTS (both c/o). I’m really liking the romantic-ish combo of the lace and light […]

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