Ask CF: How Can I Dress More Maturely Without Looking Boring?

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Looking more mature doesn’t mean looking dull.

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Welcome to the latest edition of Ask CF! Every two weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!

Ask CF Question

Hi CollegeFashion!

I’m in my last year of college, and as my more “adult” style becomes solidified, I’ve noticed that my outfits have gotten more..boring. I consider my style to be retro modern, meaning that I love pieces that are reminiscent of the 1940s, 50s, and 60s, but I keep it modern, like rocking high waisted shorts, Keds, skater skirts, and crop tops, so you get the feel of past decades, but it’s not too costumey.

However, I feel like now, my style doesn’t really have “style” anymore. It just seems to me that my outfits are more or less thrown on or thrown together, like a printed shirt with shorts, without any personal touches. I don’t know how to incorporate my new “adult” clothing (almost every new shirt I have is from JCP’s petite women’s section) into my wardrobe, and have it be young, fashionable, and personal. Is there any way you can help me?
Thanks!

– A Modern Woman in Retro Style

Our Response

Dear Modern Woman in Retro Style,

I think it’s great that you’ve recognized that your style should evolve as you do — it’s something that a lot of people struggle with, so you should be happy that you recognized the issue and can work on it.

Having said that, growing into a new style can be downright confusing, since you’re essentially “re-branding” yourself on the outside.  

Here are a few tips to keep in mind as you move through the process of figuring out your new style: 

  • Don’t be afraid to experiment with jewelry and accessories:  This is one of the easiest, yet somehow the most underrated, way to jazz up your outfits to make them feel more like an expression of who you are.
  • Mix new pieces with older ones: This is a great way to combine your past and current styles, without having to sacrifice one for the other.
  • Stay true to yourself: Dressing more maturely does not mean abandoning what you like; you can still dress in vintage-inspired pieces, for example, but maybe now you may want to combine them with more classic pieces, rather than going head-to-toe retro.

Now, keep scrolling to see the outfits that I have put together for you; note that each one features a top from JC Penney’s petites section, since I noticed that that’s where you said you got most of your new tops from.

Outfit #1

Products: Blouse – JC Penney, Shorts – Mango, Bangle – Nordstrom Rack, Sunglasses – Nordstrom Rack, Wedges – Nordstrom, Earrings – Macy’s, Cross-Body Bag – JC Penney

This outfit is the perfect example of how dressing more maturely doesn’t have to be boring.  Between its fun, vintage-inspired accessories and pops of color, this classy outfit is sure to turn heads!

Start off by tucking a brightly colored blouse into a pair of drapey high-waisted shorts.  

As for accessories, choose vintage-inspired pieces–like this hot pink embellished resin bangle, retro-looking drop-hoop earrings, and a classic pair of cat-eye sunglasses — to make the outfit stand out.  

Next, tie on some espadrille wedges in a neutral color, so as not to distract from the rest of the look.

Finally, grab a pretty pale-blue satchel bag, and you’re good to go!

Outfit #2

Products: Blouse – JC Penney, Belt – Target, Bag – Nordstrom, Skirt – Hollister, Earrings – BaubleBar, Bracelet – Nordstrom Rack, Flats – Target

If you’re looking for something that’s a little more dressed up, try a skater skirt! You mentioned that you like wearing them in your letter, and I believe they are one of the most versatile pieces that you can own, regardless of your style.

I decided to pair this navy blue one with a bright pink ruffled blouse for a look that is at once sophisticated and youthful.

The leopard-patterned belt and gorgeous pearl cuff bracelet add a modern twist to classic motifs, while a boho chain strap bag and cute tie-up ballet flats keep things feminine and light-hearted.

For the final touch, put on a pair of drop earrings, like these statement-making ones from BaubleBar. 

Outfit #3

Products: T-Shirt – JC Penney, Sneakers – Zappos, Shorts – Unique Vintage, Earrings – Revolve, Necklace – Nordstrom, Bracelet – Nordstrom, Sunglasses – Zappos, Tote – J.Crew

This casual and cute outfit was inspired by the 1950s and 1960s.

To get the look, put on a simple gray t-shirt, and tuck it into a pair of ’50s-inspired high-waisted shorts; I love the belt detail on these ones!  

Next, put on a classic pair of Keds sneakers, which add to the laid-back vibe that this outfit has going on. 

Accessorize by adding a pair of ’60s-inspired round sunglasses and a cheerful yellow woven tote.

As for jewelry, choose pieces that are feminine and classic, such as some sweet crystal-and-pearl earrings, a lovely heart necklace, and a chic cuff bracelet.

Outfit #4

Products: Skirt – Unique Vintage, Blouse – JC Penney, Wedges – 6PM, Earrings – Saks, Bangle – Macy’s, Lipstick – Sephora, Cross-Body Bag – Mango

I’ve saved the most glamorous look for last! This outfit is perfect for going out to a nice restaurant for dinner, and would make a great date look as well. It could even be worn during the day, if you’re feeling fancy; just swap the wedges for flat sandals and maybe ditch the lipstick and/or jewelry for a more casual look.

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Begin by pairing an adorable ’50s-inspired gingham midi skirt with a sophisticated pale blue sleeveless blouse.  

Next, tie up a pair of cute gladiator wedge sandals, and pick up a simple beige cross-body bag.

Put on a fun peacock-patterned bangle and some retro-inspired flower earrings.

Lastly, swipe on some bright red lipstick; this one, by Besamé Cosmetics, was inspired by one from the late 1950s. And there you have it–a lighthearted yet mature look that is as versatile as it is pretty!

Have fun experimenting with your new style! Thanks for your question! 

Do you have a fashion question? Send it to us!

Is there something in your closet that you want to wear but have no idea how to style? Do you need advice on what to wear to an upcoming event? Do you have a specific fashion conundrum? If you have a fashion-related question that you would like to see answered in this column, simply email it to askcf @ collegefashion.net, and one day you might see your question answered right here on the site!

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What do you think?

How has your style evolved over the years?  Do you dress differently now than you did a couple of years ago?  How do you keep your style fresh and fun while still maintaining a sophisticated aesthetic?  Let me know in the comments!

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