Chelsea boots continue to be a popular boot this season for good reason. They’re a great blend of comfort and style with many of them also being weatherproof. However, if you’re petite like me, it can be a little tricky to style them. Today I’m sharing four different styling options with tips and tricks for making them work with different types of jeans and bottoms on anyone – but especially if you’re petite.
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Four Ways to Wear Chelsea Boots
Sizing Reference: I’m 4’10” and my bust, waist, and hip measurements are 32″, 24″, and 36″. My typical inseam is 24″-25″.
I tried a few different brands of chelsea boots before landing on the Cleary Chelsea Boot from Madewell as my favorite. This pair has a slim profile (not a crazy thick sole) and the shaft height is just right (not too tall or short). I bought them in cognac first and loved them so much I went back for black as well. They’re beautifully made and have a classic style that will last for years. They’re true to size.
With Straight Jeans
If you want to wear your chelsea boots with straight jeans, pick a pair of jeans that is long enough for the boots to tuck under. If the jeans are too short it makes for a choppy look. This look also works best if you can find a pair of chelsea boots that fit slim to the ankle. The pair I’m wearing work, but they could be a little slimmer to keep the jeans from catching when I walk.
Boots TTS | Coat Petite 0 | Jeans Petite 24 | Sweater XXS | Socks | Bag
With Skinny Jeans
If you’re wearing Chelsea Boots with skinny jeans, find a pair that meets the top of the boot or you can cuff them just a little as I did here. If I’m wearing a black pair of boots I will also wear long black socks so my ankles don’t show and break up the look. (It also keeps me warm!)
Jeans Petite 24 | Boots TTS | Similar Bag | Sweater Petite XS | Topcoat Petite 00 (updated version) | Earrings
With Leggings
Wearing Chelsea Boots with leggings is one of the easiest ways to wear them. It’s also my favorite way to wear them and one outfit combination I go to often. I see people wear leggings just tucked into the boots (which is how I prefer it) and also with tall socks that peek out of the top of the boot. Since the slim space between my ankles and calves is pretty short, I avoid the addition of chunky socks. Otherwise, it will just create a thick line from boots to calves and make my legs look even shorter.
Boots TTS | Earrings | Sweater Small | Leggings XS Short | Bag
With a Skirt
You can also wear chelsea boots with a skirt or dress – just keep it above the knee if you’re petite. You can swap the opaque tights for sheer tights, or go without them altogether if it’s not cool enough where you live for them. This skirt also comes in other (non-holiday) prints.
Boots TTS | Tights | Earrings | Similar Bag | Sweater XXS | Coat Petite 00 | Skirt 00
-Brooke
