Jeans, sweater, booties, repeat. If you don't push yourself beyond this tried-and-true combination, fall dressing can get old... fast.
Don't get us wrong — there have been many a chilly autumn morning when that's the exact outfit we reached for. But, if you really want to wear your ankle boots all season long without getting sick of them, you'll have to get a little more creative with your ensembles. Fortunately, a versatile bootie can finish off a variety of different looks, whether you play with proportions and pair them with a contrasting midi-skirt, or you match them with long, loose silhouettes.
To give this go-to shoe the attention it deserves, we're showing you five fresh ways to wear the pairs you already own (with a few shopping suggestions in case you're looking to score a new option, or two). Booties were made for walking (yup, we went there), so stride right into one of the solid outfits, ahead.
Black booties don't just look good with ripped jeans and rocker tees. For a different feel, pair your old-reliable pair with a blush-colored, pleated skirt and a silky blouse. Then, play up the edgy side of the boot with some tough accessories, like a studded crossbody and quirky hoop earrings.
Zara Medium Heel Zipped Ankle Boots, $179, available at Zara; Farrow Elena Pleat Skirt, $ 58 $33.99, available at Need Supply; Aritzia Pozzi Blouse, $110, available at Artizia; N + A Diamond Open Hoop Earrings, $437, available at Catbird; Nadia Gabriella Chloe Shoulder Bag, $650, available at Runway2Street.
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Give these casual booties a polished feel with a high-collared knit tank, dark-wash denim, and a minimal gold bangle. The leather and wool contrasting backpack rounds out the neutral look.
KEEN Morrison Mid Boot, $150, available at KEEN; Ganni Francis Top, $62.99, available at Need Supply; Mango Contrasting Backpack, $39.99, available at Mango; Won Hundred Patti Skinny Jean, $205, available at The Dreslyn; Whistles Inset Stone Bangle, $45, available at Whistles.
Try the dress-over-pants vibe by layering a longline tunic over a pair of cropped, flared jeans. To give this look a more retro feel, opt for some suede booties, cat-eye sunglasses, and a vintage-inspired embroidered pouch.
Topshop Wide Leg Jeans, $75, available at Topshop; H&M Satin Shirt Dress, $59.99, available at H&M; Rochas Embroidered Sac Bag, $1,095, available at ShopSuperStreet; Mango Lace-up Leather Boots, $129.99, available at Mango; Retrosuperfuture Drew Brigitte Sunglasses, $209, available at Farfetch.
Since ankle boots can feel (and look) pretty plain, let that be an excuse to get creative with the rest of your outfit. Even with a silver pair, try a louder pant and a graphic tee. Then, some equally-as-loud accessories, like a spotted clutch and gold ear jackets, top things off perfectly.
Rachel Comey Tilden, $495, available at Rachel Comey; Adidas Originals Graphic T-shirt, $19.99, available at Foot Locker; Hillier Bartley Paisley-jacquard Silk Track Pants, $925, available at MatchesFashion; Clare V. Foldover Clutch, $235, available at Clare V.; Forever 21 Round Ear Jackets, $3.90, available at Forever 21.
Show a little leg while you still can by pairing a printed ankle bootie with a long-sleeved dress that's simple in color, but not silhouette. Throw some innovative-yet-minimalist accessories into the mix, like a dainty ring and clear glasses, and you're good to go.
Loeffler Randall Isla Slim Ankle Bootie, $550, available at Loeffler Randall; Marques'Almeida Denim Mini Dress with Frayed Hem, $365, available at Browns Fashion; Charles & Keith Fringe Crossbody $63.90, available at Charles & Keith; EyeBuyDirect Fitzgerald, $32, available at EyeBuyDirect; A.M. Thorne Double Band with Diamonds, $725, available at Local Eclectic.
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