These are the top 4 men’s shoes for Spring that I really love. You’re probably not going to wear these with your Fall and Winter wardrobe, so it’s time to pull these shoes out of your closet and let them shine! Footwear is a great way to inject new life in your existing wardrobe, and these 4 shoes will make a stylish statement during Spring and Summer.
Here are my top 4 favorite shoes for Spring:
4. Suede Double Monk Straps
I included these in my Top 10 Essential Items for Spring as well. Suede Monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!
I absolutely love penny loafers. They look so good when worn with no-show socks and a little bit of ankle exposed. Whether you cuff your jeans or chinos, or hem your pants so there’s no break or a little ankle showing. A leather loafer looks so chic and luxurious. I love Ferragamo’s loafers (I got a pair for my fiancé Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.
Think of them as the middle ground between sneakers and penny loafers. They’re just as comfortable as sneakers, yet dressier like a penny loafer. I also included these in my Men’s Summer Essentials ebook because they work during the warmer months in general.
My hands down, favorite suede driving shoe is from Tod’s. Everything about that shoe – construction, design, and color choice – is so damn sexy and incredible. It’s worth every penny, and there is no close second for me.
Outside of your white sneakers, I love a great navy or grey low top sneaker. They’re neutral colors so you can wear them with everything you have and they definitely won’t get dirty quickly.
If you want to splurge, Common Projects makes my favorite sneakers and a close second are by Lanvin.
There’s only a few weeks of Winter left, so pretty soon we’re all going to have to start thinking about transitioning to our Spring wardrobe. So in addition to your year-round Men’s Essential staples that are already in your closet, Jordan O’Brien from The Gentlemans Cove and I each came up with a list of 10 Spring Essentials that every man should own.
My Top 10 Men’s Spring Essentials
1. Lightweight, Spring Suit
Whether you go with a linen, cotton, seersucker, or lightweight wool suit, these options will make a statement and keep you cool throughout the Spring and Summer months.
These lightweight blazers are perfect for casual Fridays at work or heading to lunch or dinner with friends. They’re a great way to insert a stylish statement while keeping cool. Linen will wrinkle a bit, but that’s part of its character so embrace it.
I love gingham shirts for the Spring because they can be worn dressed up with a suit or blazer or dressed down on their own or underneath a sweater. I included some great lavender, navy, and light grey gingham options below.
There’s no other brand that I love more than The Tie Bar. The quality, construction, and color/pattern choice can’t be beat by any other brand. Like I’ve always said, they’re not paying me to say this.
Polo shirts instantly make an outfit look more put together and Spring is the perfect time to start wearing them. I like John Varvatos, but be careful if you’re not in shape or have erect nipples because their silkier shirts will highlight these areas. The fit on Theory and Fred Perry polos is excellent and H&M is my go-to when I’m more price-conscious. You’ll need to replace those roughly every 8 weeks though due to fading.
Not only do short sleeve button-up shirts look stylish, but every man (regardless of age or body type) can wear these. There’s currently so many great options from J.Crew and come March/April, Topman will have an equally great selection.
I’ve maintained in some of my other videos and articles that you should save your suede for Spring. Well, it’s time to break out those items. I love the options below – you can choose from navy, light grey, and brown suede jackets. The A.P.C. jacket is a BIFL piece and will never go out of style.
Finally we’re entering ankle season, which means penny loafers can finally be worn. I love Ferragamo’s loafers (I got a pair for my fiance Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.
Suede monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!
Chinos should only be worn in Spring, Summer, and early Fall and that’s it. They’re a great alternative for those days when you don’t feel like wearing jeans and when you want to just feel cool and comfortable.
These as well as other great alternatives were included in my Summer Essentials E-Book. A lot of Jordan’s picks I actually included in that e-book so be sure to check it out if you haven’t already 🙂
Linen, as well as the other lightweight fabrics I also included in my list, is very breathable and will keep you cool during the warmer months. Here are some of my favorite items currently available.
Whether you need some extra sun protection or want to look stylish while staying cool, straw hats are super breathable and lightweight. Every year I get J.Crew’s panama hat, but it only lasts the season before it starts to fall apart. I’m currently eyeing Loro Piana, Brooks Brothers and Stetson’s hats because I know I can count on the quality and construction.
I like long sleeve henleys when they’re worn as a layering piece, so underneath a casual button down shirt paired with some dark wash jeans and boots or sneakers. If you’re a slim or wider gentleman, I highly advise against wearing henleys on their own because they emphasize your body size even more (and not in a good way).
If you’re new to wearing denim jackets, I suggest going with a black or dark grey version because it’ll be a lot easier to wear, especially if you wear jeans a lot because you don’t want to look like you’re wearing a Canadian tuxedo.
Let’s talk about my favorite and what I consider the best men’s dress shoes for Fall and Winter – Monk straps, Brogues, and Wingtips.
Quick note: Wingtips are technically Brogues, so I’ll be lumping them together throughout this article. Just know when I refer to Brogues that I also mean Wingtips.
I prefer these during the cooler parts of the year because they go much better with the heavier wool and cotton items you wear in your Fall and Winter outfits. Don’t get me wrong, they also work year-round, but I think there’s better options out there for the other parts of the year. Check out my Summer Essentials Ebook and Wardrobe Essentials Series for details about those options.
Below are the things I look for in a good pair of Monk Straps or Brogues.
MATERIAL
As I said in my Fall/Winter boots story, I love a good calf skin. Don’t get me wrong, I love a suede monk strap or brogue, as well, but if you live in an area with snow or rain, you’ll regret the day you wear them outside. So let’s wait to get into those until Spring or Summer.
SHAPE
I will say this about dress shoes until the day I die, but you want a nice, slim profile with a rounded toe box. Ain’t nobody got time for square or large, bulky toe boxes! – See the video near the top of the article if you’re unsure about what they look like.
COLOR
As for colors, I love a nice dark chocolaty brown, or even a medium brown, like a walnut. Black is also good, but the first color I’d get is brown because it goes better with all the Fall colors in your wardrobe. All these colors are represented in my suggestions at the bottom of this article.
SOLES
If you live somewhere with a bit of rain, ice or snow, then you can and should definitely have these with Dainite or rubber inset soles for added traction. If you don’t live in that kind of climate, then a regular leather bottom that you’ll find on 99% of dress shoes is perfectly acceptable, but I’d probably look for a Dainite or rubber insert sole as my default. There’s also lugged soles, which are pretty popular right now (and I included some in my selects below), but I have a feeling they won’t be around for the long haul. They’ve already come and gone with fashion a few times in my lifetime. When it comes to Fall/Winter boots, though, I love me a lugged sole.
MONK STRAP SPECIFICS
I prefer a double buckle because a single buckle looks less refined. (Example in the video at the top).
If you get black Monk Straps, make sure the buckle is silver, because gold or brass tends to look gaudy, but is perfectly fine on brown monks (examples in the video).
Also, please make sure the buckles are on the smaller side as opposed to some big ass buckles you’ll find on a colonial gentleman.
As for medallion toes and other flourishes, I like all of them, so check out my recommendations below.
These, to me, are the quintessential Brogue. If you’ve seen my other dress shoe article then you know my love of Allen Edmonds. They make amazing products with great value – and they don’t pay me to say that. I’m just a huge fan.
I love this color and the Dainite soles. They’re just perfection.
These hit all the points I look for in a double monk – the beautiful chocolaty brown with the matching soles, the silver hardware and the rubber tread inset for added traction. On top of that, they’re a GREAT price and my clients always comment about how comfortable they are. My other favorites are the Allen Edmonds Monks below, if you’re looking for something higher quality.
There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.
The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.
Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article.
The difference between dress and casual boots
Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.
Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.
My Requirements for a good Fall/Winter Boot
These items apply to all the types of boots – dress, casual and chukka boots:
1. A slim profile and not chunky
Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.
2. Plain, Cap Toe or Broguing
I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.
3. Lugged, Dainite or Rubber soles
These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.
4. Be brown or black leather
Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.
And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.
5. NOT be Suede
For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.
Can I wear boots with a suit?
Yes, but only when these 2 conditions are met:
You’re wearing a heavier wool or tweed suit. For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
Your pants are hemmed to have no break. The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.
How To Tie Your Boots
Check out my shoe and boot tying video for how to tie your shoelaces properly.
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