Denim Styling For Any Occasion, From Work to Date Night

Old Navy's High-Waisted O.G. Loose Cut-Off Jeans ($50) are the brand's most effortlessly cool denim offering. The relaxed fit and true-blue wash bring to mind '90s off-duty supermodel style. We like the idea of pairing them with a similarly simple and chic top, such as the Reformation Brenda Linen Top ($148). Channel a vintage, sporty look with your accessories to offset the delicate femininity of the corset top. We suggest the Reebok Club C 85 Vintage Women's Sneakers ($85) and a cute Frankie Shop baseball cap ($36). As the temperatures cool down this fall, add an oversized trench-style jacket.

When it comes to making denim work for the office, bootcut jeans in a crisp, dark wash are our go-to. They have a polished vibe, and they pair well with heels and – of course – heeled boots. Style the Old Navy Mid-Rise Kicker Boot-Cut Jeans ($40) with the Allsaints Aleida Tri Blazer ($179). You can wear the blazer with any basic top of your choice, but we suggest a white high-neck tank top or crewneck tee. Avoid a collared button down, which would be overkill with the jacket. Make a strong statement with the pointy toe and spike heel of the Stuart Weitzman Stretch Booties ($595).

The Old Navy Extra High-Waisted Button-Fly Sky-Hi Straight Cut-Off Jeans ($50) are the ideal jeans for dressing up. They're not too skinny or too baggy, plus the cropped length is perfect for showing off fun high heels. Wear these bottoms with the LoveShackFancy Vima Crop Top ($295) and go all in on playful accessories. We absolutely adore the throwback sensibility of the Circus NY Miranda Heels ($90) in silver. Finally, match the turquoise embellishment of the top with the By Far Dulce Azure Suede Shoulder Bag ($575). All that's missing is an Aperol spritz!

Flattering, flirty, and flared, the Old Navy Higher-High Waisted Cropped Flare Jeans ($55) are the jeans you'll want to choose for your first date with a Hinge hottie. On top, a coordinating sweater set will look stylish without seeming like you tried too hard. Layer the Jonathan Simkhai Kayla Compact Rib Cropped Cardigan ($275) with the matching bra top ($185). We're into heeled mules with this fit, such as the Schutz Posseni Leather Sandals ($118). Complete the look with a shoulder bag and your hair twisted into a claw clip.

The Old Navy Slouchy Straight Black-Wash Workwear Non-Stretch Jean Overalls ($60) are about to become the most worn piece in your closet. For a Sunday Funday with your squad, wear them over the Ganni Seersucker V-Neck Blouse ($215). As for shoes, the Loeffler Randall Leonie Ochre Ballet Flats ($250) would add a subtle pop of color to the outfit. These flats are so comfy, you won't want to take them off.