I’m Struggling with Getting Dressed Lately… Here’s How I’m Fixing It | Jo-Lynne Shane

1. Create Reliable Denim + Shoe Combos

Michael Stars Nara Mock Neck Top (M) // FRAME Lax Flares (30) // Veronica Beard Kelby (8.5) // FRAME Twist Buckle Belt (M) // Jenny Bird hoops

For starters, I realized I don’t have enough reliable denim-and-shoe pairings. I wear jeans almost every day, and when the proportions or hems don’t work with the shoes in my closet, it limits how many outfits I can put together—and the process becomes frustrating.

Right now, a lot of my jeans are too long for the shoes in my closet. I either need to have the jeans altered or buy shoes with higher heels. I’ve been trying to avoid tailoring, so I ordered a few pairs of boots with higher heels, but that led me to my next realization…

Lesson: Every workable wardrobe needs a good variety of reliable denim-and-shoe combinations.

2. Align My Wardrobe with My Real Life

London Fog raincoat (S) // EVEREVE sweater vest (M) // PAIGE Anessa jeans (29) // Jeffrey Campbell flats (8.5) // Mulberry Amberley // Jenny Bird hoops // Baublebar necklace

My life is very casual these days, so when I’m getting dressed for my everyday, I’m almost always reaching for flats or sneakers. Even most of my boots have lower heels because that’s what’s available right now, and it’s what makes the most sense for my lifestyle.

Buying higher heels to make my longer jeans work didn’t solve the problem; it just made getting dressed even more frustrating. That was when I realized my closet doesn’t accurately reflect my current lifestyle. I’m always encouraging others to build wardrobes that fit their real, everyday lives, but in my case, I’d been buying too many pieces that don’t make sense for mine right now.

I have lots of cute going-out tops and longer jeans meant for heeled shoes, but the truth is, I don’t dress up much these days—and lower heels are trending anyway. So the day before I left on this trip, I grabbed a couple of those too-long jeans and took them to Nordstrom to have them shortened. It’s a pain, yes, and I hate waiting to get them back, but I wasn’t able to wear them anyway. Once they’re the right length for my everyday shoes, getting dressed will feel so much easier.

Lesson: The best wardrobes reflect the life you’re living right now—not the one you used to have (or the one you wish you had).

3. Add Everyday Tops That Work for Real Life

VEJA Esplar (39) // AG Mari (30) // Taylor Sweatshirt (last year) // similar camera bag

This ties right into the last point, but it’s another piece of the puzzle as I work toward a more functional fall wardrobe. Once I started paying attention, I realized it wasn’t just my jeans and shoes that were out of sync—there were other gaps too.

I mentioned above that I have a good assortment of “going-out” tops but very few everyday tops I actually want to wear while working from home or running errands. Maybe for you it’s something else—work pants, sweaters, or outer layers—but the idea is the same. We tend to focus on the fun, statement pieces and forget to replenish the simple ones that make our wardrobes truly wearable.

My graphic tees from summer aren’t cutting it now that the weather’s cooler, and I’ve realized I’m missing those “beyond basic” sweatshirts or elevated casual tops—the kind that feel more relaxed than a sweater but still pulled-together. In past seasons, I’ve had some great ones but passed them along (occupational hazard!).

So when I went to the mall to drop off my jeans at Nordstrom for hemming, I also stopped into Evereve—the best place I’ve found for the kind of casual tops I have in mind. I found a couple of good ones… more coming in tomorrow’s try-on haul!

Lesson: Don’t overlook the pieces you reach for most—they’re what make your wardrobe truly wearable.

4. Find the Right Tops to Wear Under Jackets

EVEREVE Bobbie Jacket (S) // LNA Harrison Tee (M) // MOTHER Hustler Roller Sneak (30) // Sam Edelman Saige (8.5)

I love to wear casual, lightweight jackets in the fall, and I’ve found a couple of good ones, but this year I’ve been struggling to find the right tops to wear underneath. What’s trending right now are fitted, cropped tees and bodysuits meant to tuck into high-rise jeans to create those sleek, smooth lines—but that silhouette doesn’t work particularly well for my proportions. And to be honest, those styles don’t feel great when I’m already feeling a little self-conscious about the extra fluff around my midsection. I prefer not to draw attention there—especially if there’s a chance I’ll take the jacket off.

To try and solve this, I ordered this ribbed tee to go with the Bobbie Jacket I’m wearing above (and the Avery Barn Jacket), but I don’t love it for times when I plan to take the jacket off. It’s a great tee—soft, good quality, and well-made—but it’s also quite form-fitting, which doesn’t do me any favors. So I’m keeping an eye out for tops that are shorter and cut closer to the body without being super tight or cropped.

It’s a tricky balance, because the key to layering under jackets is finding something thin enough not to add bulk but still flattering on its own. That’s what I’m looking for—tops that work with my jackets, not just under them.

Lesson: The right layering pieces make your favorite statement jackets more wearable—and they should look good on their own, too.

5. Focus on Fit

Z Supply Stella Henley (M) //  PAIGE Anessa 31″ (29) // adidas SL 72 (8)

Speaking of fit… to be completely transparent, I’ve put on a few pounds since my trip, and some of my favorite jeans just aren’t comfortable right now. Plus, I’m self-conscious about the tighter-fitting tops that seem to be the current look, as mentioned above. This makes it harder to find pieces that feel current and work for my body right now.

It’s frustrating when current trends don’t work for my body or lifestyle, especially with the job I do, but I’m sure many of you can relate. Instead of opting out entirely, I’m trying to find pieces with a similar look that feel better for me—more forgiving but still modern. I know they’re out there; it’ll just take a little extra effort to track them down.

Lesson: You don’t have to follow every trend to the letter; the best pieces are often the ones that interpret it in a way that works for you.

I may also need to size up in a few pairs of jeans, but for now, I’m giving myself some grace and will reassess in a couple of weeks. I’ve put the tighter jeans in the back of my closet and am focusing on styling what fits. (It’ll be easier when I get those shortened jeans back!) Once I feel more like myself again, whether that means tweaking my routine or just adjusting my mindset, I’ll reassess.

Lesson: A great outfit starts with clothes that fit your body today—not last year’s version of it.

Final Thoughts

Every season comes with its own challenges, and sometimes it just takes a little recalibrating. Once I have a few of these pieces in place, I know I’ll find my groove again.

If you’re struggling to get dressed right now too, you’re not alone. Take a little time to reassess what’s working (and what’s not), fill in a few key gaps, and give yourself some grace along the way.