Casual yet Stylish Back to School Outfit Ideas (Dress for that A Grade)7 min read

Here is styling inspiration on back to school outfits that are sure to get that A-grade.

Summer’s quickly coming to an end and it’ll soon be time for pencils, books and teacher’s dirty looks. You can hear the collective sigh of millions of students across North America.

I remember when I was younger, back to school was a reminder of less late night TV and the dreaded return of daily homework and pop quizzes. It also meant that it was time for a new wardrobe.

Every year I’d drag my parents to go back to take me back to school shopping. They would always take me to Ross because they knew that I could “Dress for Less.” That is the tagline if I’m mistaken?

I never really knew what to wear for the new school year. All I knew was that I wanted to show off all my fresh threads to all the other kids. If you’ve been following Gentleman Within for a while now then you know that I’m starting to lean towards a more casual aesthetic with an emphasis on minimalist style.

I’m of the mindset that it’s better to own less and to make the most of the pieces that you do have. This is also known as a capsule wardrobe.

With this year’s back to school season in full swing, I want to provide some casual men’s outfits and styling inspiration for essential styles you may already have in your closet.

To watch the lookbook, hit the play button in the video below.

CASUAL MEN’S OUTFITS FOR SCHOOL

So let’s dive right in on some men’s back to school outfit ideas that you can experiment with today.

All four of these men’s outfits for school lean casual which is perfect for most students. They’re dressed down looks that will have you looking more stylish than a majority of your peers, so take notes!

Oh, and for reference…I stand at 5’6″ (in sneakers) and so all of these fits are perfect for all the shorter guys out there.

Back to School Outfit Idea 1: THE CASUAL ALL-STAR

Color Palette: Monochrome

For the first back to school outfit we’re keeping things light and casual. Sure it’s the end of summer, but that doesn’t mean we have to jump into the darker hues of fall just yet. Personally, I love the simplicity of summer style and the clean silhouettes it encourages.

I’m a fan of the unbuttoned button up (or button down in this case) over top of a simple, solid colored t-shirt for an ultra-casual “I’m at play” kind of vibe. Take note of the chambray fabric. It’s a texture similar to linen and equally as appropriate for warmer weather. This back to school look will work for high school and college students alike.

You can even tuck in the front of your t-shirt and show off your stylish belt. The canvas belt is one of my summer staples. It’s versatile, pairing extremely well with a myriad of casual looks. A bonus detail is the handkerchief in the chest pocket. It provides a dash of style, but also functions as a cloth to wipe sweat from your forehead in the summer and autumn heat.

As for the pants, I’ve chosen light wash denim since it’s still summer. I love the transition in-between seasons because dark wash jeans is also a great choice. There are no rules, you can wear light wash in winter if you choose and dark wash in summer. Sometimes I like to give my jeans a roll or two depending on the type of look I’m going for, in this case, casual cool.

Finally for the footwear, I went with old school high-tops. I’ve never really styled Converse before, but a pair of timeless Chuck Taylors in black, white, navy or gray in this case is the perfect shoe for any stylish student.

Core Pieces:

• Basic tee
• Unbuttoned chambray shirt
• Rolled light wash denim
• High-top Converse All Stars aka Chuck Taylors

Back to School Outfit Idea 2: The Minimalist

Color Palette: Grayscale

Back to school outfit idea number two embodies the essence of “less is more.” If you want a simple stylish look, then look no further than your staple white t-shirt, tailored sweatpants (also known as joggers), and a pair of classic white sneakers.

Some would call this athleisure style while others would call it lazy, but one thing’s for sure, that it works because the fit is on point. Look at the silhouette, there are clean lines and no excess fabric on the three core articles of clothing in this getup.

The jacket has the same feeling as wearing sweats, but has the look of a tailored blazer. It makes for a bit of high-low aesthetic by elevating this ultra casual look ever so slightly.

White trainers are the ultimate casual shoe that can be worn with ultra-casual looks like this one all the way up tailored trousers and blazers or even suits. It’s trendy in 2018 and not going anywhere anytime soon so you can feel confident rocking those white sneaks.

Core Pieces:

• Clean white t-shirt
• Gray sweatpants
• Comfort jacket
• White sneakers

Back to School Outfit Idea 3: The Back to School Uniform

Color Palette: Autumnal

If there was one outfit that I had to wear to school everyday (if I were still in school), this would be it. There are several things at play with this personal uniform.

1. Tailoring
2. Simple color scheme
3. Proper fit
4. Casual vibes

These four elements combine to make for the perfect summer-to-fall transitional outfit.

The grey sweatshirt is a classic piece that’s athletic-inspired while still adhering to a smart casual dress code. While the navy J.Crew Factory Walker Vest provides stylish layering to help keep you warm during those cooler autumn days or freezing cold classrooms. A light quilted vest is one of my favorite layering pieces in the spring and fall seasons.

The blue stretch chinos are a unique shade that you don’t see many guys wearing. They fit well and taper towards the ankle which lends itself to a clean, modern aesthetic. A quick wrist check shows that I’m wearing the classic Timex Weekender with a custom, brown leather strap. It’s the perfect compliment to this casual uniform.

On my feet, I’m wearing the popular Nike Killshot 2 with the gumsole, one of my favorite casual sneakers to wear. Versatility is important when it comes to being stylish and these sneakers are as versatile as they come.

When it comes to fit, fabric and function, this back to school looks gets high marks.

Key Pieces:

• Cotton sweatshirt
• Light padded vest
• Tailored chinos
• Gumsole sneakers
• Classic watch

Back to School Outfit Idea 4: The Layered Legend

Color Palette: Autumnal

The final casual back to school outfit introduces a few fall elements. We’ve got autumn colors, a plaid flannel shirt layered over a lightweight henley up top, and a pair of classic desert boots down low.

You can add one more layer to this already stylish look by throwing on a dark or mid-wash denim jacket. This adds more character to an already masculine look. It feels a little bit rugged, but the tailored chinos balances things with a touch of refinement. If you’d prefer to go all-out rugged, then you can swap for a pair of selvedge denim with a rolled cuff. The beauty of this look is that you can remove layer after layer and still look like a stylish gent.

In my opinion, layering is one of the best ways to flex those sartorial muscles you’ve worked so hard to gain. You can go on looking like a legend in these streets if your layering game is on point.

The Clark’s desert boot is an iconic shoe that has become a fall staple in my closet. It’s masculine, versatile and has plenty of character after over a handful of seasons of wear.

One of the new additions to my watch collection is the Hamilton Khaki Field Watch in olive. It’s a clean timepiece from a heritage brand that I think compliments this getup quite nicely.

Core Pieces:

• Henley shirt
• Plaid flannel shirt
• Dark wash denim jacket
• Tailored chinos
• Clark’s desert boots
• Hamilton Field Watch

Related: Be sure to check out this post if you’re looking for some college dorm essentials.

Elements of Back to School Style Today

Based on current trends and forecasts for 2024, here are some key elements of back-to-school style for men:

1. Relaxed tailoring: Looser, more comfortable fits in trousers and shirts, moving away from skinny styles.
2. Varsity and collegiate-inspired pieces: Letterman jackets, rugby shirts, and sweater vests are making a comeback.
3. Sustainable and eco-friendly fashion: Increased focus on clothing made from recycled materials or produced through environmentally conscious methods.
4. 90s and Y2K revival: Baggy jeans, cargo pants, and oversized graphic tees inspired by turn-of-the-millennium aesthetics.
5. Smart casual blends: Mixing formal and casual elements, like pairing sneakers with tailored trousers.
6. Earth tones and muted colors: Shades of brown, green, and beige are popular, along with softer versions of primary colors.
7. Functional fashion: Emphasis on practical clothing with multiple pockets, weather-resistant materials, and versatile layering pieces.
8. Textured fabrics: Corduroy, fleece, and chunky knits add visual interest and warmth.
9. Statement outerwear: Bold jackets and coats as focal points of outfits.
10. Customization and personalization: DIY elements, patches, and personalized accessories to make styles unique.
11. Tech-integrated clothing: Items with built-in features for devices or enhanced functionality.
12. Gender-neutral options: More unisex styles and a general blurring of traditional gender lines in fashion.

Graduation

There you have it, 4 back to school outfits for men that you can experiment with today. Whether you’re in school or even if you aren’t, I hope these looks can help to inspire your casual style this fall.

Which of these back to school outfits are up your alley?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.