Daily Drills Loungewear: Playful Shorts, Fleece Crews and Easy Pants

Daily Drills began with two best friends noticing the same thing: the everyday wardrobe had gaps, and getting dressed could use a little more joy. Los Angeles-based founders Kennedy Crichlow and Mary Ralph Bradley started the brand in 2020, bringing their shared entrepreneurial energy to a label built around daily dressing. Crichlow’s path included startups and marketing, while Bradley grew a social media following and worked with fashion and beauty clients. I like that the punctuation is practically a point of view: the exclamation marks stand for enthusiasm, not a solemn uniform. The result is a lifestyle brand that wants ordinary dressing to feel like a small event.

 

The founders first imagined an activewear label, then realized the bigger idea was clothing for the different stages of a day. In an interview with VIE, they describe designing pieces to move through those moments; the brand’s own story ranges across loungewear, workout apparel and vacation-minded resort wear. That makes shorts, crews and pants a convincing little wardrobe of their own, each answering a different mood without losing the cheerful, slightly sporty character. The appeal, to me, is permission to dress for the whole day, not only the polished hour. I’d treat Daily Drills as a good fit for someone who enjoys color, graphic details and relaxed dressing. If your ideal closet is strictly formal or spare, its high-energy language may feel like too much.

The shorts selection is less about one uniform than choosing a mood. Thermal Boy Shorts at $55 feel like a clever start to a slow morning, while Sherpa Micro Shorts at $75 are the kind of shorter silhouette I’d balance with an oversized crew. Sporty Shorts, also $75, give me the more athletic direction; I’d keep the rest of the outfit clean, perhaps a plain tank and low-profile sneakers, so the color or shape gets to lead. The useful thing here is the range: you can stay close to lounge dressing or let the pair set the tone for a full errands-day outfit.

 

Striped Cotton Shorts ($80) and Ribbed Knit Shorts ($90) bring pattern and texture into an easy tank-and-sneakers combination, while Raw Hem Super Shorts are my pick when the look wants a little rough edge. Fleece Bermuda Shorts and Cashmere Micro Shorts offer two very different answers to coverage, one longer and one intentionally short. I’d choose a roomy top to balance the abbreviated pairs and keep a crisp shirt ready for the striped option. If you’re building a small capsule, start with one simple pair and one playful pattern, then add the pair that feels like a treat. That mix keeps the shorts from reading as one-note gym gear.

The crews and hoodies are the cozy center of this edit, the pieces I’d grab when a day begins early and the plan is still taking shape. Fleece Raglan Crew at $125 is a straightforward layer to build around; Oversized Fleece Athletics Crew, also $125, gives me a more graphic, team-sweatshirt mood. For an easy set, I’d pair either with shorts from the first section and let the top carry the color. Daily Zip Hoodie at $125 adds a zip-front option, useful for airport mornings or the walk that starts chilly and warms up.

 

There’s also a good run of character pieces. The Oversized Lucky Crew and Vintage Crew are the fun choices when I want a sweatshirt to feel personal, so I’d wear either with quiet pants rather than adding more graphic noise. Heavyweight Funnel Neck Daily Quarter Zip at $130 is the more directional layer, while Cashmere Double Zip Hoodie at $150 makes the zip itself the feature. They also connect the playful shorts to the softer pants elsewhere in this edit. For sizing, I’d decide first whether I want a close layer or a deliberately roomy silhouette, then use the size guide to settle on a fit. This is cheerful casual dressing, not a substitute for sharp tailoring; if you like your weekend layers expressive, start with the crew that feels like you.

Pants and sweatpants set the low-key pace, and I like that the edit moves between resort stripes and track-inspired ease. Thermal Resort Pants at $90 sound like a natural match for a slow morning or a travel day; I’d wear them with a simple fitted tank and carry a crew for the ride. Striped Cotton Pants, also $90, feel more like a scene-stealer with a plain sweatshirt and flat sandals. The stripes can do the talking, so I wouldn’t add another pattern. This is the kind of relaxed dressing that makes room for an unplanned coffee stop or an early flight.

 

First String Pants at $95 are the sporty middle ground I’d reach for when I want an outfit to feel put together without leaving the comfort-first lane. Lightweight Scuba Track Pants at $110 make the most athletic case, and I’d pair them with a zip hoodie rather than trying to style them as office trousers. This category makes sense for someone who wants an off-duty uniform with personality, especially when the week includes errands, flights or a long coffee stop. I’d start with the cut and color I can picture wearing twice in a week, then use the size guide for the fit I prefer. If precise tailoring is the goal, look elsewhere; the charm here is relaxed dressing with a wink. It rounds out a wardrobe made for moving between lounging and plans.