The Helsinki is comprised of a leather upper, with classic stitching along the side panels and toe. The distressed leather finish gives a sophisticated elevation to the rugged make of the shoe, demonstrating elegance and function.

Believe it or not, the Helsinki from ECCO could even be used for a gentle hike or walk. The functionally built toe box allows for the feet to spread in comfort when walking, without restriction or pain. Built to last, the polyurethane soles can take a beating from dancing, hiking, or racing for a cab at the end of your evening. With their patented Comfort Fibre System, the ECCO allows for a cushion of air to circulate through the shoe, cutting down on odor and heat while providing a cushioned sole. If looking for something you won’t need to replace for a while, these are the best for you. The ECCO Helsinki may be a slip on, but the brand prides itself on the construction of durable, lasting footwear. A bit on the expensive side for our list, but still the average price of most similar styles, you can rest assured to invest in a pair of these for the long haul!

Handcrafted in Spain from beautifully tanned full grain leather, it uses the Bologna construction which is known for its comfort, and the cushioned feel it gives with every step. The Louie is lined with soft leather, offering a breathable environment for the foot, but one that doesn’t deteriorate with wear and that gets more comfortable with time.

The closures on the upper are made with quality hardware, allowing you to get a personalized fit over the instep. An almond shaped toe will allow for sufficient wiggle room at the front, while those with larger volume feet may find the wide option more suited to them. The sole is leather, with a rubber section on the heel that will help prevent signs of wear and deterioration. As for the price, it’s one of the highest on this list, so consider this pair of footwear to be an investment.

Well made footwear can sometimes be hard to find, but the President delivers on all accounts for a boot. The rubber studded sole gives added grip, and weather resistant treatment lets you step out without worrying about wet feet or ruined leather. An added bonus is that the boot is resoleable, should you wear them down as your new favorite boot!

An EVA strip and cork footbed give additional cushioning to each step, allowing you to stay out for the duration of the evening in comfort. As an ankle boot, lacing up gives added structure and stability to your foot and ankle, and flat wax laces keep you tied up for the evening. The President comes in on the more expensive side, but compared to other models of boots, is around an average price. Considering the styling and durability of the President, it’s still a great buy if you’re looking for a long-term investment.

Clarks has been designing stylish comfortable footwear since 1825. Throughout the years, they’ve employed innovative cushioning, 3D printing technology, and pride their brand on comfort through biomechanical assessments of the foot. Their oxford style shoe is no exception to this, boasting cushioned Ortholite insoles to keep your feet comfortable and dry.

Typical of an oxford style of shoe, Clarks has given their best selling model a rich leather look, with a cap toe to finish. Detail can be found in the stitching along the panels of the uppers and around the toe. With a great classical design, it’s a staple in anyone’s closet. The Clarks Tilden Oxford comes in at a moderate cost, but average when compared to other Oxford styles. However, knowing that you’re buying a product built for comfort may sway you to wear these out for that weekend wedding, to work, or even for just a night on the town.

The Midtown is a pair that will fit almost anyone, seeing that it combines smart sizing with a genuine leather upper. It comes in medium, wide and extra wide, which is great news for those who need a bit more space, while the upper is a natural material that breathes, flexes and adapts to the foot, especially once it’s broken in. To ensure your shoe retains its suppleness, make sure to take good care of it with a quality leather conditioner in the appropriate color.

There’s more to the fit of a pair than just the shape of the upper. How it will feel on your feet is highly dependent on the materials used in the sole as well, and this is where the Midtown shines. With a non-slip rubber outsole, it’ll keep you safe no matter the weather conditions, and the midsole features a good amount of OrthoLite cushioning that will absorb shock from standing and walking. With a price that’s average, and even low when compared to footwear of similar quality, the Florsheim Midtown is a definite top choice. It’s got everything going for it - looks, versatility, size options as well as technological innovation. It’s available in several colors and toe options, so you can easily find the perfect pair (or pairs) for you.

The upper of the Vylett is made with a satin material that looks luxe, and is the perfect choice for dressing up an ensemble. The large bow gives a pop of excitement, while the metal hardware (that matches the insole) provides a much needed contrast, that draws the eye to this part of the shoe.

Other things to keep in mind about this model is that the lining uses soft leather which is comfortable to wear even without hosiery, as well as the fact that the outsole is 100% resin which is more durable than traditional leather soles, and does much better with uneven and abrasive surfaces. As for keeping good care of this pair, all you will have to do to keep it clean is give it the occasional dab with a damp cloth. The cost association makes it a good investment, seeing that it ranks below average in price, but provides you with a comfortable, quality product.

The Total Motion comes in a number of options when it comes to color and upper material. Whether you prefer to go with a classic black, suede, leather or patent leather, or wish for something a bit more fashion forward such as leopard print canvas or studs, this heel by Rockport can give it to you. No matter which version you go with, you’re sure to be satisfied with the fit, looks, and ease of maintenance.

As any other pair of Rockport footwear, the Total Motion features many innovations that are meant to make it your go-to pair. From the truTECH® cushioning in the forefoot and heel which allow for excellent levels of shock absorption, to the high retention foam footbed that molds to your feet and provides great levels of lasting support, and even to the safety-oriented outsole that is stable and slip resistant. These have got it all. Fancy high heels can be crazy expensive, and if they’re cheap, it’s probably for a reason. However, the Rockport Total Motion heels surprise when it comes to price, which is not only affordable, it’s the cheapest out of all the items on this list! This is quite an achievement, considering that this is a genuine leather pair, made with excellent cushioning and comfort features.

In addition to the leather upper that will only get better with wear, the Jones features a leather lining and a leather outsole. This means that this is a high-end pair of boots, made to comfort and mold to your feet, and to serve you for years to come. You’ll find that these boots require a bit more love - you will need to condition the upper, let them dry thoroughly between wears, and have them resoled when the outsole wears out, but you’ll find yourself reaching for them time and time again.

The best footwear is constructed using the Goodyear welt method, which not only gives a great level of durability but also ensures that your shoes can stand up to more aggressive wear and that they can be easily resoled should the need arise. Do note, however, that due to having a leather outsole, the Jones shouldn’t be worn in wet weather, as this can damage the shoe. The Frye Jones is the most expensive pair of footwear on this list, costing a small fortune. This means that it may not be an option for most people, but those looking for something extremely high quality, that will work both with a suit and jeans, should consider getting these boots. They’ll serve you well, and for years, and they’re sure to turn some heads in the process.

This Venetian style loafer proudly gives an aristocratic feel to comfort. Vintage inspired leather designing mixes with comfortable sporty construction, giving flexibility to this slip-on shoe. A textured Vibram rubber sole allows for traction, perfect for boat attire or an afternoon on the docks. Plus, it’ll keep you safe on the dance floor too!

Cole Haan is known for its artisan quality of styling, bringing back a love for the 1920s generation gentleman. Since 1928, they’ve been bringing timeless formalwear to the masses, and their sporty Loafer is a classic for anyone’s footwear collection. Crafted with soft leather, moc-toe, and contrast stitching, it’s clear the classic details of a formal shoe were kept in this sportier option loafer. For a designer brand shoe, this hits the average mark on the price list. When comparing to other non-designer brand name shoes it may appear more expensive. However, the simple sporty design mixed with a formal sophistication makes this a good buy, especially as it can easily be dressed up or down.

Nothing is as elegant as a beautifully cared for leather shoe, and the Calvin Klein Brodie can do just that. Available in a number of leather types and colors, it’s an incredibly versatile shoe that will work with anything, from a suit, to a pair of chinos, and even with dressed up jeans. The lace-up closure allows for some fit customization, and the reinforced eyelets prevent wear and tear from lacing.

The padded footbed featured in the Calvin Klein Brodie helps to give you a softer feel on your feet that will make standing and walking more comfortable, even when they’ve been on your feet for hours. Expect to be out all evening without skipping a step in these shoes, but with a box toe, be sure to size correctly to suit your foot width. For a Designer brand name, The Calvin Klein Brodie is quite reasonably priced, coming in at just under average cost for a formal shoe. But if you’re looking to impress with Designer shoes, CK’s Brodie will not disappoint. The unique leather texture gives an added value to the shoe, different than other similar styles available on the market.