The Essential Guide to Styling Boots
Boots are a staple in every woman’s wardrobe. They’re always fashionable and endlessly comfortable. A great pair of boots can take you from work to errands to a nice night out with just a few small outfit tweaks. What more could you want?
If you’re ready to incorporate boots into your OOTD, we’re here to help. Read on for our essential guide to styling boots for every season, every occasion, and every body type.
Boots 101: Know Your Styles
The world of boots is expansive, with a range of styles to satisfy just about everyone. Before diving into how to style boots with jeans, let’s start with the basics. The most common styles of women’s boots include:
Ankle Boots: Named for their height, ankle boots hit right at the ankle for a versatile and flattering fit. These shoes are perfect for casual to business-casual outfits and a great choice in warmer weather.
Knee-High Boots: Knee-high boots offer a much more dramatic look. They reach just below the knee for a chic fit that pairs great with skirts and skinny jeans.
Over-the-Knee Boots: The boldest fit on our list, over-the-knee boots hit at the lower thigh, just above the knee. They’re trendy, a little sexy, and perfectly warm for fall and winter layers.
Combat Boots: For something that’s totally edgy while still practical, try a combat boot. These chunky, military-inspired boots provide all-day comfort. Balance them with more feminine pieces for eye-catching contrast.
Chelsea Boots: A classic and timeless style, Chelsea boots hit at the ankle and feature an elastic panel on the side for easy ins and outs. These simple boots are ideal for minimalist wardrobes.
Western/Cowboy Boots: A Western-inspired boot is a great statement piece that can add fun and excitement to an outfit. Just be sure to pair them with something simpler to avoid veering into costume territory.
How to Style Boots for Every Lifestyle
Now that you’ve got the basics down pat, it’s time to have fun! Read on to learn how to style boots for every lifestyle and occasion.
Keeping It Casual
If you’re looking to add a touch of sophistication to a casual outfit, swap out your sneakers or sandals for a pair of boots. Stick to ankle boots in combat or Chelsea styles to keep it laid back. Use these outfits to inspire you:
Outfit Inspo #1
Pair a brown leather Chelsea boot with your favorite skinny jeans in dark denim. Add a chunky, cozy sweater and finish the look with a purposefully messy bun.
Outfit Inspo #2
Dress down your favorite knee-length, casual dress with a pair of combat boots. Pick a dress that’s soft, feminine, and flowy to add exciting contrast to the boots.
Work the Boardroom
Next time you’re at the office, ditch the heels and select a great pair of boots instead. You’ll look chic and stylish—and your feet will thank you! Here’s how to style boots with your modern, business casual wardrobe for professional, sophisticated style:
Outfit Inspo #1
Wear a sleek, black ankle boot with a slim-fitting trouser to give the appearance of legs for days. Rather than a boring button-up, select a satin blouse in a jewel tone and finish the look with a fitted blazer.
Outfit Inspo #2
For a look that’s professional with a touch of sass, pair an above-the-knee skirt with your favorite ankle boots. Add a bit of modesty with a pair of tights and finish the look with a simple turtleneck.
Nail the Night Out Look
Boots add the perfect amount of cool and sultry energy to your night-out look. Try some of these ideas for your upcoming occasion:
Outfit Inspo #1
Put a Western spin on your night out outfit by pairing a cowboy-inspired boot with your favorite bootcut pants. Balance the look with a modern top like a fitted, simple tank or high-neck blouse.
Outfit Inspo #2
For a winter date outfit that strikes the balance between warm and sexy, wear your favorite skinny jeans with an over-the-knee boot. Top it off with a slim-fitting sweater that shows off your physique while still keeping you comfy all night long.
Seasonal Styling Tips
Summer, spring, winter, or fall—there’s a boot for every season. Read on to learn our favorite styling tips to show off your favorite boots year-round.
Spring Boot Styles
Spring is all about transitional style that can keep you comfortable through chilly mornings, warm afternoons, and cool nights—and the occasional rainfall. Style boots with these outfits in your spring wardrobe:
Outfit Inspo #1
Pair a short-sleeve wrap dress with a pair of knee-high, leather boots. On a cooler spring day, add tights for warmth. Finish with your favorite denim outerwear for a cute and stylish springtime jean jacket outfit.
Outfit Inspo #2
Style boots with jeans for spring by wearing a comfy, boyfriend-fit jean that hits just above the ankle with a cute ankle boot. Look for synthetic or leather materials that can stand up to an occasional rainshower. Add a lightweight cardigan over a close-fitting tee to finish the look.
Summer Boot Styles
Think boots are off-limits in summer? Think again. Styling boots with dresses is a great way to stay comfy in boots in warmer weather. It’s also a good idea to look for lighter-weight materials like canvas, perforated fabric, or other breathable options. Check out these ideas:
Outfit Inspo #1
Add a touch of sophistication to a basic, comfy t-shirt dress with a pair of ankle boots. Put your hair in a high pony to keep yourself cool.
Outfit Inspo #2
Make a fashion statement with an open-toe boot that’s half boot, half sandal. Wear with your favorite pair of cut-off shorts and a lightweight, feminine top.
Fall Boot Styles
Fall is the perfect season for comfortable Chelsea boots and knee-high fits. Opt for a darker color scheme to keep your outfits on-season, but don’t be afraid to play with texture. Read on to learn how to style boots for fall:
Outfit Inspo #1
Wear a pair of leather, knee-high boots with dark-washed denim. Add tons of contrast to your sleek, dark bottom half with a creamy, soft, and luxurious sweater on top.
Outfit Inspo #2
For a going-out outfit in fall, add a bit of edge to a slinky, feminine dress with a great pair of combat boots. Add a sheer pair of tights for warmth and tie the look together with a blazer.
Winter Boot Styles
In winter, it’s all about knee-high boots and higher. For snowy and rainy regions, stick to waterproof leather and synthetic boots. When shopping for boots for winter, be sure to leave a bit of room for a thick and cozy pair of socks. These are our best ideas for styling boots for winter:
Outfit Inspo #1
Balance out chunky, knee-high boots with a slim-fitting, fleece-lined pair of leggings. Add a tunic that hits at your upper thigh and a cozy scarf for warmth.
Outfit Inspo #2
Tuck a slim-fitting pair of pants into fur-lined Chelsea boots. Add a warm turtleneck and your favorite peacoat. Finish the look with a matching scarf and beanie, and a warm pair of gloves. You’ll be ready for whatever winter throws at you.
Boots for Every Body: Finding Your Perfect Fit
Depending on your body type, you may find that some boot styles and fits are more flattering than others. Read on to learn how to style your boots to balance out your unique proportions.
Tips for Petite Women
Petite women may find that, if not styled correctly, boots can leave them looking shorter in stature than ideal. Follow these boot styling tips to create an elongated silhouette:
If you find that round or square-toed boots make your legs look stubby, opt for pointed toes to elongate the leg.
Another leg elongating tip is to match your boot color to your pants to give the appearance of length.
Choose a boot that hits right at the ankle or just below the knee or higher. A mid-calf boot can cut your leg off at its widest part.
Styling for Tall Women
For taller women who are concerned about looking too large or disrupting the balance of their proportions, consider these tips for a flattering fit:
Focus on defining the waist with a belt or a fit-and-flare style. This can add a visual break and some additional curve.
Pairing a knee-high or over-the-knee boot with a too-short skirt can look overly sexy. Choose a skirt that hits just below the knee or a midi skirt to keep it flirty but fashion-forward.
Catering to Curvy Figures
Curvy women can look great in boots, too. Read on to learn how to style boots on a curvy body:
If you struggle to find boots that fit your wider calves, look for flexible material like soft leather. A quick trip to the cobbler can also work wonders.
Chunky boots like combat boots may add too much weight, depending on your stature. Look for platform styles to add balancing length.
