Help Me Style This: Checked Pants Edition

Introducing a New Series: Help Me Style This

We all have that one piece in our closet that we love but can’t quite figure out how to wear. Maybe it’s a bold pattern, a tricky color, or something that just never seems to go with anything. Enter my new illustrated series: Help Me Style This.

Each post in this series will feature a “problem item” — either sent in by a reader or suggested by a friend — and I’ll create a series of illustrated looks to show different ways to style it. The goal? To spark ideas, boost confidence, and help you see your wardrobe with fresh eyes.

This Month’s Challenge: Checked Pants

This first edition came from a friend who sent me a photo of her favorite pair of brown checked pants. She loved them but was struggling to make them feel versatile. She asked for ideas that felt casual yet pulled-together — something that worked for errands, coffee dates, and outings.

Using her pants as the base, I built out a full set of outfit ideas that mix textures, colors, and moods. Each one shows how small swaps — a sweatshirt instead of a sweater, or a blazer instead of a vest — can completely change the vibe.

The Pieces

When I’m styling around one item, I like to mix classic staples with a few unexpected choices. The goal is to show how one piece can work with different moods and textures, not to recreate a specific closet. Don’t get me started on the capsule wardrobe (I could do a whole post on this and why I don’t love them!). While it’s a great start, I’m a firm believer that you need to have some fun and personality with your clothes. You don’t need all basics or all one of a kind pieces, you need a mix. Here’s what I pulled together for this set:

• Denim Vest A denim vest instantly adds structure and texture without feeling too formal. It bridges the gap between seasons and layers beautifully over shirts or knits.
  Swap idea: A chambray or denim shirt would give a similar look — soft, casual, and classic.

• Logo Sweatshirt A playful sweatshirt (mine reads “San Francisco 1994”) balances the tailored feel of checked pants with something laid-back. It’s the ultimate high-low combo.
  Swap idea: Any sporty sweatshirt works here — think your favorite college crewneck or vintage team logo.

• Oversized Blazer A wardrobe MVP. The oversized blazer gives polish without being stuffy, grounding patterned pants with clean lines.
  Swap idea: Try a cardigan or even a longline knit blazer for the same layered structure but a cozier feel.

• Classic White Button-Down Crisp, timeless, and endlessly versatile — it’s the perfect balance for bold pants. Tuck it in, layer it under sweaters, or wear it open with a tee underneath.
  Swap idea: A tuxedo-style shirt or one with interesting detailing (ruffles, pintucks) adds subtle personality.

• Fuzzy Olive Sweater Texture makes an outfit interesting, and this soft olive green knit does exactly that. It adds warmth and a nice contrast against the structured pants.
  Swap idea: Any olive, sage, or neutral-toned sweater would work beautifully — or even a cozy cardigan in a similar palette.

• Ruffle-Collared Shirt Feminine, fun, and just a bit unexpected — the ruffle collar peeking out of a sweater or blazer brings a nice mix of polish and playfulness.
  Swap idea: Try a silky blouse in chambray or light blue for a softer, more modern twist.

• Cream V-Neck Rib Knit Sweater This cropped rib knit is the definition of cozy meets chic. It tones down the pattern while keeping things visually balanced.
  Swap idea: A fisherman or chunky knit sweater in cream would also work perfectly — you get that same soft contrast against the checks.

• Graphic Tee A good tee is the secret to making patterned pants feel easy. It adds personality and keeps things from feeling too put-together.
  Swap idea: Any fun or casual tee works — from band tees to quirky sayings to vintage finds.

• Zippered Hoodie Because sometimes you just need comfort. A hoodie brings instant cool and can make even the most tailored pants feel relaxed and lived-in.
  Swap idea: Any hooded top or casual pullover (think quarter-zip or funnel neck) gives that same off-duty vibe.

Style Takeway: It’s not about having these exact pieces — it’s about using what you already own (or can easily find) to create contrast, texture, and balance. The magic happens when you mix something structured with something relaxed, or dressy with casual. That’s how one tricky item becomes infinitely wearable.

How I Styled Them

Cozy & Neutral A cream ribbed sweater paired with the checked pants keeps things soft and cozy. The neutral tones balance the bold pattern, creating an effortless everyday look that still feels polished. Add sneakers or loafers and you’re set for a casual brunch or WFH day.

Classic Button-Down Remix A crisp white shirt is always a win. I layered it under a denim vest for a modern twist — it adds structure without feeling too formal. You could also swap in a chunky cardigan or cropped sweater for texture.

Unexpected Pairings A ruffled blue blouse and the checked pants? Yes, please. It’s feminine meets vintage, especially layered with a neutral knit over top. Playful yet elevated — perfect for a lunch date or creative office day.

Sporty Layers A grey sweatshirt or hoodie instantly dresses the pants down, but pairing it with a tailored blazer brings it right back up again. It’s that “I just threw this on but look amazing” energy. Think: travel days, school pickup, or laid-back Friday at the office.

Pops of Personality A peach tee or graphic top adds a little brightness and humor — I especially love the contrast against the earthy checks. Toss a blazer or olive knit around your shoulders for a casual, intentional finish.

Texture Play Corduroy, wool, and knits all pair beautifully with check prints. A wool blazer or a soft, oversized green sweater gives dimension and keeps the look grounded in fall tones.

By mixing silhouettes, colors, and fabrics, I created a slew of looks — all centered around one pair of pants. It’s proof that a “problem piece” just needs the right supporting cast to shine. There are so many more possibilities with these pants. All of these looks steer casual, but I could have made them more dressy, sporty, or edgy based on the pieces I selected. And let’s not forget shoes and accessories. Those can also change the vibe completely. It all comes down to personal style and wearing what makes you feel like you.

Want to Get Involved?

Do you have something in your closet you can’t quite figure out how to style? Send it my way! Each month I’ll feature a new reader submission as part of Help Me Style This.

You can submit a photo or description of your item, and I’ll create illustrated outfit ideas to inspire new ways to wear it.
👉 Email me at erin@denimandink.com or DM @denimandink to take part.

What’s Next

I’ll be sharing a new Help Me Style This post each month — from statement skirts to tricky jackets and everything in between. Whether you’re looking for outfit inspiration or just love seeing how pieces come together visually, I hope this series gives you ideas to make your wardrobe more fun, flexible, and uniquely you.