Join us for the ride today as we kick off another Online Shopping Picks entry — if you’re looking for the best men’s transitional footwear for spring, you’re in luck. What exactly do we mean when we say transitional? Well, we — and by we, I mean me — aren’t exactly talking about rugged winter boots or even classic summer sneakers. No, today we’re talking footwear that’s a touch more durable than your average set of kicks — maybe they combine a few different elements, like the cut of a chukka and the materials of a sneaker (see: Exhibit A, the SeaVees Huckberry Chukka). Or maybe, they’re both slightly dressy and yet suited for casual wear. Better yet, they should be relatively durable and versatile for fighting spring rain and looking great at the same time. So, you’ll see a solid mix below, from sleek suede chukkas to durable sneaker-boots and everything in between. If you agree with these picks — and even if you don’t — join me over on The Style Guide Facebook page to pick up what should be a lively #menswear discussion.
#1. Beckett Simonon Laval Suede Chukka Boots in Chestnut — $199
I’ve been fortunate enough to test out some Beckett Simonon footwear across the past few months, namely during a fall weekend in New York City. And the good news is that the brand’s chukkas are sturdy, sleek and extremely stylish. Such is the case with the Laval Suede Chukka Boot in a handsome shade of Chestnut. Pre-order these now and wait for them to arrive, because I’d wager you’ll want to wear them with everything from slim light wash denim to chinos. Oh, and an even better perk? The water-resistant suede, fit for taking on inclement weather.
#2. SeaVees Mariner Boot in Navy or Olive — $149.98
When it comes to talking transitional footwear, the Mariner Boot just might be the ideal pair to buy now — and wear very frequently when spring rains roll through. The end result of a collaboration between our pals at SeaVees and Taylor Stitch, the Mariner Boot features a British Ventile waterproof duck canvas upper for crucial spring protection. Plus, SeaVees’ signature herringbone tread outsole adds a nice dash of traction on wet streets, and the option to pick up either the Navy Mariner Boot or the Olive option bodes well for those of us who appreciate versatile footwear.
#3. AstorFlex Bitflex Chelsea Boot in Dark Khaki — $180
As seen in a Style Pick of the Week entry last fall, the Astorflex Bitflex Chelsea Boot has a lot going for it — it’s stylish and sustainably made, for one. And crucially, it combines both a relatively slim profile and a unique crepe rubber sole. Plus, who doesn’t love a great Chelsea boot? It’s an of-the-moment silhouette that’s transcended, well, trends, to become a footwear essential. And if you haven’t tried out a pair, this spring might be a good time to start. While they’re not water-resistant like the Beckett Simonon suede chukkas above, you still get nice quality & sharp looks.
#4. CLAE Hayward in Mojave Pig Suede — $100

Retro style meets functionality — waterproof suede and a neat silhouette.
The retro-style runner continues to have a moment in the menswear space — in other words, it’s simply an excellent-looking shoe style. If you love a great pair of sneakers, give the CLAE Hayward a look if you’re seeking a new way to shake up your spring footwear rotation. They’re certainly unique in both looks and functionality, incorporating waterproof suede with nylon side panels atop a crisp runner’s sole. Wear these guys with white jeans and a slim short-sleeve chambray shirt — plus a stylish denim jacket — on a breezy spring day, and you’re all set.
#5. OluKai Pahoa Boots in Black Seal/Brown — $200

Note the burnished leather, waxed laces and easily wearable design.
If you’re sensing a theme in this post — that of durable footwear that also looks sharp — then you’re right on the money. And the last entry on the list definitely falls underneath that umbrella. Comin’ at ya all the way from Hawaii, the OluKai Pahoa Boots feature some mixed-media design touches — note the contrasting upper and waxed cotton laces. What’s more, the footbed features EquilFit technology for comfort and performance. Not bad for a pair of leather chukka boots, ehh?
Honorable Mention: Thursday Boots Honey Suede Scout Chukka — $149
We’re bringing back the Honorable Mention category in these Online Shopping Picks posts, namely because it’s mighty tough to pick just five great pairs of stylish spring footwear. And when the final brand on the cut line is Thursday Boots, you can be darn sure we’ll give ’em a second look. Featuring a slick European-inspired silhouette and plenty of traction via a studded rubber outsole, these are dressy enough for the office and more than ready for Sunday brunch.
From start to finish, I hope you enjoyed this essential, excellent, even tremendous rundown of the best men’s transitional footwear for spring. Finding shoes that serve a purpose while providing comfort and functionality can sometimes be tricky — yet, plenty of brands are hitting that sweet spot quite nicely. From the water-resistant suede of the Laval Suede Chukka Boot to the toughness and on-point styling potential of the Mariner Boot, you’ve surely got options aplenty. If retro-inspired style is more your bag, grab the CLAE Hayward for a change, and I’d urge you not to pass up a pair of dressy-yet-versatile Chelsea boots (like the Astorflex Bitflex Chelsea Boot). Of course, who can resist yet another pair of suede chukkas, like the Thursday Boots Suede Scout Chukka? No one, that’s who. If you’ve got questions on how to style these boots or heck, if you should buy any of them, drop me a line via Twitter or in the comments below.
More importantly — stay stylish!
-Beau