5 Timeless Outfits For The Working Woman


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Women don’t get enough credit from the working mom to the corporate career woman. Even stay-at-home mothers are always contributing to their households. The last thing most women working tirelessly think about is what they are going to wear for the day, let alone the week. This may be an extra step not worth taking for some, but we want to make it easier for you to give it a try. 

Below we’ve given a step-by-step guide on outfits that require little effort with pieces like a plant white T-shirt to jeans to ballet flats. We’re steering away from trends to keep these outfits timeless–repeating them is the goal hear. Outfit repeating when your looks is classic is never shameful. We’ve compiled looks that are meant to be worn in comfort in confidence, from any body type too. We’re here to make getting dressed exciting for women of all shapes and sizes rather than anxiety-inducing. 

Keep scrolling to learn more about these timeless outfits that require minimal effort and how to put them together. 

The Formal Outfit 

5 Timeless Outfits For Working Women Of All Ages
NEW YORK, NEW YORK – FEBRUARY 10: Coco Bassey wears a green khaki gathered long dress , a white gathered leather bag, white leather boots, outside Proenza Schouler , during New York Fashion Week, on February 10, 2024 in New York City. (Photo by Edward Berthelot/Getty Images)

A dress is always the easier route when piecing together a formal outfit. We recommend a flowy silhouette for all body types and maximum comfort during the event you’re attending. You could style your dress with a pair of boots and a short heel or with a pointed-toe kitten heel. Try flats as well if you feel you’ll be standing for long periods of time. When selecting a dress, think flattering. Try a dress similar to below with a cinched waist to give you that hourglass shape and fit around your bust. 

The Night Out Look

5 Timeless Outfits For Working Women Of All Ages
NEW YORK, NEW YORK – FEBRUARY 10: A guest wears a black leather jacket, a wool green dress, sunglasses, outside La Pointe , during New York Fashion Week, on February 10, 2024 in New York City. (Photo by Edward Berthelot/Getty Images)

If you’re a working woman or a stay-at-home mom looking forward to or planning a girl’s night out, a leather jacket will always be your friend. A tighter dress is ideal for this look, but for more comfort opt for a looser fit. Over your dress layer a cropped leather jacket in black or dark brown. A pair of black knee-high boots will fuse seamlessly with a look like this. To accessorize, add your own jewelry pieces that make you feel your best like a necklace, a stack of bracelets, a few rings, or large statement earrings. 

The Brunch Look 

5 Timeless Outfits For Working Women Of All Ages
NEW YORK, NEW YORK – FEBRUARY 12: A guest wears sunglasses, a golden necklace, blue and neon yellow sweater, a gray long cotton coat, a black leather Prada rectangular bag, blue denim jeans pants , yellow pointed leather shoes, outside Coach, during New York Fashion Week, on February 12, 2024 in New York City. (Photo by Edward Berthelot/Getty Images)

Brunch with the girls is always a weekly or monthly highlight. If you’ve been dying to try a chic look but need some direction we’re here for you. For those of you who lean on wearing T-shirts and jeans regularly, this look can become your go-to. A white T-shirt with a V-neck or rounded neck will suffice as your base. Add a pair of your favorite jeans whether they’re wide-legged, skinny, or high-waisted. A pop of color is needed: add a pair of pointed toe flats in neon yellow, hot pink, a vibrant blue, or a fiery red. If the weather permits a trench or light wool coat over your outfit will speak volumes to your ability to switch up your style when the moment beckons. To complete your look, a black structured square-shaped handbag is also necessary. 

The Saturday Errand Outfit

5 Timeless Outfits For Working Women Of All Ages
PARIS, FRANCE – MARCH 07: Carrole Sagba @linaose wears a white quilted / padded long shirt from H&M, a brown monogram Fendi bag, blue jeans from Levi’s, Balenciaga black shiny crocodile pattern high heels boots, on March 07, 2021 in Paris, France. (Photo by Edward Berthelot/Getty Images)

When you’re finally at the end of the week, but still have so much to do from grocery shopping to getting new clothes for your ever-growing children, getting dressed becomes a hassle. Being put together will at least have you feeling like a main character while at the grocery store. An easy top is the first step, a white oversized button-down is your best friend for this type of outfit. Next, a pair of well-fitting and comfortable jeans. If you’re able to throw on heeled boots for the day without your feet hurting, then a pair of black block heel boots will elevate your look. Another shoe option is a pair of sneakers like a pair of New Balances. If you won’t need to carry much throughout the day a mini handbag to complete your look would be ideal, but you can also opt for a larger shoulder bag. Finish your look with a pair of gold or silver hoops and be on your way! 

The Cool Mom On-The-Go

5 Timeless Outfits For Working Women Of All Ages
PARIS, FRANCE – OCTOBER 02: Tamu McPherson wears sunglasses, a bi-color dark blue and pale blue denim jacket, a white t-shirt, a blue slit denim skirt, a bag, black leather ankle boots, outside Stella McCartney, during the Womenswear Spring/Summer 2024 as part of Paris Fashion Week on October 02, 2023 in Paris, France. (Photo by Edward Berthelot/Getty Images)

Dropping off cupcakes to school will in this look will have you turning heads. A Canadian tuxedo will never steer you in the wrong direction. Try a denim skirt that isn’t too long with a denim jacket in the same hue of blue or opt for a mixed-blue combo to add more dimension to your outfit. Underneath your jacket layer a plain white T-shirt or tank top, whatever you’re comfortable with. For shoes, black boots with a short heel or a platform heel pair well with this outfit. Add a pair of gold hoops and sunglasses you can sport as you drive away from dropping the kids off to school or daycare. 

From the office to the grocery store, your outfits can be simple, but put together and elevated. Taking the time to plan a look will have you dressing the way you want to and can build confidence to try outfits outside of your comfort zone if you’re open to it. These looks serve as a baseline for getting dressed on a day-to-day as many women including myself are always on-the-go. 



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