I've been wearing Dickies jackets for about fifteen years now, and honestly? They've become kind of my go-to for pretty much everything. Started wearing them back when I was doing construction work in college, and now I find myself reaching for them even when I'm just running errands or meeting friends for coffee.
Here's the thing about Dickies - they've got this weird ability to look good whether you're actually working or just pretending to be cool. And in 2025, they're still killing it. I mean, I see kids wearing them at the local skate park, my contractor buddy swears by them, and my sister (who works in marketing) has like three different styles hanging in her closet.
Why These Jackets Just Work
Look, I'm not going to pretend I understand all the technical stuff about fabric weaves or whatever. What I do know is that my oldest Dickies jacket - a basic work jacket I bought in - still looks decent. Sure, it's got some character marks now (coffee stain on the left pocket, small tear from when I caught it on a fence), but it's still functional. Actually, those imperfections kind of make it look better, if that makes sense.
The fit is... well, it's not slim-fit Instagram model territory. It's more like "I can actually move my arms and maybe wear a hoodie underneath if it gets cold." Which is perfect because who wants to feel restricted when they're trying to get stuff done? Plus, the boxy fit has somehow become trendy again. My younger cousin tells me it's called "oversized streetwear" now. Whatever works, I guess.
What really gets me is how these jackets transition between different situations. Last week I wore my black Dickies to a work meeting (threw it over a button-down), then kept it on when I stopped by the hardware store after. Didn't look out of place in either spot. That's pretty rare with clothing.
The Ones Actually Worth Buying
Fleece-Lined Hooded Nylon Jacket
This one's been my winter go-to for three years running. The fleece lining is surprisingly warm - like, I was skeptical at first because it doesn't look that thick, but it really works. Had it on during that weird cold snap we got in March, and I was comfortable walking around outside.
One weird thing though - the sleeves are definitely shorter than you'd expect. I'm 5'10" with pretty average proportions, and even the large feels a bit short in the arms. Not unwearable, just... you notice it. Especially if you're used to longer jackets. My girlfriend always comments on it when I wear this one.
The pockets are solid. Hand-warmer style on the outside, plus there's an inside pocket that's actually useful (not just decorative like some jackets). I keep my phone and keys in there usually.
Cambridge Bomber Jacket
Okay, this one's pricier than the others, but I get why people love it. My friend Jake has one and I borrowed it for a weekend trip last fall. The elastic waist thing is actually pretty smart - keeps cold air from sneaking up your back when you bend over or reach for stuff.
It's got this storm flap over the zipper that seems unnecessary until you're actually in rain. Then you realize it's genius. The hood stores in the collar, which is neat but honestly I never remember to check if it's tucked in properly before washing. Sometimes it comes out looking weird.
The only downside is that it's definitely more of an investment piece. If you're just looking for basic work outerwear, you can probably skip this one. But if you want something that feels a bit more premium, it's worth considering.
Generation Overhead Waterproof Jacket
This is the one for when weather gets serious. I don't own one personally, but my brother-in-law does roofing and swears by his. He's had it for two years and it still keeps him dry in pretty nasty conditions.
The kangaroo pocket is bigger than you'd think - he says he can fit his phone, wallet, and some small tools in there without it feeling bulky. The reflective details are actually visible too, not just decorative safety theater like some work gear.
Honestly, unless you're working outside regularly or live somewhere with really harsh weather, this might be overkill for casual wear. But if you need serious weather protection, this seems to be the way to go.
Designer Collaborations
I'll be honest - I was skeptical when Dickies started doing these fancy collaborations. Like, aren't they supposed to be practical work clothes? But I saw the Schott collection in person at a store in the city, and... okay, I get it now.
The materials feel noticeably different. More premium, I guess? The corduroy collar detail is actually pretty cool, and the wool lining feels luxurious in a way that regular Dickies don't. But we're talking about paying significantly more for what's essentially the same basic jacket with fancier materials.
If you're into fashion or collecting limited pieces, these make sense. For everyone else, probably not necessary. The regular versions do the job just fine.
Materials and Why They Matter
I'm not a fabric expert, but I've learned a few things through trial and error. The cotton twill ones are great if you like that broken-in feeling that gets better with time. My oldest jacket is cotton twill and it's gotten softer and more comfortable over the years.
The nylon ones are more practical in wet weather, obviously. They also tend to stay looking newer longer, which can be good or bad depending on what you're going for. Sometimes you want that worn-in look, sometimes you don't.
Polyester blends are easier to take care of. Less wrinkles, wash and wear kind of thing. They don't feel as "natural" as cotton, but they're definitely more convenient if you're not into spending time on garment care.
The construction quality is consistently good across all the materials I've tried. Zippers hold up well (though I did have one break after about four years of heavy use), pockets don't tear easily, and the stitching seems solid.
Getting the Right Size
This is where things get a bit tricky. Dickies sizing is mostly true to size, but there are some quirks you should know about.
First, those sleeves I mentioned earlier - it's not just the fleece-lined one. Most Dickies jackets seem to run a bit short in the arms. If you've got longer arms or just prefer more coverage, definitely size up. I learned this the hard way with my first jacket.
The body fit is roomier than a lot of modern clothing. This is great for layering or if you prefer not feeling restricted, but it might feel loose if you're used to fitted jackets. My sister always sizes down because she prefers a more tailored look.
If you're planning to wear thick sweaters underneath, definitely go up a size. The fleece lining provides enough warmth that you probably don't need heavy layers anyway, but it's good to have the option.
| What You Want | Size Recommendation |
|---|---|
| Regular fit | True to size |
| Longer sleeves | Size up |
| Layering room | Size up |
| Fitted look | Consider sizing down |
Where to Actually Buy These Things
The official Dickies website is obviously the safest bet for getting authentic stuff, but their selection online isn't always complete. Sometimes they don't have all colors or sizes available, which is frustrating.
I've had good luck with Backcountry and Zappos. Both have decent return policies, and the customer reviews are usually helpful for sizing questions. Zappos especially seems to have people who write detailed reviews about fit and durability.
Local workwear stores are underrated. There's a family-owned shop near me that carries Dickies, and the owner actually knows which styles work best for different jobs. Plus you can try stuff on, which is always better than guessing with online orders.
I've seen Dickies jackets popping up in more mainstream clothing stores lately too. Urban Outfitters had some last time I was there, though they were marked up pretty significantly compared to workwear retailers.
Making Them Last
I've probably made every care mistake possible with these jackets over the years, so here's what I've learned works (and what definitely doesn't).
Cold water washing is key. I ruined a jacket early on by throwing it in with hot water - it didn't exactly shrink, but the fit changed in a weird way. Now I always use cold water and it's been fine.
Don't put them in the dryer on high heat. I know it's tempting when you want to wear something quickly, but I've seen jackets get stiff and weird from too much heat. Air drying or low heat works much better.
For stains, deal with them quickly. Oil-based stains especially - I work on my car sometimes and learned this lesson the hard way. If you treat stains right away they usually come out, but if you let them set it's basically permanent.
The zippers are generally pretty tough, but don't force them if they get stuck. I keep a little graphite from a pencil around to lubricate zippers that start getting difficult. Works better than WD- and doesn't leave residue.
How They Stack Up Against Other Brands
I've tried Carhartt jackets too, and honestly they're built similarly well. Carhartt tends to be a bit pricier and maybe slightly more heavy-duty, but for most people the difference isn't huge. Dickies has better style variety though.
North Face and similar outdoor brands are in a different category entirely. More technical features, better weather protection, but also way more expensive and sometimes overkill for everyday use. Plus they often look more "outdoorsy" which doesn't always work for casual wear.
Regular bomber jackets from fashion brands can be hit or miss. Some are well-made, others fall apart quickly. Dickies gives you that bomber look with proven durability, usually at a lower price point.
Common Questions People Ask
Do they really run true to size?
Mostly yes, but those short sleeves are real. If you're between sizes or have longer arms, go bigger.
Can they handle really cold weather?
The fleece-lined ones are pretty warm, but if you're talking about serious winter conditions, you might need additional layers or a different jacket entirely.
How do I know I'm getting a real one?
Buy from known retailers. The fakes I've seen have cheaper feeling materials and the stitching quality is noticeably different.
Are they worth dry cleaning?
For regular jackets, probably not necessary. The care instructions work fine for machine washing. Save dry cleaning for the expensive collaborative pieces maybe.
Why are the collaborative ones so much more expensive?
Better materials, limited production, and brand premium. Whether that's worth it depends on how much you care about having something unique.
Final Thoughts
After wearing these jackets for so many years, I keep coming back to them because they just work. They're not the fanciest or most technical, but they hit this sweet spot of durability, style, and price that's hard to beat.
If you're looking for your first Dickies jacket, I'd probably start with one of the basic work jacket styles. See how you like the fit and feel before investing in the pricier options. And definitely size up if you're unsure - a slightly loose jacket is way better than one that's too tight in the sleeves.
The brand has definitely evolved beyond just workwear, but they haven't forgotten what made them popular in the first place. That's pretty rare these days. Most companies either stay stuck in the past or abandon their roots entirely when they try to modernize. Dickies seems to have found a way to do both.
Whether you need something for actual work or just want a jacket that looks good and lasts forever, you probably can't go wrong with Dickies. Just remember about those sleeves.
