With the prompt “Cozy October” for our Ageless Style group, I thought it was the perfect way to talk about styling sweatshirts in an upscale way.
Of course, everyone has different versions of upscale so I included a couple of ideas in addition to what the three of us decided to wear.

Quote of the day: “Imperfection is beauty, madness is genius and it’s better to be absolutely ridiculous than absolutely boring.” Marilyn Monroe

Insider tip: One of the biggest tips for styling anything is to forget about the category of the item. For instance, think of your sweatshirt as a sweater. Don’t obsess over the material and what it was described as when you bought it.

While it used to be that sweatshirts were only worn for athletic events and working out, times have changed. Yet there is no shortage of ways to style sweatshirts and still look fabulously chic.

This isn’t the first time we’ve had fun styling sweatshirts.

• 3 ways of styling sweatshirts
• 5 unique sweatshirt outfits
• How to style a graphic sweatshirt

1. Pair It with Tailored Pieces: Lesley

One of the most effective ways to elevate a sweatshirt is by pairing it with tailored, structured items. Think of it as a contrast between casual and preppy, which creates an interesting and chic combination.

Lesley did this by wearing her sweatshirt over a collared blouse as well as wearing it with a straight skirt (which is actually a skort, but nobody knows this).

Here are other ideas:

• Blazers: A well-tailored blazer instantly makes a sweatshirt look more polished. Throw a blazer over a neutral sweatshirt, and you have an outfit that’s perfect for a business casual environment or a dinner out. I think both a fitted blazer or even an oversized blazer would be a fun look.
• Trousers: Swap out your jeans or leggings for tailored trousers to give your sweatshirt a refined edge. High-waisted trousers, especially in fabrics like wool or crepe, elevate your outfit and make it look purposeful. Another cool option would be to wear faux leather trousers. I’d call that edgy with a casual flair.

2. Add Statement Accessories: Charlotte

Accessories are the secret weapon for styling sweatshirts into something stylish and upscale. And we know that Charlotte is the queen of accessories.

On top of that, my mom wore her sweatshirt over a dress. It’s a great way to casualize your dresses or upscale your sweatshirt.
More ideas:

• Statement Necklaces: A bold, eye-catching necklace worn with your sweatshirt adds instant glam. Whether it’s a chunky gold chain or a colorful beaded piece, necklaces add sophistication and draw attention to your face. Layering a few delicate gold chains can also give your look a refined, modern touch without feeling too over-the-top.

Insider tip: Don’t worry if your statement necklace covers any words or graphic print on the sweatshirt. They can overlap.

• Statement Earrings: Your earrings can be a magical element to bring the focus to your face. Make sure they show up against your hair and have fun with them. My mom is wearing a shoulder-scraping pair that is colorful and eye-catching.
• Silk Scarves: One of my favorite tricks is adding a silk scarf. A beautifully patterned scarf tucked into the neckline of a crewneck sweatshirt or tied around your neck gives your outfit a polished, European-inspired feel.

Insider tip: Think of your scarf as an alternative for a collared shirt for part of styling sweatshirts. You won’t have the bulk of a shirt underneath the sweatshirt, yet you still have the aesthetics at the neckline.

• Bags: The right handbag can elevate even the simplest sweatshirt. Purses and totes can give an entirely different vibe to a look. For example, my mom added this owl tote bag for a whimsical vibe.
• Footwear: We all know that shoes can make or break a look. It’s very modern to wear ankle booties or sneakers with dresses instead of just heels or flats.

3. Mix Textures for Depth and Interest: Jodie

Another way for styling sweatshirts in an upscale way is to mix in luxurious textures. Pairing your casual sweatshirt with rich fabrics like satin, silk, leather, or velvet creates a fashion-forward look that feels anything but basic.

Insider detail: You may be saying, “But Jodie, you’re not wearing a sweatshirt.” I took a sweatshirt (details below) and made a skirt out of it. So yes I am.

• Leather Pants or Skirts: Leather always adds a touch of sophistication. Pair your sweatshirt with leather pants for a sleek, edgy feel, or try a leather skirt for a feminine yet modern vibe.
• Satin or Silk: Satin and silk have a natural sheen that elevates your outfit, giving it a luxe feel and adding a layer of dichotomy compared to the casual vibe of sweatshirt material. My satin blouse creates this fun yin/yang.
• Velvet: For colder months, adding velvet to your outfit is a great way to elevate a sweatshirt. Velvet is one of those materials that seem dressy and thus gives that opposite feeling of the sweatshirt.

Insider tip: I added a pin to the waistband to try to hide the tie.

4. Experiment with Layering

Layering is another great way to elevate a sweatshirt. When done right, layers add dimension to your outfit and make even the simplest sweatshirt look intentional.

• Collared Shirt Under a Sweatshirt: Layering a crisp collared shirt under a sweatshirt is a classic styling trick that instantly elevates your look. Let the collar and cuffs peek out from underneath for a preppy yet modern twist. This is exactly what Lesley showcased.
• Layer with a Long Coat or Duster: A long coat or duster cardigan adds elegance and movement to your outfit. Wear your sweatshirt with fitted pants or a midi skirt, and throw on a floor-length coat or cardigan to create a dramatic, upscale vibe.
• Vest or Cropped Jacket: For a trendier look, try layering a vest or cropped jacket over your sweatshirt. This adds depth and visual interest while keeping you warm and stylish.

Insider tip: While most of us think of sweatshirts as baggy and nonstructured, it’s nice to have more fitted ones in your arsenal which will also allow you to layer over them.
Don’t forget to check the secondhand stores for these items.

5. Tuck or Cinch Your Sweatshirt

Sometimes, it’s the little styling tricks that make the biggest difference. Tucking your sweatshirt or cinching it at the waist with a belt can create a more polished silhouette, especially if you’re wearing a looser or oversized fit.

• Half-Tuck: For a laid-back yet elevated look, try a half-tuck—tucking the front of your sweatshirt into your waistband while leaving the back loose. This gives your outfit some structure and shows off your waistline, making the look feel more intentional.

Insider tip: If there’s too much bulk for tucking, try using a hair elastic to pull in the material and then you can tuck that tail under the sweatshirt.

• Belted Sweatshirt: If your sweatshirt is slightly oversized, try cinching it at the waist with a stylish belt. Whether you use a slim leather belt or a wide statement belt, this trick helps define your shape and adds a layer of sophistication to the outfit.

Insider tip: Sometimes using a long scarf works fabulously as a belt for styling sweatshirts.

DIY a Sweatshirt to a Skirt

This is a super duper easy DIY that you can do with no sewing skills and no sewing machine.

Insider tip: The bottom ribbing is going to be the waistband, so that’s how you will check for sizing. It will be finished off with a tie, but you don’t want the waist too big because then you get too much gathering.

#1– Cut your sweatshirt right under the armhole to make it as long as possible. Of course, you can cut it shorter if you want.

#2– Take the lower portion and turn it upside down so the ribbing will become your waistband. Cut off a half-inch of the sweatshirt to become the ties.
Take this half-inch of material and stretch it to be used as the waistband tie.

Insider tip: I cut the extra sweatshirt for the ties from the top portion so my skirt would be as long as possible.

#3– Take sharp scissors and snip 2 holes in the waistband through the top layer only.

#4-Place a safety pin on one end of the tie and wiggle it through the ribbing to end up at the other cut area.

#5– Make a bow at the waist and wear it with pride.

Insider tip: Don’t throw out the top part of the sweatshirt. You can wear it as a cropped covering (basically like this one only a bit longer).
You might ask how it will keep you warm. It’s basically coverings for your arms that can be helpful during workouts when you don’t want a lot of material.

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Ageless Style

Welcome to the Ageless Style group. We all have very different styles, so I hope you check out other ideas for a cozy October.
We don’t all post at the same time, so make sure to check back if their post isn’t up yet.

Next month we are styling chocolate brown and cream if anyone wants to join in.

Amy ~ Amy’s Creative Pursuits
Blog | Instagram | Pinterest | Facebook |
Bo ~ Bo’s Bodacious Blog
Blog / Instagram /Pinterest / Bloglovin’
Jennifer ~ Overflowing With Thankfulness
Blog | Instagram
Joanne ~ My Slice of Life
Blog
Jodie ~ Jodie’s Touch of Style
Blog | Instagram | Facebook |
Leslie ~ Once Upon a Time and Happily Ever After
Blog | Instagram | Pinterest | Facebook |
Marsha~ Marsha in the Middle
Blog /Instagram
Mireille ~ Chez Mireille Fashion Travel Mom
Blog | Instagram | Pinterest | Facebook |

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Photo credit: Rob Filogomo

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Welcome to Jodie’s Touch of Style. I’m here to prove that it’s never too late to look great. Clothing and style are meant to showcase your inner personality. So let’s have fun and try new things.

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The post Styling Sweatshirts In An Upscale Way appeared first on Jodie’s Touch of Style.

Jodie Filogomo Fashion Stylist

Jodie's Touch of Style showcases how it's never too late to look great including other older women and myself talking about fashion, beauty, and lifestyle issues.

As a retired dentist, Jodie takes her love of clothing and shopping and has come to find her superpowers in styling the same item in many ways. She is also a huge advocate for embracing our age and bodies. Getting old is a wonderful thing and learning to love ourselves while it happens is very freeing.

Looking great can happen no matter what age, shape or budget, as we show on Jodie's Touch of Style.