How to Wear Chelsea Boots

Kicking it Comfortably and Casually

Run errands in your boots and comfortable jeans, shorts, or leggings. Chelsea boots are comfortable and versatile so they make an ideal shoe for your on-the-go look. Feel relaxed yet look stylish by wearing any color boot with a t-shirt and your favorite jeans, shorts, or leggings. Pair Chelsea boots with relaxed-fit, bootcut jeans or your favorite comfy leggings for a more relaxed look. While it’s cool to let jeans hang over the top of the boot a little bit, you want the hem of jeans to stop before your ankle. Choose a shorter jean, cuff them, or tuck them into the boot so everyone can see your boots as you walk.

Look great on a day-date in your boots and a nice shirt or fun dress. For a picnic in the park or a stroll around the farmer's market, wear your Chelsea boots with a short, flirty dress or a nice pair of pants and button-up shirt. Black Chelsea boots will make your outfit look dressier, while tan or brown boots will add a casual touch. Tan or taupe Chelsea boots pair perfectly with a flowy, short Boho dress. In the fall and winter, complement your jeans and boots with a sweater and a blanket scarf.

Head to work in Chelsea boots, trousers or a pencil skirt, and a jacket. Suede and leather Chelsea boots look great with your favorite work clothes. Wear the boots with chinos or a pencil skirt and tights, along with a fitted jacket, and you will have a polished and professional look that will turn heads. Create a classic business casual look with brown leather Chelsea boots, khaki chinos, a white oxford, and a blue blazer. Or jazz up your look with black matte leather Chelsea boots, a bright patterned shirt, a contrasting light blazer, and dark pants. Chelsea boots also look professional and trend-savvy when worn with a dressy tunic or blouse, opaque leggings, and a matching scarf. Brown Chelsea boots are so versatile, you can wear them with khaki, navy, olive, or tan trousers.

Accessorize casually with a light sweater and understated jewelry. Add a thin cardigan or flannel shirt, a pair of aviators, and a long pendant necklace to your outfit for cooler weather. Or toss on your favorite hoodie or jacket and go out in comfort and style. Don't go overboard on accessories when you are going for a casual look. Keep in mind your planned activities for the day and dress for comfort according to what you will be doing.

Dressing up for Stepping Out

Pair your boots with skinny jeans and a scarf for a smart, trendy look. Turn heads on your next night on the town with a pair of black leather Chelsea boots and black skinny jeans. Top it off with a black roll neck sweater or a leather moto jacket and a scarf that tells everyone you came for the party. Skinny jeans look great with tucked into the top of your Chelsea boots. You can wear suede, matte leather, or patent leather Chelsea boots for a night on the town, depending on how dressy you want to appear.

Dress up with patent leather boots and a suit or a little black dress. The key to looking trend-savvy in Chelsea boots and a suit is fitted pants. You’ll want a nicely fitted suit with narrow leg openings to look tall, lean, and fashionable. To look amazing in your little black dress, wear black tights and black boots to create a monochrome look that makes you look long and lean. Pair black and grey suits with black leather boots and black or brown boots with navy and brown suits. Your pants should extend just a few centimeters over the top of your boots when standing. You want most of the boot to show as you walk.

Finish off your outfit with nice jewelry and matching accessories. To dress up your outfit, add jewelry like a nice watch, sparkly earrings, or a fancy necklace. Little accessories like pocket squares, matching suspenders, and leather belts that match your shoes really add polish to a dressy outfit. Don't underestimate the accessorizing power of one or two great items. A normally drab outfit can be made into a wow ensemble with a posh bag or a big statement brooch or necklace. If you are trying to keep it professional, keep flashy accessories to a minimum. But for a night on the town, feel free to add pizazz.