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Celebrity Stylist Shares the Best Outfits With Boots That Work for Any Occasion

Here, 6 complete looks for how to style a pair of boots you already have in your closet

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When it’s warm outside, we always slip into a pair of sandals or flip-flops to run out of the house. And once it gets a tad chillier, we opt for closed-toe shoes like comfortable flats. But now that we’re bracing for cooler temperatures, the go-to shoe year after year during the colder months is a pair of boots. From ankle booties to mid-calf and knee-high boots, the shoe style is a staple item in every woman’s wardrobe. And it’s possible that you already have a few pairs but aren’t sure how to style them or you’re looking for new ways to wear them. Maybe you’re in the market for a new pair of boots — no matter the case, we turned to celebrity stylist Eric Himel for the best outfits with boots that will have you feeling great and turning heads.

What to look for in a pair of boots

Amanda Holden wearing tall brown boots

When it comes to selecting a pair of boots, there are a few key things you should look for:

1. Keep comfort in mind

Long gone are the days of slipping your feet into uncomfortable, painful heels or boots just for the sake of fashion. There are many options on the market today that are both comfortable and stylish, ensuring your feet are pain-free all day. For added comfort, look for soles that are cushioned or padded for additional support.

2. Make sure the heel is sturdy

The height of the heel on a boot is completely up to personal preference. But no matter how high or short, you want something that is sturdy and stable. This doesn’t mean you have to choose chunky, block-heel boots — it just means that if going for a thinner heel, make sure it feels secure enough to the sole and isn’t so skinny you’re going twist your ankle. That’s why stylists like Himel advise doing a test walk around the house before venturing outside in pair of boots.

Allison Williams wearing black boots
James Devaney / Contributor

However, you don’t want to completely ditch the heel when it comes to picking out a boot. “When buying a flat boot, avoid totally flat ones to not appear elfin, and opt for one with a ½” heel instead,” adds Himel.

3. Choose a pair that’s versatile

While a bold, brightly hued pair of boots is always fun once in a while (see below for a vivid red pair), overall, it’s best to choose a pair that you can wear with almost any outfit. If you tend to wear more blacks and darker colors, opt for a pair of black boots. And if you wear more browns and tans, consider brown boots. Himel says it’s great to have one pair of each (black and brown), but boots that work well with the color scheme you wear most is a good place to start.

6 outfits with boots for every occasion

Keep reading for outfit inspiration for your favorite pair of boots or shop our favorite boot finds below.

1. Outfits with boots: For an office party

Brown boots outfit

For a more dressy professional outfit, a sweater dress paired with tall brown boots is the perfect pairing. This cozy sweater dress from Express features a tie belt around the midsection to carve out curves. And slipping into a pair of brown boots that hit below the knee will not only keep you warm, but create the illusion of longer legs by drawing the eye upward. Plus, tall boots are all the rage right now, says Himel. “I am loving that knee-high boots are finally back! They are so versatile and work on women of all ages.” 

Tip: If leg skin is exposed between a dress or skirt and boots, Himel advises wearing a pair of tights to keep the eye scanning vertically. For the perfect finishing touches, tying in the chain link accent on the boots with a chain link bracelet and necklace adds pretty pizzazz. And wearing a brown, leather shoulder bag coordinates with the boots for a chic, cohesive look.

Shop the look:

Tall brown boots: Buy from Macy’s, $50.12

Cream sweater dress: Buy from Express, $64.80

Brown leather bag: Buy from Amazon, $22.49

Gold chain link bracelet: Buy from Altar’d State, $24.95

Gold chain link necklace: Buy from Banana Republic Factory, $24

2. Outfits with boots: For running errands

Outfits with short fuzzy boots

If you’re out and about shopping or running a few errands around town, comfort is key. And these suede and sherpa ultra-short booties are like a comfy pair of slippers. But they look more polished than slippers and are so easy to slip on and run out the door. Wearing with a cream puffer vest that stops at the hips keeps you warm without adding bulk to the body. To finish off the look, a plain brown long-sleeve body suit, light-wash jeans and cream socks are sure to leave you looking put-together when on the go.

Shop the look:

Short tan suede booties: Buy from Target, $30

Brown long sleeve bodysuit: Buy from Old Navy, $14

Light wash straight leg jeans: Buy from LOFT, $89.95

Cream puffer vest: Buy from Amazon, $29.97

Cream knit crew socks: Buy from Amazon, $16.99

3. Outfits with boots: For a happy hour

Red boots outfit

“I love a heeled boot with a dress or skirt,” says Himel, and we agree! This outfit makes a stunning statement when meeting up with friends or coworkers after hours. A pair of tall, red boots draw focus to the legs. And tying in the pop of red with a matching red sweater keeps the look polished, while pairing it with a black leather midi skirt and leather jacket balances out the bold color. What’s more, a simple pair of chunky silver earrings frames the face no matter if your hair is up or down.

Shop the look:

Red tall leather snake skin boots: Buy from Lulus, $49

Red mockneck sweater: Buy from White House Black Market, $59.40

Black tie belt leather jacket: Buy from Gap Factory, $82.80

Black leather midi skirt: Buy from J. Crew, $74.50

Silver chunky teardrop earrings: Buy from Amazon, $12.78

4. Outfits with boots: For a daytime gathering

Outfits with brown booties

Chelsea boots have been around for decades, and for good reason. And a pair that has a chunky block heel like the one above makes for long-lasting comfort and extra stability. Plus, they’re not too dressy or too casual — you can dress them up or down. Even better? A pair that features both black and brown pairs with everything in your closet.

For a polished yet casual look, throw on a black sweater (one with balloon sleeves gives a plain sweater some fun flair) and medium-wash jeans. And accessorizing with gold jewelry like earrings and a watch makes skin look glowing, while a reversible belt (that’s black on one side and brown on the other) cinches the natural waist.

Shop the look:

Brown and black leather booties: Buy from DSW, $109.99

Black balloon sleeve sweater: Buy from Amazon, $32.76

Medium wash high rise jeans: Buy from H&M, $39.99

Black and brown reversible belt: Buy from Amazon, $16.99

Gold and black watch: Buy from Amazon, $65

Gold hoop earrings: Buy from Amazon, $12.99

Julianne Moore wearing black boots

5. Outfits with boots: For a girl’s night out

Outfits with black boots ideas

For a fun night out with girlfriends, a heeled black boot is a great option with dark-wash denim, which Himel says will make legs appear longer. The flare at the bottom of these jeans balances out wider hips and a pair with a high waist optically elongates the lower half. For the top, a square-neck gray sweater shows off a tasteful amount of skin and keeps you cozy if you go to separate spots for dinner and drinks. And a pink crossbody purse adds a fun pop of color to the look, while a silver knotted necklace and drop earrings add a touch of sophisticated sparkle.

Shop the look:

Black leather boots: Buy from Aerosoles, $39.99

Dark was bootcut jeans: Buy from LOFT, $89.95

Grey square neck sweater: Buy from Venus, $32.99

Silver double chain knot necklace: Buy from Amazon, $8.99

Silver knot drop earrings: Buy from Revolve, $41

Light pink crossbody purse: Buy from Amazon, $22.99

Related: The Most Figure-Flattering Ways to Style Flare Jeans for Any Occasion

6. Outfits with boots: For a day at work

work outfit with boots

If you can’t wear jeans at work, don’t worry! You can effortlessly pair ankle booties with your favorite dress pants. These pants from Lane Bryant are a great plus-size option and feature pretty gold buttons on the front pockets, which perfectly match the gold zipper of these booties. And a tie-neck blouse is not only chic but also trims visual inches from the torso. To tie the look together, a gold necklace and earrings coordinate with the other gold accents and bring attention to pretty facial features.

Shop the look:

Black ankle booties: Buy from Amazon, $39.99

Black dress pants with gold accents: Buy from Lane Bryant, $79.95

Blush tie neck blouse: Buy from Express, $34.80

Gold necklace: Buy from Amazon, $24.89

Gold earrings: Buy from Amazon, $9.50

For more fashion inspiration, click through these stories:

7 Midi Skirt Outfits For Every Occasion From Errand-Running to Cocktail-Sipping

The Most Figure-Flattering Ways to Style Flare Jeans for Any Occasion

‘I’m a Podiatrist and These Are The Most Comfortable Flats for Women Over 50’

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