How to Style: Chelsea Boots

For When You’re Stepping Out

ASKED & ANSWERED

Last month’s blog featured a high-low selection of quality Chelsea boots. You may have invested in a new, reliable pair this season, but the question that keeps coming up from female clientele is: How do I style my Chelsea boots? Here are 4 ways to wear this reliable winter lug sole without having to think about it again.

Shop THIS LOOK:

• L.L. Bean Women's Bean's Sherpa Fleece Jacket, shown in Vintage Indigo — Sizes XXS-XL. Multiple colors available. $99

• Theory Intarsia Cashmere Sweater — Sizes XS-L. $395

• Nili Lotan Cropped Military Pant, shown in Henna — Sizes 00-12. Multiple colors available. $325 (some colors on sale)

• Parcours XL Palais Royal Tote, shown in Camel/Choco.

• Falke Sensitive Malaga Crew Socks, shown in Sand — Sizes US 4-11. Multiple colors available. $27

• Stella McCartney Trace Chelsea Boot, shown in Cream — Sizes US 5-11. $725

STYLE TIP:

A higher shafted Chelsea boot pairs well with these cropped military jogger style pants. An alternative to denim and even more comfortable in their soft cotton. Add thick socks and pull them up underneath the pants for when you’re seated and the pants raise slightly to avoid exposing skin to the cooler weather.

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Shop THIS LOOK:

• Demarson Mini Pave Luna Earrings in Shiny Gold and Crystals, for pierced ears. $175

• Jenni Kayne Cocoon Cardigan Sweater, shown in Ivory — Sizes XXS-3XL. Multiple colors available. $445

• Enza Costa Silk Ribbed Long Sleeve Tee, shown in White — Sizes XS-L. Multiple colors available. $110.40

• Spanx Faux Leather Leggings, shown in Black — Sizes XS-3XL and in Petite, Regular & Tall. $98

• Gianvito Rossi Chester Calf-Hair Chelsea Boot, shown in Leopard Calf — Sizes US 4-12 (some sizes sold out). $1,495 now $747

STYLE TIP:

Tuck the leggings smoothly into the shaft of the boot - the stretch gator sides on this style will make room for thin leggings and thin socks underneath — this elongates the leg. Add a cardigan that will cover your bum so you can confidently strut around in this cozy-chic style.

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Shop THIS LOOK:

• Lescarf No.2 Striped Silk-twill Scarf, shown in Black/White — One size. $86

• Khaite Lise Sateen Slip Maxi Skirt, shown in Ochre — Sizes 0-10. $681

• Stand Studio Vida Faux Leather Bucket Hat, shown in Black — Sizes S-M. Multiple colors available. $105

• La Ligne Stripe Cashmere Sweater, shown in Black/Cream — Sizes XS-XL. Multiple colors available. $295

• Loeffler Randall Bridget Chelsea Boot, shown in Black — Sizes 7-12. $395

• Commando Very Fine Fishnets, shown in Black — Sizes S-L. $36

STYLE TIP:

Dress up or wear a silk skirt for everyday. Layer over pantyhose or thick socks so you don’t get too chilly. These LF Chelsea boots make for great pairing with thin or thick tights thanks to their stretch ankle gator (I like a fishnet, personally). BONUS — If your skirt is too long, considering shortening a silk skirt to be a mid-calf length (an easy, affordable alteration) to show off your boots and make this a year-round style.

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Shop THIS LOOK:

• Wolford Colorado Stretch-jersey Turtleneck Thong Bodysuit, shown in Ivory — Sizes XS-L. More colors available. $250

• Isabel Marant Étoile Fontiali Coat — Sizes S-L. $830 now on sale $498

• Shrimps Carola Striped Alpaca-blend Beanie Hat — One size. $270

• MOTHER The Hustler Ankle Fray, shown in Home Movies Wash — Sizes US 23-33. More colors available. $228

• Christian Louboutin Marchacroche Leather Ankle Boots, shown in Black — Sizes US 4-11. $995

STYLE TIP:

A little kick crop denim is the perfect cut to show off an ankle bootie. Tuck your denim over the top of the booties and the crop flare with flatter anyone. Style with an oversized shirt jacket and a tucked in bodysuit and step out in stylish comfort.

Affiliate Disclosure: I occasionally use affiliate links, which means that if you make a purchase, I may receive a small commission. This is at no cost to you. Thank you for continuing to support my work!

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