Chelsea Boots Five Ways

I love a pretty suede or leather pointed toe pair of boots, but sometimes you just need function. In comes a water-resistant pair of chelsea boots.

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My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). 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. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.

The boots I chose for this post are an under $100 option from Nordstrom. The boots are water-resistant and start at a size 4 (yay for extended sizing). They have a classic round toe and a chunky block heel.

Sizing: I find the boots to run 1/2 size large, but I would stay with your true size so you have room for thick warm socks.

How to Style Chelsea Boots

Styling a round-toe chunky pair of boots isn’t always seamless for someone who is petite. Since the shape of the boots can make you look a little bit shorter and off-balance here are a few things I keep in mind when styling them:

Shaft Width & Height: Just like with other boot styles, I think a pair of boots with a slim tall shaft that fits close to your ankles and slides under your jeans is a good choice. The pair I chose for this post has a nice balance.

Styling with Jeans: When chelsea boots started out in popularity we most often wore them with skinny jeans. You can absolutely still wear them that way, but for an updated look try a pair of straight or cropped flare jeans that have a wide bottom so they easily slide a little bit over the boot shaft without catching. I styled them in this post with a straight style and a cropped flare style. The only denim styles I would avoid with chelsea boots are full-length styles (i.e. wide-leg, flare, full-length straight). The boots are too heavy and chunky for a pair of jeans that cover them. A cropped style still shows the slim shaft/your ankle so the pairing doesn’t look as chunky.

Choose High-Rise Jeans: Choose jeans that rise to your belly button/natural waist to help lengthen your legs. For some petites that is a pair of true high-rise jeans and for others it’s a mid-rise.

Avoid High Contrast Bottoms: To reduce the leg shortening effect chelsea boots can have, pair them with jeans that are dark or black (if your chelsea boots are black). Anything high contrast will chop you off at the ankles visually.

What to Wear on Top: I think chelsea boots look best with a top that creates balance. Since the boots are chunky, a heavy top is your best bet. Some examples of what I consider to be a heavy top are chunky sweaters, coats, and vests.

Other Bottoms: Chelsea boots also pair easily with leggings, and tights with skirts and dresses. If you choose to wear them with a skirt or a dress I recommend choosing a style that is above the knee.