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Chelsea boots via ASOS, with a bit of seasonal wear-and-tear. Learn how to style yours below, folks.

In case the headline wasn’t enough of an indicator, today we’re talking Chelsea boots on The Style Guide. Like other pieces that once seemed relatively trendy (remember when J. Crew  nearly single-handedly brought back the now-essential chambray shirt?), these guys have practically become a safe bet as far as a great footwear option for stylish guys. They’re not as hearty as a sturdy pair of winter boots, to be sure, but in the right style and color, they can definitely work in three seasons — and maybe four, if the snow holds out. The silhouette is generally sleek and sharp, and that seemingly goes for whether you pick ’em up in brown or black leather, or suede — all picks seen below. A bit of rocker edge never hurt anyone, either. And while at first it might take a while to get used to just slipping into a pair of boots — as it did for me — you might soon find they’re your go-to footwear option when you want to step away from leather sneakers, dress shoes or more military-inspired boots. Check out today’s Style Guide picks, and give us a look on Facebook for all the menswear content you can possibly ‘Like.’

#1. Thursday Boot Company Brown Duke Boot — $199

A reliable and (hopefully) hard-wearing pick from an upstart brand.

While it was an exceptionally close call between the Duke Boot and the Ellis Boot from Jack Erwin (option numero dos), a slightly lower price and more versatile brown leather swayed this writer (more readily wearable in winter, see?). Thursday Boots continues to be a solid option if you want to up your boot game for not a whole lot o’ dough, and they nearly always deliver. You get better quality than a pair of Chelsea boots from a fast retailer like H&M, yet you’re not ponying up an arm and a leg from a pricier brand. Added details like the studded rubber outsole should ensure a smooth grip no matter the season.

#2. Jack Erwin Ellis Chelsea Boot in Brown Suede — $220

Sleek and sturdy at the same time — a nice combination.

Perhaps it’s the thought of springtime being (hopefully) not too far off, but these beautiful Jack Erwin brown suede Chelsea boots end up near the top of this list for a few great reasons.  On the comfort end of the equation, these boots feature a rubber sole and full leather lining — both things you’ll be grateful for if you’re out and about a lot. And on the looks end of things, the suede appears rich and high-quality — take ’em for a spin with some white jeans when the time comes. Sure, they’ll require a little extra care and will probably be needed to shelved when heavy snow hits, but the rest of the time, they’re on the money.

#3. Wolverine 1883 Garrick Chelsea Boot — $175

Heritage-quality leather and rugged style details at an approachable price.

As sold by East Dane, these boots are part of Wolverine’s 1883 line, which has more than a dozen individual styles on the brand’s Web site. The biggest thing to note here is that, somewhat incredulously, you’re getting the Wolverine brand name for under $200 — no small feat when you look at the brand’s 1000 Mile line (particularly the Camden Chelsea Boot). At any rate, the Garrick is a slightly more rustic-looking Chelsea boot, what with burnishing details on the toe and heel, plus that wrinkled leather. These will still do just fine with dark denim or navy chinos, and they’d even add a nice contrast to spring denim.

#4. ASOS Tan Suede Chelsea Boot — $68.43

Dark tan suede Chelsea boots that combine some unique color with a terrific price.

Got an extra two quarters lying around? So these ASOS Chelsea boots are, it goes without saying, a downright steal for the price. And they’re another style that, like the Florsheim boots above, are a very worthy pickup if you’re looking to dip your toes into this trend. They’re cut a little lower on the heel for a slightly more continental look . Note that the suede isn’t the highest-quality, but it’s actually held up decently as part of a rotation and with less winter wear (the pair you see at the top of the page belong to yours truly — thanks Santa!).

#5. Florsheim Indie Gore Boot in Toffee — $99.90

More casual in nature thanks to the color and gore detailing.

Florsheim’s Indie Gore Boot has bit more going on visually than the typical Chelsea boot thanks to the side-gore detailing and the textured leather. Those aren’t all bad things, though. You’re getting a more casual pair of Chelsea boots — there is such a thing — for a great price. Feel free to beat these things up a bit; they’re the perfect pair to pick up if you’re just giving the silhouette a try. The Toffee color would sit nicely under some slim wool trousers now, and they’d work equally well under lightwash denim in the spring.

Putting together this list was quite tricky — it’s certainly no small feat to sort through Chelsea boot options when lauded retailers like Common Projects are throwing their (very minimal) hats in the ring. If you find yourself on an extreme budget but really want to go for the style, an option like H&M isn’t all bad for now, and more comfort-minded brands like Dr. Scholls are also producing Chelsea boots with a rugged edge. The biggest key to keep in mind is how you can make them work for you. If you find yourself wearing a lot of slim denim and mixing staples like tees with unconstructed blazers, the Chelsea boot is going to be a similarly slick style option. But if you need a more rugged pair of boots for crossing town, maybe save these guys for special occasions. Either way, it’s one footwear option I’d say you should give some thought to in the coming weeks — before everyone else beats you to the punch!

Stay stylish and happy shopping,

-Beau