My work days are typically spent in workout wear, or if I’m feeling really fancy, jeans and a tee. But I got my first job when I was 15-years-old (Corn Dog on a Stick at the mall food court #holla), and have worked ever since. In fact, there’s never been a time since then that I didn’t have a job!

I’ve done everything from waiting tables at a Mexican food restaurant (obviously) and folding shirts at the Gap, to managing advertising accounts and overseeing the operation of a national magazine.

Basically, I’ve adhered to every possible office dress code at one point or another! So while my daily look is more casual now, I still have a deep love for true ‘office wear’, and in fact, work wear is one of my most-requested styles from you. (See all of my Work Wear posts here.)

But you know I don’t categorize clothes for just one use!! We’ve got to stretch that wardrobe and adapt pieces for both Work and Weekend. Today I’m sharing several styles from Ann Taylor, and all centered around this gorgeous floral blouse. Because it’s just too pretty to not wear seven days a week!

Wide Leg Plaid Pant | Floral Tie Neck Blouse | Suede Pumps | Round Drop Earrings | Similar Sunglasses

The first style is a little bit ‘extra’, but so am I. The mix of floral and plaid is so fun, but since both patterns are classics, it’s totally work-appropriate.

Let’s start with the blouse! It was the first thing I spotted upon walking in the store, and even though I typically don’t do large patterns, I was instantly drawn to it! The colors are perfection for Fall, and it feels so good on. It has pretty feminine details at the shoulder and wrist, and can be tied several ways for different looks.

The pants are wide-legged with a cropped hem, hang beautifully, and have an amazing fit. I love them paired with these sexy pumps, and would wear them with knee boots once it cools off even more. If you prefer a more neutral style, I’d pair the pants with a fitted sweater or solid top.

Fit Tip: I’m wearing an XXS blouse (the small petite fit well, too), and a 2 petite pant. The regular 0 was a good fit, but too long for my 5’4″ frame.

Wide Leg Plaid Pant | Floral Tie Neck Blouse | Round Drop Earrings | Similar Sunglasses

For this style, I tied the blouse in a bow, but pulled my hair back to keep it from being ‘too much’ around my face. I let the blouse make the statement, and kept the rest of my accessories minimal.

Wide Leg Plaid Pant | Floral Tie Neck Blouse | Suede Pumps | Round Drop Earrings | Similar Sunglasses

Next up I paired the blouse with a pencil skirt for a more classic work style. But thanks to the vibrant pattern of the top, it’s anything but boring!

Floral Tie Neck Blouse | Seasonless Stretch Pencil Skirt | Suede Pumps | Round Drop Earrings | Similar Sunglasses | Bag

For a more relaxed look, I simply knotted the tie and let the ends loose. The pencil skirt is a great year-round closet staple, with flattering high-waist fit and just enough stretch.

The suede pumps are comfortable enough for all-day wear, and sassy enough for all your evening looks, as well. They come in several colors of leather if you’re not a suede girl.

Fit Tip: I’m wearing a 2p skirt. The pumps are true to size, as well.

Floral Tie Neck Blouse | Seasonless Stretch Pencil Skirt | Suede Pumps | Round Drop Earrings | Similar Sunglasses | Bag

And finally, let’s take this gorgeous floral on the town! I love it paired with black skinny jeans for a sassy and sophisticated style that’s perfect for after-work drinks, or even casual Friday.

Floral Tie Neck Blouse | Black Stretch Jeans | Suede Sandals (40% off!) | Round Drop Earrings | Similar Sunglasses | Bag

When worn untucked, the blouse hangs like a tunic and doesn’t cling or hug. I left a few buttons open at the neck, and the tie loose.

The jeans are extra-stretchy with a comfortable fit at the waist. This modern fit is leaner through the hips and thighs (almost like a jegging), but they also come in a curvy fit for more room. They are jet black with no distressing, and don’t stretch out or loose their shape during the day!

Fit Tip: I’m wearing a 2p for a cropped length.

The clutch just slips right out of the bag from earlier! And absolutely you can mix black and brown! Just make sure your brown is a lighter shade, like tan, cognac, or taupe.

Floral Tie Neck Blouse | Black Stretch Jeans | Suede Sandals (40% off!) | Round Drop Earrings | Similar Sunglasses | Bag

One of best parts about shopping Ann Taylor (besides their amazing quality and classic styles), is the wide range of sizes available. Most everything comes in regular and petite, and even some talls. I find the sizing comparable to Loft, which is helpful when shopping their extensive online selections.

So what’s your Monday-Friday style? And even more fun, what was your first job?

*Photos by the darling Audrie Dollins. This post created in collaboration with Ann Taylor and ShopStyle, but all styling, opinions, and #girlboss impersonations are my own. Thank you for supporting Hi Sugarplum sponsors!*