Trendsetting 101: Penny Loafers

These days, we are seeing the return of a lot of trends from the past. Welcome another one: penny loafers. Some of you probably haven't seen these since your school girl days. Well, the preppy staple is back. Those of you that swear by your driving moccasins, keep with it! Penny loafers are one of the 'it' shoes of the fall season. If you want to resist the trend or feeling like you are, consider what we did. They are a great alternative to your usual flats. If you focus on comfort, they are a great all-around shoe to have, for work and your off time. They also give you a touch of menswear, which looks polished and sharp. If the shoe still feels dated to you, go for a pair of loafer pumps, which is modern and different from the classic penny loafer flats. Stylists are coveting the loafer pump for fall. It's perfect for those of you who insist on a heel. Shall we get to how to wear the shoe now?

1. Go for ankle pants or skinny jeans:

We like the idea of flaunting the entire shoe, so we recommend ankle or cropped pants, straight leg or skinny jeans. If you can't get enough of your wide leg trousers (they are so in this season afterall), go for it. We just prefer a loafer pump in this instance, especially one in a fun color or stylish print that would peek out from your pants.

Our picks:
- J. Crew Pant, $80 + Zigi Soho Flat, $30
- Rich & Skinny Jeans, $98 + Michael Kors Loafer, $98
- Sanctuary Wide Leg, $99 + DVF Pumps, $280

Shop all: Ankle Pants | Skinny Denim | Penny Loafers

2. Continue the menswear inspiration:

Yes, we are channeling Annie Hall because there's nothing more perfect than topping off your penny loafers with menswear pieces -- items like blazers, tuxedo blouses, cloche hats, newsboy caps and messenger bags.

Our picks:
- Oasis Jacket, 121 + Merona Loafers, $25 + Bag, $81
- GAP Vest, $60 + RL Loafers, $79 + Cap, $40
- Brooks Brothers Shirtdress, $49 + Loafer Pumps, $129

Shop all: Menswear-inspired | Penny Loafers

3. Wear it with something girly:

You can also pull the opposite approach and temper a boyish penny loafer with a feminine piece. The outfit will be eclectic and unexpected. Ideas for girly touches could be floral or polka dot prints, lace or frilly fabrics or school girl charms like pleats, hearts, or peter pan collars.

Our picks:
- ASOS Skirt, $60 + Loafers, $295 + Necklace, $165
- Dolce Vita Floral Dress, $100 + Aldo Loafers, $60
- Topshop Blouse, $70 + Lucky Brand Wedges, $119

Shop all: Pleated Skirts | Peter Pan Collars | Loafer Pumps

4. Think "weekend look":

We also love wearing penny loafers with a look that's completely effortless; one that you could be in all weekend long, like a boyfriend cardigan, some jeans and a trendy scarf or a flannel shirt, jeans and a perfect-for-fall beanie. You could also go preppy with shorts and an easy polo shirt. If you feel comfortable and casual, you got the point.

Our picks:
- Isabella Oliver Cardi, $70 + Scarf, $24 + Loafers, $107
- Billabong Shirt, $45 + Jeans, $89 + Sperry Loafers, $80
- RL Polo, $50 + Khaki Shorts, $48 + Loafers, $62

Shop all: Cardigans | Scarfs | Penny Loafers

5. Throw on some tights:

Soon enough, we'll be entering sweater weather. Penny loafers look flawless with a pair of tights. Be sure to vary up the colors and textures you wear to add some interest and flair.

Our picks:
- HUE Textured Tights, $14 + Townsend Pumps, $60
- J. Crew Tights, $27 + Aldo 'Eda' Loafers, $50
- Express Tights, $17 + Ellen Tracy Patent Pumps, $89

Shop all: Tights | Penny Loafers



Trendsetting 101 is our new weekly series, centered on showing you how to wear the trends of the season. Come back next week for advice on another hot trend.

Spotted a trend out there that you want to try? Tell me what it is by leaving a comment below. I'll address it in a future post!


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