45+ Affordable Workwear Outfits

I am back again this week for part two of our workwear series! When I started styling these looks I was so inspired that I blew right past 30 outfits and curated an additional 19 looks for you. In today’s post, I’m bringing you 45+ affordable workwear outfits! Each of these looks feature pieces that are less than $150 and can easily be styled multiple ways.

I had so much fun putting these together for you. This collection of workwear looks is styled with teachers and a business casual office setting in mind. Be sure to take inventory of your closet. Assess the pieces that you’ve already invested in to see how you can use those to recreate these looks!

In case you missed it, check out last week’s post with over 30 teacher workwear looks for back to school!

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We are kicking things off with a classic tweed skirt from LOFT. This shift style skirt hits mid thigh and is perfect for transitioning from summer to fall. I styled it three ways. First, I paired it with a classic white button down and tan loafers. Next, I paired it with a crew neck sweater and my favorite Sam Edelman Hazel heels. I also styled it more casually with a denim shirt tucked in and a cozy cardigan from Target. To see this cardigan styled multiple ways, check out THIS reel!

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If you’re on the hunt for a sweater that can go from business casual teacher look to elevated fall look, I’ve got you covered! This oversized dolman sweater is not only comfortable but chic too! It comes in three other colors and fits true to size. Pair it with wide leg pants, like this pair from Spanx, or style them with the same tweed skirt from above.

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If you’re loving the dolman style, but aren’t ready for sweater season just yet, opt for a dolman style sweater vest. I layered this one over a silk slip dress to give the illusion of a skirt. I recommend adding a thin belt to give you a more defined waistline.

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This next look features a neutral peplum sweater tank and classic pointed toe heels. To take this look from summer to fall, simply add a blazer over the top! This is also an easy way to extend your wardrobe from season to season.

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This next look is my go-to for when I’m in need of a chic look, but I’m running short on time. Simply layer a structured blazer over the top of a midi dress and add neutral heels. I’ve had this pair of pointed toe suede pumps from Sam Edelman for years. They have a padded cushion that allows for extra comfort throughout the day.

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Can we give a little extra praise for the sneaker trend? This is one of those fashion trends that also happens to line up with comfort, and I’m here for it. I love to pair a white sneaker with a midi dress for a casual Friday look. If you need an extra layer for warmth, add a denim jacket or lightweight cardigan.

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It’s no secret that I love an animal print dress. This one is an Amazon find that was too cute to pass up. The v-neckline is very flattering and draws your eyes upward. I also love that the length hits a little past mid thigh. I recommend a knee high suede boot or flats for this length dress.

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This next look features a classic high waisted trouser pant and long sleeve ruffle blouse. I love the elastic waistband on these Amazon dress pants. They are a great option if you’re wanting a pant that is comfortable and also professional. The material doesn’t wrinkle, so if you’re traveling or sitting for long periods of time, I recommend wearing these!

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I like to have a little fun with my workwear looks throughout the week. An easy way to do this is incorporate a bold color blazer! When paired with classic black pants like this cropped flare pair from Target, you instantly look put together.

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These Target pants are by far one of my most worn pairs of dress pants. They are a high rise and have just the right amount of stretch. I love that you can style them for a business casual setting or dress them up with heels and a blazer.

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A black pencil skirt is a work wardrobe must have. This one from Banana Republic Factory is a great affordable option. It’s less than $40 and fits true to size. I styled it three ways. The first is with a bright red blouse for a bold look. Then I opted for a floral top and layered a cardigan over the top. Finally, I paired it with leopard print flats and a neutral top. If you’re wanting a more elevated look, swap the flats for heels and add a blazer.

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An easy way to transition your wardrobe into fall is to be mindful about your color pallet. The short sleeves and lightweight cotton material of this button front dress is great for warm weather while the rich golden color screams fall. Another easy way to transition into fall is with light layers. By adding a cream ribbed open front sweater and closed toe shoes, you’ll instantly look like you’re ready for the season ahead.

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A henley top and stripes are a classic combo that never go out of style. This workwear look has a menswear inspired vibe with the high waisted trousers and buckle top loafers. As we move into fall, layer a camel trench coat over the top to complete the look!

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I mentioned in my last teacher workwear post that I believe a denim dress is a closet staple, and I stand by that! You loved the last denim dress I shared, so I thought I would give you a long sleeve option for fall! Style this dress on its own with flats or layer a sweater over the top!

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This dress is the perfect mix of fun and flirty meets professional. The full skirt and ruffle detail give it a youthful element that I love. Pair it with suede knee high boots and stack a few of your favorite bracelets to complete the look.

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A midi skirt is another one of my favorite versatile workwear pieces. I love that you can dress it up with heels and a button down or style it more casually with an oversized sweater and flats. Another option would be to add sneakers!

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I was so excited when I came across this dress. The buttons on the front are functional, making it the perfect workwear option for my nursing mama friends. The bright blue is so pretty and the tie waist silhouette is extremely flattering!

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How fun is this ruffle sleeve dress from J. Crew Factory? The lightweight cotton material is great for transitioning into fall. I styled it two ways, business casual and business professional! The look on the left is perfect for all my teacher friends. The look on the right is great for a business professional setting. By adding a thin black belt, heels and a sweater blazer, it instantly takes this dress from casual to elevated!

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In this next set of outfits, I’m styling the same sweater blazer from above with another dress. This drop waist dress is another piece that can easily be dressed up or down. In the look on the left, I styled it with heels for a business professional look. In the look on the right, I added sneakers for a casual look that can be worn into the office or while running errands on the weekend.

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This marled long sleeve midi dress is another great transitional piece. I love that the neutral color allows you to style it multiple ways. I paired it with sneakers and a backpack for a casual teacher workwear look. To see it styled for a business casual setting, keep scrolling!

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To kick this dress up a notch, add a classic black blazer and a chunky necklace. Since the blazer and dress are both very neutral, I opted for a fun leopard print flat. These are made by Rothy’s and are by far my most comfortable flats that I own. I love that they are machine washable and eco-friendly.

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This v-neck dress is another piece that you can wear now and later! If you’re in a cool classroom or office, bring a black blazer as a layering piece. This allows you to look professional and stay warm. Complete the look with suede pointed toe flats and and a cream tote bag. The tote bag is a Target find. It’s lightweight, has multiple pockets and is only $40!

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You can’t go wrong with a little black dress. I love that the puff sleeve detail and oversized buttons give it a trendier feel. I styled it with leopard flats and a work tote bag for a look that you can wear now. As we move into fall, add an open front cardigan and sneakers!

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In case you’re new around here, floral dresses are a Loverly Grey favorite! My favorite look for fall is pairing knee high suede boots with a dress that hits right above the knee. I picked these boots up during the Nordstrom Anniversary Sale. I love the lower heel height and the light tan color.

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Another signature Loverly Grey look is incorporating layers when wearing a dress. I love to layer sweaters or sweater vests over the top of a floral dress to give the illusion of a skirt. This is a great way to create endless outfit options!

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I love to incorporate faux leather pieces into my work wardrobe. This pocket shift skirt from LOFT is an easy way to bring a more on-trend element while still maintaining a professional feel to your outfit. I opted to style it with a classic white button down and leopard flats.

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Another way to style this faux leather skirt is to pair it with a button down and a sweater. This top is actually one set. However, you can recreate this look using two separate pieces! I also styled it with a printed blouse and flats for a business casual fall look.

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For our final look, I’m styling this zebra midi dress three ways! The first look is perfect for a business professional setting. The trick to layering is a coordinating color palette and creating a defined waist. In this case I used the fabric belt that came with the dress. I curated the second look with a more casual vibe in mind. This is a great option for casual Friday or a more relaxed office dress code. Finally, I kept it simple and classic with pointed toe suede flats with a gold chain detail.

Which of these 45+ affordable workwear looks are your favorite?