Fall Boots Series: Chelsea Boots

In this part of the fall boots series, I’m styling a pair of comfortable flat chelsea boots in three different ways.

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Fall Boots Series: Chelsea Boots

My Sizing: I’m 4’10” and my bust, waist, and hip measurements are 32″, 24″ and 36″. My typical inseam is 24-25″. The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online.

Chelsea Boots

For the post, I chose a pair of slim chelsea boots from J.Crew Factory. They’re comfortable and overall true to size. What I like about them is the taller slim shaft and squared-off toe. It gives them a sleek look that’s easy to wear in many different ways. If you prefer a more casual pair I also love this pair from Madewell.

With Jeans

If you want to wear jeans with chelsea boots I recommend a pair that is wider at the bottom so the boots can easily tuck underneath. The pair I’m wearing here is a cropped flare style, but an ankle straight also works well. I’ve tried these boots with full-length straight jeans and it looks heavy overall, so I think a little crop on your jeans helps. You can also wear them with skinny jeans but meet the hem of the jeans to the top of the boot shaft or if the bottom of your jeans is skinny enough they can tuck into the boots. There are a few examples in this post from last season (this post also gives you a look at the Madewell boots on).

Outfit ideas with chelsea boots via pumps and push-ups blog | petite style blog | winter outfits | petite fashion | chelsea boots

With Leggings

I mostly wear chelsea boots with leggings. I wanted to show different ways to wear them with this post, but I feel the most comfortable in them if I can create balance with the slim look of leggings since they’re so heavy on the foot. I chose a pair of leather leggings for this post, but they also work well with casual leggings.

Petite friendly ways to wear leggings with chelsea boots | chelsea boots outfits | leather leggings outfits | fall outfits

With a Skirt

You can also wear chelsea boots with a skirt! Although I see people wearing them without tights, I appreciate how the tights (sheer or opaque) cut back on the contrast between the boots and my skin which helps with leg lengthening. I would also wear this look with a short skirt, anything too long and it will make your legs look short.