How To Wear A Sweatshirt And Not Look Frumpy

Deborah BolandWhat’s the newest way to wear jeans and a top? Try swapping out your tried-and-true t-shirt for something bolder: a sweatshirt!

If this sounds like a fashion nightmare, keep an open mind.  Here are some ideas for how to wear this new look that won’t make you look like a frump.

purple sweatshirt

As you can see ( above) we’re not talking about that ugly varsity number from your college days or some oversized monstrosity with a hood. There’s a new incarnation of the sweatshirt in town, and it’s surprisingly chic.

Fitted but not tight, sans hood, and decked out with every array of embellishment imaginable, these new sweatshirts are surprisingly stylish and wearable!

Popularized by J. Crew and Alexander Wang, sweatshirts with lace, embroidery, sequins, cool graphics and even fabric panels have had their moment. To pull them off in an age-appropriate way, follow these tips:

  • Pick a sweatshirt in a sophisticated shade to avoid looking shlubby. Also, make sure it is fitted and keep the chic embellishments on the sweatshirt itself to 3 or less. Any more will be overkill!


  • Get the Right Fit. The slouchy silhouette flatters most body types but if you are bottom heavy try a looser hem instead of a tight band.


  • Pair the relaxed sweatshirt with something more fitted. Try wearing one of these luxe sweatshirts with skinny jeans or leather leggings for a more casual look, or dress up your sweatshirt with slim-cut pants or even a pencil skirt.


  • Leave the sweatshirt untucked. If you don’t your midsection will look bulky. Also, if you are bottom stay away from a tight band at the bottom and go for a loose hem. You could even try wearing your relaxed wide necked sweatshirt slightly of kilter, to one side, to take the emphasis off the straight line right across your lower tummy.

black sweatshirt


  • Counter the inherent casual nature of a sweatshirt with bold jewelry. A graphic necklace, bold watch or big pair of earrings are the perfect icing on the cake! Keep it to one or two jewels to not overwhelm your look, though.


  • Choose the right footwear. Sweatshirts are sporty but no running shoes please. Ankle booties are the perfect medium between casual and dressy, making them a natural pairing to your sporty-glam sweatshirt! Dressy flats fit the bill, too, if heels aren’t you thing.


  • Finish off your outfit with a statement bag that does not match your shoes! Pick something big and tailored in a complimentary color to your outfit. A great tote works, so does an oversize clutch.


  • Add a dash of lipstick and you’re ready to go! The new sweatshirt is the perfect mix of comfort and glam, a trend that looks great at any age. Step up your style with these tips and try the trend.

Will you be trying the sweatshirt trend? I bought a cashmere sweatshirt  that I wear with black leggings. Take a look.

Guest Contributor Stylist: Morgan Mullin


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  1. Mira Hornbeak says:

    I love the look – I purchased several cute mixed blend fabric sweatshirts from Target or Tajae`!! Being a woman over 40, I thrilled to receive so many compliments, especially when worn with riding pants and boots! Winner!

  2. Lisa Macdonald says:

    I love the white sweatshirt with black design on your website where can I get it! Your website is wonderful just what I was looking for. I AMA nuse and where uniforms daily so when I have to dress up I just don’t know what do wear and jeans and plain tshirts are boring. Thanks

  3. Margaret F says:

    Already got a few from Jones of NY for Spring

  4. Who makes that blue sweatshirt with the black on the top of it in the outfit above? I love it.

  5. Carole Freeman says:

    As someone who is top heavy “apple shaped” would it be ok for someone this shape to wear a sweatshirt without looking big on top. Lolly pop shape!