One of my favorite things about fashion is that one person can style a certain piece of clothing one way and another might style it completely different. You know what you enjoy wearing, whether it’s certain colors, textures or even specific retailers you gravitate towards. However, some things are harder to style than others, depending on what your own personal style is. I’ve been there, and get it! So today, I’m talking about overcoming your biggest style challenges.

Recently, I asked on Instagram if there was anything specific that you’re not as confident styling. And boy, did I get a lot more responses than I was anticipating! I’m sharing a few responses that I received and talking through different ways to style these pieces.

For more how-to-style posts, you’ll love these HERE.

Overcoming Your Biggest Style Challenges

Style Challenge #1: Jumpsuits

overcoming your biggest style challenges

The first style challenge is about how to style jumpsuits. The submission made me laugh because it said “Jumpsuits. Want to love them, can’t help but feel like an oversize toddler!” I can totally relate to this.

My suggestion is to style them with a heel. It doesn’t have to be high. But giving yourself a lift like that will give a more feminine look and help lengthen your legs.

You also want to highlight what your confident in showing off. Whether it’s an open-back silhouette, a plunging neckline or a sleeveless option, this will help you look less toddler-like. 🙂

Finally, you’ll want to avoid patterns. A solid color looks a bit more streamlined and elevates the overall look without it looking too busy. You can definitely wear a fun color – just avoid too much pattern if you’re wanting to look to be more sophisticated.

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Style Challenge #2: Denim Shorts

overcoming your biggest style challenges

A couple years ago, I could have related to this one as well. I wasn’t in love with denim shorts then. In high school and throughout college, I remember purchasing multiple different denim shorts. But found them to be either too snug in the legs, rolled weird, and just weren’t doing my body justice. That is until I discovered an Agolde pair of denim shorts in 2019. That changed the game for me when it came to denim shorts, and haven’t purchased any other brand since. These are my favorite pair, and wear a size 28.

When it comes to styling denim shorts, pairing them with basic tees and then adding fun accessories is an easy way to style them. Pair them with white sneakers, sandals, or other casual shoes.

If you want to dress them up, you can style them with blazers. Keep in mind the length of the blazer. You don’t want the jacket to be longer than the shorts and make it look like you’re not wearing pants from the back. I 10/10 don’t recommend that.

When the weather is transitioning from summer to fall, you can also pair them with an oversized sweater and do a front tuck. It keeps the shape of the overall look. I also like to layer kimonos over a tank or tee throughout the summer and fall.

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Style Challenge #3: Form-Fitting Dresses

overcoming your biggest style challenges

With form-fitting dresses, a darker shade is more flattering to wear than a lighter shade because dark colors hide areas you don’t want to highlight. If you don’t like wearing black, dark chocolate or wine color would be pretty and flattering, too. The type of material also makes a difference in form-fitting dresses. Finding something thicker will hold you in a bit more, and ruching is also another flatting detail to look for!

You also have to know your body shape a little better to feel more confident as well. For me, I have a shorter waist. So I know what to look for to best dress my body type.

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Style Challenge #4: Dresses with Booties

overcoming your biggest style challenges

When it comes to shorter dresses, I like to style short ankle booties with them versus a bootie that goes up the leg a bit more. I especially like to wear a bootie style with a cutout on the side to add length to the bottom.

If I do wear a bootie that goes past the ankle, I try to stick to lighter-colored booties that are similar to the color of my skin. That way I don’t have that stark contrast between the color of the boot and my skin color because depending on your body shape, that can easily make you look much shorter. In the above example, I’m wearing a bootie with a higher shaft and it doesn’t cut me off since it’s in a lighter color and the dress his well above my knee.

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Style Challenge #5: White Jeans

With white jeans, I think it comes down to the type of jean or pant you wear. You want to stay away from pants that show the pocket, are too sheer or look bunched up in certain places, those are really going to be accentuated with white jeans.

However, if you get a pair that fit well and are good quality, I think they’re one of the most versatile pieces you can have in your wardrobe. I wear mine year round because white is a neutral color. The Spanx white jeans are one of my favorite pairs and can use my code: AMANDAJOHNxSPANX for 10 percent off your purchase.

When in doubt, I suggest trying the next size up in white pants. I find they can look more flattering with a little extra room!

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Style Challenge #6: Bodysuits

overcoming your biggest style challenges

I wear bodysuits all the time as a layering basic. For some people, I think the idea of having to snap a bodysuit really turns them off. But I never snap mine, and just tuck the two pieces where they’re supposed to go. Bodysuits are great to wear with more form-fitting bottoms because they provide a seamless look, like skirts or jeans. They’re my to-go when pairing something looser on the bottom to balance out the look.

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Style Challenge #7: Western Booties

I bought a Western bootie in the Nordstrom Anniversary Sale this year. If you want to do something a little more sophisticated, I would do a fitted monochromatic look or pair them with something unexpected like a blazer.

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Style Challenge #8: Straight Jeans

I know many of you are Millenials, like myself, and struggle with letting go of the skinny jean game. I still wear skinny jeans because you should wear what you feel comfortable in. However, I have incorporated straight jean styles into different looks as well.

I tried on so many pairs of straight-leg jeans until I found two I felt confident in. So don’t give up if your first try is a fail! You can also try finding more of a slim straight style to ease you into the transition. I wear a 27 in the Madewell straight jean, which is a size down from my normal style.

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Style Challenge #9: Faux Leather Leggings

If you’re coming for style inspo on faux leather leggings, you’ve home to the right place. Here’s a blog post sharing different ways to style them. Also, there are different styled options throughout my LTK account. If you search faux leather leggings in LTK under my account, there’s plenty of different options on how to style faux leather leggings there too! My favorite pair are definitely the Spanx faux leather leggings. I wear a medium in them. Use AMANDAJOHNxSPANX for 10 percent off your purchase.

My go-to look for faux leather leggings is a knee-high boot with an oversized sweater. It’s basic, but it’s comfortable and cute!

Style Challenge #10: Athleisure Favorites in Public


A jogger is a great alternative to leggings, if you don’t enjoy wearing leggings in public. I’ll sometimes wear my Ultra-Boost sneakers, joggers, a bodysuit and a denim jacket for a put-together, yet comfortable look. That also makes a great travel outfit.

Another athleisure piece that I love is the cozy wrap jacket from Zella. You can wear it open or closed, and made of sweatshirt material but looks more chic than an oversized sweatshirt.

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Style Challenge #11: Off-the-Shoulder Tops

This submission was talking about how they have broad shoulders, and I totally relate! This is something I don’t wear often because I don’t think it flatters my body type.

I would try a one-shoulder top, so you’re giving it a different shape than a straight line across or look for something off the shoulder that has an angled cut to it to avoid cutting you straight across.

Style Challenge #12: Silk Neck Scarves

I just purchased this Dior scarf and after only having it a week I’m finding it very versatile in my wardrobe. A new chic way I’ve worn it is around my wrist like a bracelet. You can also tie it in a knot around your neck, on your handbag, or even just draped around your neck under a collared top or blazer.

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Do you have a style challenge? Let me know in the comments below!

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